This article is about Damon Salvatore from the TV Series. You may be looking for Damon Salvatore from the novels.
Look, what happened to Enzo is gonna haunt you and her for the rest of your lives. But the you standing with me right now, the you that's gonna marry Caroline Forbes tomorrow, the you that I have known for almost 200 years, you didn't do it. Evil, nasty, Ripper Stefan did it, and you are not him. You hear me?
In the 1950's, Damon was captured and tortured by the Augustine society, led by the Whitmore family, who experimented on vampires for a "bigger purpose". During his five years of captivity, he meets another prisoner, Enzo, with whom he became best friends with. Eventually, the plan the two made failed at a critical moment and thinking Enzo "died" because of him, Damon turned off his humanity to suppress the guilt and sadness. He sought revenge, an act of hunting down every member over generations which he finally ends with Aaron Whitmore's death.
Damon's sole purpose in coming back to Mystic Falls was to free his sire Katherine Pierce from a tomb she was never in. Damon deeply loved her after 145 years. After realizing that Katherine never loved him, his love for her fades as his friendship and love for Elena, Katherine's descendant and doppelgänger, grows. Due to her impact on him and the strengthening relationship with his brother, they begin working together to protect Elena, along with her friends and family. He lives with his brother Stefan, girlfriend Elena (when she wasn't away at college), and her brother Jeremy Gilbert (after Elena burned their house down) in the Salvatore Boarding House.
In the Season Three, Damon filled the role as a deuteragonist in the first half of the season due to Stefan falling prey to Klaus.
Throughout the series, his bond with Elena continuously grows and they eventually fall in love with each other. Shortly after her death and subsequent transition into a vampire, Elena's feelings for Damon are heightened which makes her admit her love for him and they start a romantic relationship in Season Four. The relationship is complicated when they realize that, due to the fact that it was Damon's blood that turned Elena, she is sire-bonded to him, so nobody is sure whether Elena's feelings for Damon are real or because of the sire bond, but most of the people they know insist that, once the sire bond is broken, Elena will return to Stefan. When Jeremy dies, Elena turns off her emotions; after she turns them back on, the sire bond is broken and Elena reveals that her feeling for Damon were real and she's still in love with him.
In Season Five, he discovers Enzo's undead status and they become friends once again however once "Elena" breaks up with him, he puts an end to his diabolical plan against the Whitmore Family and is then injected with a dangerous compound by Wes Maxfield, causing him to become an Augustine Vampire and the only one in existence. This injection would cause him to crave vampire blood and he would not be able to stop feeding until he had killed. He was later cured, thanks to Enzo, Stefan, and Caroline's actions. Due to the Other Side collapsing, Damon gave up his life to save his loved ones and this particularly caused Elena, Stefan, and Alaric much grief.
In Season Six, Damon and Bonnie are trapped in a 1994 Prison World, which Damon initially believes is his own personal hell, as they are continually reliving a day from his history that Damon believes is the worst thing he ever did. Bonnie is convinced her grandmother sent them there and there is a way out. They work together to find a way back to Mystic Falls. They also form an alliance to take down Kai. During this time, he is able to form a healthy friendship with Bonnie, and they are able to move on from their past and become friends. When Bonnie has a chance to send him home, leaving herself alone with Kai, she does so. Damon initially believes Bonnie was killed in the process, but when he realized she's still alive, he becomes determined to find a way to bring her back. After returning home, he learns that Elena has had Alaric compel away all her memories of their relationship and he attempts to win her back. Damon soon learns of Liz's sickness and soon after, she passes away in the hospital in front of him, leaving him devastated. He is soon reunited with Bonnie who made it out of the prison world and shows him a video of a mysterious lady, who turns out to be Damon's mother. Bonnie had managed to escape the 1994 Prison World by going to Nova Scotia and regaining her magic through Qetsiyah's calcified blood in Silas' tombstone. She also picked up the Cure for vampirism and gave it to him, who in turned gave it to Elena. He expressed the desire to take the Cure with her too and become human. At the end of the season Kai placed Elena into a sleeping curse and tied the spell to Bonnie's life, which was supposed to keep the now human Elena in a mystical coma until Bonnie dies; until then Elena would remain asleep. Damon was devastated by this and said a difficult goodbye to Elena as they locked her in a coffin while his best friend, Bonnie, lived out her remaining days.
As of Season Eight's I Was Feeling Epic, Bonnie managed to break the spell, allowing Elena to wake up, while not killing herself in the process due to the spell, and Damon being able to reunite with her. In the final flash forward, the newly human Damon married Elena Gilbert and they lived a long and happy life together before passing away and finding peace.
Damon Salvatore was born June 18, 1839, to Giuseppe Salvatore and Lillian Salvatore in what would eventually become the town of Mystic Falls, Virginia. He is the oldest and first born child of Giuseppe and Lillian. During his human years, Damon was seen and described to be rebellious, carefree, emotional, independent, troubled, insecure, misunderstood, principled, impulsive, competitive, and irresponsible and seemed to lack a general sense of direction. People of the town of Mystic Falls even described Damon to be irresponsible and cowardly, including his own father Giuseppe. The reason for this is because Damon rebelled against the town's and his own father's wish, by leaving the Confederacy on his own terms during the time of the Civil War. However, the reasons for Damon leaving the Confederacy is unknown. In his human years, when it came to love, Damon was always seen to be the chaser and the pursuer, the opposite of Stefan, who appeared to be harder to get and challenging with women, especially in regards to Katherine. Damon during his human years, also displayed womanizing tendencies with the opposite sex. Damon and his father, Giuseppe, never got along or had a good, close relationship and Giuseppe frequently expressed extreme disappointment and resentment in the elder Salvatore. Despite his very strained relationship with Giuseppe during his human life, Damon was very close to his younger brother Stefan and they shared a very close relationship and bond. Damon described Stefan as his best friend or companion and the person who trusted the most. However, the brothers eventually became strained after Katherine Pierce came into their lives and both brothers started to compete fiercely for Katherine's affections, with both of the brothers not being aware of Katherine playing them against one another. He was turned into a vampire in 1864, when he was 25 years old, after he drank Katherine Pierce's blood willingly and was shot by his father, Giuseppe, after attempting to save Katherine from being buried in the tomb.
When he was 12 years old, his father was very abusive towards him, burning him with a cigarret at a thanksgiving dinner. In his father eyes it was a lesson for his elder son, as he thought that Damon had stole his money. Damon, over a 150 years later, learned that it was his mother who stole Giuseppe's money in order to run from her abusive husband, and that she planned on taking Stefan and Damon with her, but the plan failed, as Giuseppe found out about it.
At the age of 17, in late May 1858, his mother died of consumption (he later learns in 2013 this was not the case). Damon had promised Stefan that he would write his mother's eulogy and say it at his mother's funeral. Just before the funeral, Damon comes to Stefan and helps him get dressed. Stefan says that father told him not to cry. Damon replies with that he is a child and that if he feels the need to cry that he is allowed. Saying all of this, Damon doesn't even go to the funeral. Instead he got wasted, returned to his younger brother who was angry with him for not showing up.
As a young man, Damon joined the Confederate Army on his father's order, to defend the South during the American Civil War. However, Damon secretly hated everything the South stood for, and had been planning to desert for sometime before his squad joined the army at Gettysburg. The only thing stopping Damon was fear of Giuseppe's disapproval. Eventually, he met a man named Oscar who convinced him to follow his own beliefs rather than his father's. That night, Damon deserted while his squad was decimated during the following battle.
It is uncertain how or when Damon found out that Katherine was a vampire, but unlike Stefan, he did not fear or reject her, and willingly drank her blood. She once demonstrated to him one of her tricks for securing victims, which was lying in the middle of a road to stop any travelers that may come to pass. Though he showed an initial hesitance, Damon even kissed her while a victim's blood still stained her lips.
Damon wanted to give up his human life and spend an eternity with Katherine, and he begged Stefan to keep the secret from their father, who was a member of the Town Council and a vampire-hater. When Stefan inadvertently revealed that Katherine was a vampire, she was taken away by the townspeople. Their father was furious and scolded Damon for trying to conceal her secret and protect her. Damon was furious with Stefan, but Stefan agreed to work with him to rescue her. In the midst of their daring plan, they were both shot and killed by Giuseppe, who was ashamed of his sons for sympathizing with and loving a vampire. They both died with Katherine's blood in their systems, but Damon awakened first and witnessed the burning of Fell's Church, where the townspeople had imprisoned the vampires, including Katherine.
When Stefan awoke the next morning, Damon told him that Katherine's death meant his reason for living was gone, and he wouldn't complete his transition into a vampire. Later that day, when Stefan returned after being unable to resist feeding on his own father, and inadvertently completing the transition, he forced Damon to drink from a young woman's neck, causing Damon to also complete his transition. He promised Stefan an eternity of misery, not for making him turn but for the fact that Katherine had turned Stefan as well, instead of just Damon. At some point Damon received a daylight ring from Emily Bennett. She told Damon that she had spared the vampires in the church, which Damon kept secret from Stefan until 145 years later, when he would be able to free Katherine from the church.
Damon saw Stefan in 1912 for the first time in 48 years since they transitioned; both had returned to Mystic Falls for their nephew's funeral. After an initial hesitance, Damon agreed to have a drink with Stefan and catch up. When he was feeding on a human alone, the vampire Sage found him and commented on his lack of enjoyment for the feed. Damon seemed content to feed just enough to survive, but Sage encouraged him to enjoy it, to take pleasure in being a vampire. Once he was persuaded, he tried to get Stefan to enjoy the feed, and talked him into feeding on human blood again. Stefan fed so hard on his victim that he tore her head off, shocking both brothers. Furious with Damon for making him drink human blood, he ran off and Damon did not pursue him.
Damon was living in New Orleans with a vampire he had turned named Charlotte. Damon soon noticed a pattern of strange behavior from the woman, in that every order he gave her, even seemingly innocuous ones, she followed with frightening enthusiasm. He sought guidance from the witch Valerie LaMarche to break the Sire Bond between him and Charlotte, and the witch told him she needed a human sacrifice of 12 people to do the spell. Damon killed the 12 people, but could not find Val to perform the spell he needed. He ended up ordering Charlotte to count every brick on every building in New Orleans and meet him at the corner of Bourbon and Dumaine. He left New Orleans soon after...
Stefan and Lexi found Damon while he was in New Orleans. At Lexi's insistence, Stefan sought to make peace with his brother before shipping out to the North African front of the war. After an initial hesitance, Damon seemed happy to reunite with his brother after thirty years apart, and the two spent the evening talking. Damon even suggested he might join Stefan and leave for war with him, but Lexi made it clear she did not approve of the idea. Her concerns seemed warranted especially after Charlotte brought a bleeding victim to the bar where they were talking and Stefan started to lose it at the sight and smell of human blood. Later, Damon was all ready to ship out with Stefan when Lexi talked him out of it, citing his profligate lifestyle and how Damon's behavior would not be good for Stefan's rehabilitation. Realizing she might be right, Damon decided not to go, and he left the train station without explaining to Stefan.
In 1953, Joseph Salvatore lured Damon to Mystic Falls in order to hand him over to Dr. Whitmore. After Joseph injected Damon with vervain, Damon killed him, but Dr. Whitmore entered the room shortly after and injected Damon with another dose of vervain. When he woke up he was strapped to a table and Dr. Whitmore cut one of his eyes out, in order to experiment and study vampire healing abilities. Damon was brought to a cell and in the cell next to him was another vampire named Enzo. The two vampires bonded and it was Enzo's friendship that allowed Damon to hold on to his humanity. Dr. Whitmore continued to torture and perform experiments on him and he called him 21051.
Every year Whitmore would show the rest of Augustine Damon and Enzo and demonstrate his research on the annual New Years Party. Enzo then came up with a plan for one of them two would drink the others blood ration in order to build up his strength until the coming New Years Eve. Damon was the lucky one and when the next New Years Eve Party came he broke free from his chains and he slaughtered every member of Augustine while the building set ablaze. Enzo was still trapped in his cage and Damon tried to free him, but the cage bars were soaked with vervain and couldn't get him out. Damon knew that if he was going to save himself he had to stop caring about Enzo so he turned his humanity switch of. Now not caring he left Enzo to burn alive. After finally being free from five years of torture, Damon kept the promise he made to Enzo to kill every member in the Whitmore family, but one and let that person have a family and kill them to but one and to the same thing again and again. Damon did exactly that and among the ones he killed was Aaron Whitmore's parents and Aaron was among the ones that he kept alive.
It had been two years since Damon escaped the Augustine cell, and he still had his humanity switched off. On November 8, 1960, during Election night, a lady asked Damon for a interview. She asked him questions related to the terrible fire at Whitmore House and then tried to attack him with a vervain injection, but Damon easily stopped her. When he found out that she was an Augustine member he ripped her head off. Decades later Damon finds out that the girl he killed was actually Enzo's one true love, Maggie James.
Damon lived in New York City during the 70's, where he maintained a wild life full of parties and feeding off of people. At the time, he still had his humanity switch off and he killed locals of New York; a soon to be fed upon victim asked if he was the Son of Sam, to which Damon replied, "Son of Giuseppe, but close enough". Damon was friends with Will, another vampire, who ran a bar and let Damon feed on the people there, while in exchange, Damon stole his victim's ID's for him.
Lexi had eventually found Damon and told him that she and Stefan had heard all about Damon's current life and that Stefan was worried for him. Lexi tried to help Damon get his humanity back, but Damon rejected her offer. However, Lexi was stubborn and she stuck with Damon for the following six months. She had gotten Damon to talk about Katherine Pierce, thinking that if he talks about her, his switch will flip on. Damon tricks Lexi into thinking that his humanity was back and the two have a night full of wild sex.
The next morning, Lexi woke up on a roof because the sunlight was burning her skin. She tried to escape by opening the door to get into Billy's, but it was locked. Then she found out the truth: Damon had tricked her. Damon told her that it was his way of getting back at her for annoying him for the past six months. He ditched Lexi on the roof thereafter, leaving her trapped until nightfall. It was revealed in The Cell, that Damon turned off his humanity in the 1950's because he couldn't deal with the pain of leaving Enzo behind while escaping from the Augustine Society.
In April 1994 (after Kurt Cobain died) , Damon with his humanity still off, shows up on Stefan's doorstep, wanting to make amends. Zach Salvatore, the owner of the house and their nephew, allows Damon in on Stefan's promise that he'll keep him in line. Zach has been living with Gail who is pregnant with his child. Stefan warns Damon to stay away from them claiming that both of them are on vervain.
One day, at a party, Damon flirts with a young Liz Forbes. Stefan takes a picture of Zach and Gail and notices bite marks on Gail's wrist. He then confronts Damon about feeding on Gail and after Damon compels Liz to forget ever meeting him, Damon breezily confesses that he swapped out Zach and Gail's vervained coffee for a little in-house feeding. An angry Stefan reminds Damon that these people trust them and then snaps his neck.
Damon wakes up in the shed without his daylight ring. Stefan wants to know what Damon's really doing there, and Damon says he wanted to feel a connection to his humanity again. He tries to convince Stefan to go on a road trip with him. Instead, Stefan reminds Damon of all the times he's ruined his life and how he can't seem to help doing it. Damon gets it that its a no for a road trip then.
On May 10, 1994, Stefan and Zach hear screams and rush to the library to find bodies everywhere and Damon covered in blood, holding Gail hostage. He demands his daylight ring back from Stefan, who returns it, realizing he'll never be rid of Damon. Damon gives his own version of their past. Damon says, "In 1912, I showed you who you were, Stefan. In 1942 I gave you your freedom and in 1977 I almost killed your best friend because it should have been you there to help me. You owe me. It'll take you an eternity to pay me back.". Then he kills Gail by attacking her and leaves.
Damon turns a woman named Isobel into a vampire after she asked to be turned by him. He will later meet and fall in love with her daughter Elena Gilbert who will also be turned into a vampire by his blood but not on purpose.
Throughout The Vampire Diaries Series
Upon arriving in Mystic Falls, Damon torments his brother Stefan by constantly threatening Stefan's new love interest, Elena Gilbert. He remarks that Elena is a "dead ringer" for the brothers' former shared love, Katherine Pierce. He also displays his strength in comparison with Stefan, pointing out how much of a disadvantage it is for Stefan to drink only animal blood.
In Pilot, Damon claims his first two victims at the very opening of the episode but makes his presence known in a more theatrical way by attacking Vicki Donovan in the woods. Later, when Elena visits the Salvatore Boarding House in search of Stefan, Damon is there instead, and he implies that his brother is on the "rebound" from a recently lost love. When Elena leaves, Damon taunts Stefan because it is harder for him to effectively compel Vicki Donovan to forget a vampire attacked her. In the end of The Night of the Comet, Damon charms and beds young Caroline Forbes, a friend of Elena's, ending the night by viciously biting her neck and feeding from her.
In Friday Night Bites, Damon drives Caroline to her cheerleading practice, having compelled her to keep his secret and to be unafraid of him. He also takes her to dinner at Elena’s house, antagonizing Stefan as he continues to fill Elena's head with lies about Katherine. Elena surprises him by asking which one of the Salvatores dated Katherine first, and she renders him speechless by telling him that she was sorry, because he lost her, too. Later that same night, Damon follows Elena to the parking lot before the football game and attempts to compel her to kiss him, but due to her Vervain necklace, she is free of his influence and slaps him in the face. Angered, Damon confronts Stefan on his way to the field, but he's further enraged when Stefan claims that he still has humanity in him. Damon responds by killing William Tanner, who is Stefan's football coach and teacher of Elena. That night, when Stefan is writing about how there is nothing good left in Damon, Damon is in Elena’s room, gazing at her and stroking her cheek.
In Family Ties, Damon wakes Stefan by manipulating his dreams and creating a nightmare in which Elena becomes the older Salvatore’s next victim. He claims that he can do this because of Stefan’s animal blood diet. Stefan responds by throwing a knife into Damon's chest, something Damon doesn't seem to feel, and though Damon admits he deserves it, he later stabs Stefan back for ruining one of his John Varvatos shirts. He also used a large mountain lion to cover up his murders, saying he would be staying in town for a while. He's later shown lounging in Caroline's room reading a book from the Twilight series, expressing his distaste for how ‘whipped’ the character Edward is. When asked why he doesn't ‘sparkle’ in the sun, he replies that he has a ring, and that it protects him. Caroline wonders if the bite-marks covering her body will turn her into a vampire, and Damon describes the process of turning as an ‘ordeal,’ explaining it to her casually. Damon also reveals his extreme disregard for human life in this episode: When Caroline asks him if he’s going to kill her, he calmly tells her that he will, but not yet. Later in this same episode, Damon is reading on the couch when Zach approaches, asking him why he’s in Mystic Falls. When Zach angers him by saying that he always has a motive, Damon holds him up by his neck, further displaying his volatile personality. Stefan arrives to spare Zach before Damon kills him. Damon also expresses his pleasure with never growing old while getting ready to attend the Founder's Party. He nearly drinks alcohol spiked with Vervain, a part of Stefan’s plan to disable him, and remarks that, going to the party angry, “Who knows what I'll do?” At the party, Damon is first invited into the Lockwood Mansion by Carol Lockwood. He appears behind Stefan and Elena just as Elena is reading both of their names on the original registry for the First Founder's Party. Elena expresses interest in hearing more about Stefan and Damon's lineage and, as he's compelled her to distract Stefan, Caroline requests to dance with the younger Salvatore. Left alone with Elena, Damon begins with a very mocking apology, and he spins a tale about the ‘original’ Salvatore brothers. He says that someone they loved very much was burned in the church during the Battle of Willow Creek, and that when the brothers went to rescue the woman, they were both shot. Later, Damon leads Caroline upstairs and takes a yellow crystal from a secret compartment in one of the objects on displays; a large wooden box. He says he put it there a long time ago. He seems to blend into the party until Elena sees the bites on Caroline's back and confronts him, threatening to go to Caroline's mother. Angered by this, Damon takes Caroline out near the lake. He claims to forgive her, but then says he’s over her and bites her neck. He didn't realize that Stefan had spiked her drink while dancing with her, and that he'd just consumed enough Vervain to render him harmless. Stefan took him back to the Salvatore mansion, injected him with more vervain, and locked him in the dungeon under their home.
In You're Undead To Me, Damon manages to establish a weak mental connection to Caroline, despite being locked in the dungeon under Salvatore Boarding House. He contacts her first in her room, though this proved rather ineffective, and then again in the hallway at Mystic Falls High School, while she was getting more towels for the Car Wash. She comes all the way to the boarding house and attempts to release Damon, though Zach tries to keep him locked up. Damon snaps Zach's neck and chases Caroline through the house, though he's severely weakened and unable to walk in the sun because Stefan took his daylight ring. He waits until nightfall to stalk a group of young people, including former victim Vicki Donovan, and kill all of them, excluding Vicki herself.
In Lost Girls continues with Damon feeding on his new victims and burning their corpses, using one of their arms to wipe the blood from his mouth. Strangely enough, these actions were performed outside of a crypt with the word ‘Salvatore’ carved in it. Damon calls Stefan as he burns the dead, demanding to have his daylight ring returned, going so far as to threaten Elena’s life.
After hanging up with Stefan, Damon finds that one body isn't burning, but when he goes to set her on fire, he realized that Vicki is still alive. Damon seems intrigued by her resilience, and he takes her back to the Salvatore Boarding House, where he feeds her his blood to heal her. This episode (during Stefan's story to Elena), also shows Damon and Stefan playing an early version of football in front of their home in 1864, only to be interrupted by Katherine. In the present, Damon feeds Vicki more of his blood while also feeding on her, and the two of their get drunk together and begin dancing around the house. They end up in Stefan's room, where Damon tears things from their places as he moves around. The two start slow-dancing, at which point Damon snaps Vicki’s neck. When she wakes up, he tells her that she must feed to completely the ‘process,’ but, smiling, he suggests she go to Jeremy's house, where he knows Elena will be. He even shows up there later, forcing his way inside and sarcastically warning Elena about who she invites in. When Stefan is shot by Logan Fell, who was using the Gilbert Compass to track down vampires, Damon appears, kills Logan, and extracts the wooden bullet from Stefan's chest, though he demands to have his daylight ring back. He seems uncaring when Vicki feeds on Logan’s body, completing her transition into a vampire.
In Haunted, when Stefan is trying to help Vicki adjust to her new life, Damon acts offended that the murder of Logan Fell isn't in the newspaper, and he says that someone is covering it up. He also tells Vicki about the compass he took from Logan. He also taunts Stefan about giving Vicki animal blood, and when he opens the front door to find Elena standing there, he acts arrogantly toward her. Later in the episode, Damon invites Vicki outside, where the Salvatores lose her in the forest, and while the events at the Halloween Party take place, Damon sits down with Carol Lockwood. When he tells her his last name, she wonders if there is a relation to Zach Salvatore, but when he attempts to compel her to tell him how she knows Zach, he realizes she's wearing a vervain bracelet, which keeps him out of her mind. He doesn't relent in his quest for information, mentioning the vervain to get Carol talking freely to him. When she mentions the Town Council, Damon seems interested, but Carol quickly changes the subject. Damon continues his relentless flirting and manages to find out how they’re eliminating names on the ‘vampire suspect’ list: Anyone who arrived at the Founder's Party during the day was eliminated, which would include Damon and Stefan. He offers to escort her to the school, where he runs into Bonnie. He asks her where Caroline is specifically to antagonize her, but then he realizes she's wearing the yellow crystal he took it at the Founder’s Party. He tries to take it, but it burns his hand when he touches it and Bonnie runs away from him. Stefan calls Damon after he’s forced to stake Vicki, and when Damon shows up, he finds Elena sitting beside her body. His cool demeanor enrages Elena and she tries to hit him, but he catches her hand. He tells her that none of this matters to him, so when he releases her, she slaps him. Damon seems angered, but he remains calm as he tells her that she needs to leave because of the blood coming from her wounds. He later shows up on Elena's porch, offering to erase Jeremy's memory because Stefan's diet prevents him from effectively compelling humans. Elena accepts his offer in order to help "Jer".
In 162 Candles, Damon first appears beside Stefan’s napping guest, Lexi Branson, who has come to town for Stefan's birthday. She expresses immediate displeasure when she sees him, remarking that he’s “only the bad parts” of being a vampire. When he gets too close, Lexi pins him to the bed and tells him not to ruin her time with Stefan, threatening him with bodily harm. He later goes to Sheriff Forbes' office to deliver a package of vervain, supposedly in Zach’s stead. Damon uses this to get more facts about the Founder's Council, and to put himself in their ‘small circle.’ He also encounters Caroline at the school and compels her to throw a party at the grill so he can make sure Stefan and Lexi show up. He speaks to Elena, who has concerns about what he compelled Jeremy to believe, though he insists that he only “took away his suffering."
To further antagonize his brother and give the Town Council a scapegoat, Damon kills a man in the alley near the Mystic Grill and compels a woman to tell everyone it was Lexi that killed her companion. When they remove Lexi from the bar, she breaks free of the sheriffs and attempts to kill Sheriff Forbes, who repeatedly shoots her in the chest. Damon arrives and stakes her, much to the shock and surprise of Stefan and Elena. Stefan later attacks Damon in their home and stakes him in the stomach, which, for a moment, makes Damon believe that his brother actually killed him. Stefan says he's only sparing him because he saved his life, but he's done with him.
In History Repeating, Damon shows regret for killing Lexi and attempts to apologize to Stefan, declaring he won’t feed on a human for at least a week. While the two are sarcastically impersonating one another, Stefan tries to get Damon to tell him why he's returned to Mystic Falls. Damon immediately shuts down and leaves, taunting Stefan once more on his way out. Later in the day, Damon steps up his harassment of Bonnie in an attempt to get his yellow crystal back. He also reveals that he knew Bonnie's ancestor Emily Bennett, who has been haunting Bonnie through her dreams. He tells Bonnie to relay to Emily that “a deal’s a deal.” When he encounters Stefan at the Mystic Grill later, he refers to Stefan's personality as a ‘lesser place’ while impersonating him. The two brothers engage in a game of darts, where Stefan continually tries to get the truth out of Damon.
They also play a short game of football, during which Stefan tries to convince his brother that their love for Katherine wasn't real. He asks Damon what he wants with Katherine's crystal (the yellow crystal he'd been pursuing so long), and Stefan also reveals that he was the last one to see Katherine the night she was taken away. Damon finally reveals his motivation for returning to their birthplace: “I'm gonna bring her back.” He explains that he went to the witch Emily Bennett and begged her to spare Katherine, so the witch magically sealed Katherine in a tomb beneath Fell's Church. He also says that, in order to gather the power into the crystal, Emily used the comet passing overhead that night. Damon even says that the only reason he didn't kill Bonnie to take the crystal is because he promised Emily he would protect her family. When Elena calls Stefan to tell him about Bonnie leaving with the crystal, Damon overhears and vanishes from behind his brother. He confronts Emily (in Bonnie's body) in the woods near Fell's Church. When he nears her, she uses magic to throw him into a tree, where he’s speared by a broken tree branch. Stefan arrives and pulls Damon down, but he's shocked to learn that instead of just Katherine, Emily saved twenty-seven vampires in the tomb, which is the reason she stands in the center of the clearing and destroys the crystal. Emily immediately leaves Bonnie's body, but, enraged, Damon bites her. He's seen in the background, grieving the destruction of the crystal, apparently in a state of shock. He's seen again in the very end of the episode, sitting by the church staring sadly into space.
In The Turning Point, Damon and Stefan seem to have decided to leave Mystic Falls, but Damon continues to be humorous about it, suggesting they try out for the ‘Amazing Race.’ Sheriff Forbes rings the doorbell while they talk, requesting to speak to Damon. She tells him of another vampire attack and asks him what he thinks they should do. The moment he re-enters the house, Stefan assumes that he’s killed someone, but Damon denies it. He taunts Stefan by seeming to care little about the ‘new vampire in town’: “What do we care? We’re leaving anyway, right?” Not following his own humor, Damon gets Caroline to use the Gilbert Compass to track down the vampire, and they end up at an abandoned warehouse.
Damon enters, but is shot multiple times by the newly transitioned Logan Fell, who accuses Damon of turning him into a vampire. Logan keeps him there, questioning him about vampires, but Damon refuses to tell him how he can walk in the sun. After Logan leaves, Stefan and Damon talk on the phone and Damon tells Stefan what happened to him in the warehouse. The two brothers team up and ambush Logan, who has kidnapped Caroline and planned to turn her into a vampire. After Stefan leaves, Damon interrogates Logan and Logan reveals that he knows about the tomb beneath the church. Expressing interest but pressed for time, Damon tells him to pretend to attack him and then get away so they can meet up later. When Damon goes to the church to meet him, he's shocked by a call from Sheriff Forbes, who thanks him for leaving Logan's body.
In Bloodlines, Damon starts of the episode with a bang when he rescues Elena from her crashed SUV. When she awakens, Damon reveals that they're in Georgia. He takes her to Bree's Bar, where he reveals that he's known Bree since she was a college freshman, and that she's a witch. While Elena’s on the phone, Damon questions Bree about another way to open the tomb, and he’s disappointed to find that there is no other way. When she calls Stefan, Damon goes outside and asks if she's okay, to which she responds, cautiously, “Don't pretend to care.” Inside, the two both eat a plate of fries with a burger while Damon explains that Elena can’t possibly be descended from Katherine, because Katherine never had a child.
He also tells her that vampires can't procreate, and that as long as he keeps a healthy supply of blood in his system, his body functions normally (to digest human food). The two end up getting drunk together and doing shots at the bar, where Elena gets very, very intoxicated. Damon's later seen at the bar, where Bree asks him where Elena is. She seems to have vanished, but when Damon goes looking for her, he falls into the trap of Lexi's vengeful vampire boyfriend, who was originally understood to be human. Elena manages to save Damon's life by talking about Lexi, but, angry that Bree betrayed him and sent the vampire to kill him, Damon goes back to Bree’s Bar and confronts her. She attempts to spare her life by telling Damon that there is one more way to get into the tomb, through Emily’s Grimoire, essentially the book she uses to write down her spells. Damon kills by ripping her heart out. On the ride home, Elena points out that she saved Damon’s life. At the very end of the episode, Damon goes to the Mystic Grill and requests a bourbon at the bar, where the new history teacher Alaric Saltzman also happens to be sitting. Alaric has a flashback of Damon killing his wife, Isobel.
In Unpleasantville, Damon is first seen rummaging through the Salvatore library, where Stefan confronts Damon for taking Elena to Georgia. He later encounters Bonnie at the Mystic Grill, saying “we need a fresh start.” She warns him to stay away from her, but the conversation is ended by Ben McKittrick, who comes to Bonnie's ‘rescue.’ Later he's seen writing the names of the town's founders, and Stefan brings him their father's journal, saying he knew Damon was looking for it. Stefan assures him that the journal has nothing helpful in it, but offers his help to Damon if only Damon will leave Mystic Falls. Suspicious of his motives, Damon rejects his offer. Damon also answers Stefan’s phone when Elena calls, telling her that Stefan is on his way (relieving her worry that another vampire is in her home).
Damon comes over after Elena is attacked, and the two of them, realizing that he was invited in and therefore able to harm her at any time, decide to go to the 50's Decade Dance to hunt the vampire down. Alaric notices Damon enter with Elena and Stefan. Damon later sarcastically asks Bonnie to dance, though he still seems to be trying to reconcile with her. He then asks Elena to dance, but she dances with Stefan instead. While Damon is watching the two of them dance, he's approached by Alaric, who wonders about his presence there. He asks Damon a long series of questions, but when they become too personal, Damon becomes suspicious and stops answering, which leads to Alaric leaving. Damon’s seen dancing with a blonde girl later, and Elena remarks, “You really can't take him anywhere, can you?” When her vampire stalker attacks her, Damon and Stefan come to Elena's rescue, but Damon notices Alaric lingering near the cafeteria door. When he confronts him, he attempts to compel him to tell him what he knows, and satisfied that he knows nothing, Damon leaves him there. It is revealed that Alaric has Vervain crushed in his fist to keep Damon out of his mind, indicating that he was prepared for Damon to confront him.
In Children of the Damned, Damon is first seen in a flashback to 1864, where he and Katherine feed on a stagecoach full of people. In the present, Damon is sitting on the end of Stefan’s bed when Stefan and Elena wake up, happy to team up with them. He tells them they need to find Johnathan Gilbert's Journal, which will hold the location of the Grimoire. In flashbacks, Damon is revealed to have a particular distaste for his father's opinion, while in the present, he's in the Gilbert House talking to Jenna Sommers. When Elena arrives, the two of them talk in the kitchen, and Damon questions the absence of Stefan. He asks Elena if he can trust Stefan’s help, asking her, for once, without sarcasm.
This episode flashes again to Stefan and Damon in 1864, when Damon's trust for Stefan was first broken. In the present, he and Jeremy are playing a video game. Stefan arrives and tells him that the Gilbert Journal was missing. Damon realizes that Jeremy also knew where the journal was, so he asks him who he showed it to. When he reveals that Anna knew about the journal, Damon takes him to meet her at the Grill. Damon follows Anna back to her hotel room and attacks her, but as they're at equal strength, he relents and they both release each other. While Elena and Stefan are digging up Giuseppe Salvatore's grave, Damon realizes that the grimoire will be in his father's grave. He confronts Stefan and Elena at the grave, finding that they've betrayed him and they were going to stop him from bringing Katherine back. Damon declares that he can only trust himself, though he seems hurt by the fact that Elena had him fooled (earlier she told him he could trust her). In order to get the grimoire from Stefan, Damon feeds Elena his blood and threatens to turn her into a vampire. Once he has the book, the others leave and Damon recalls how he and Stefan were both killed trying to save Katherine.
In Fool Me Once, Stefan comes to Damon after Elena is kidnapped, but Damon refuses to help, not even giving up the location of Anna's motel room. He tells Stefan that he hopes Elena dies. He goes to Bonnie's grandmother, Sheila Bennett, looking for Bonnie, but when he threatens her, she uses her magic to immobilize him. Anna suggests that Damon and she work together, but when she threatens Elena's life, he agrees to it. When Elena comes to Damon later, requesting they work together again, she takes off her vervain necklace so he'll know she's honest. She also asks him why he didn't use compulsion on her in Georgia, to which Damon replies, “I wanted it to be real.”
He puts her necklace back on and tells her that he's going to trust her. They gather in the tomb, and when the door is finally opened, Damon takes Elena inside to make sure they won't close the door back on him. He searches the inside with a blood-bag in his hand for Katherine, and he's devastated and enraged to find that she's not there. He throws the blood at the wall, where it splatters, and he nearly refuses to leave the tomb. It takes both Stefan and Elena to coax him outside, where he stares vacantly into space. Elena comes over and says that she's sorry, and she hugs him, though he seems too numb to react. He later appears in Anna's hotel room, threatening her mother, Pearl, who was retrieved from the tomb, and confronting Anna about knowing Katherine wasn’t in the tomb. Pearl tells him that Katherine got away, and Anna points out that Katherine always knew where he was, but didn't care. Stefan finds his older brother sitting by the fire, staring into the flames. He sits nearby, but doesn't speak.
In A Few Good Men, Damon is in a take of near-constant intoxication, indulging in compelled college girls with loud rock music playing in the Salvatore Boarding House. When confronted by Stefan, Damon gives him a drunken speech about freedom, claiming that he's perfectly alright. Stefan questions him about a woman named Isobel, though Damon doesn't seem to remember her. He says “Nothing is important. Not anymore.” He speaks to Alaric again at the bar, though he still seems suspicious of him. Sheriff Forbes comes to sit with Damon, hoping he'll be one of the bachelors in the Bachelor Auction. Later, he tells Elena that he'll be doing the auction, and, too drunk to do it himself, he asks her to button his shirt. He also say “she left you, she sucks” instead of listening to Elena's news about finding her birth mother. Stefan questions Damon again about Isobel, and this time Damon realizes that someone else must want to know. When Alaric mentions his dead wife, Damon realizes the connection between Stefan's questioning and decides to torment Alaric about it. Little does he know, the woman he killed was Elena's birth mother, and when she confronts him about it, he reacts with extreme surprise. Later, in the boarding house, Alaric demands to know what Damon did to his wife and where she is. When he attacks Damon, Damon stabs him, killing him. He sits on the couch by the body until Stefan arrives, at which point he claims self-defense and leaves.
In There Goes the Neighborhood, Damon is visited in his home by Anna and her mother, Pearl. Realizing she's stronger than him, he sits down and listens to her. She reveals that some of the twenty-five vampires in the tomb are living with them in a farmhouse just outside of town. She also knows about the Town Council and wants a list of their names. She wants their supply of Vervain to stop as well. It's Pearl's plan to re-take Mystic Falls, and to get him to help her, she offers him Katherine's location. He says that he doesn’t want to see Katherine, but to further convince him, she pushes both of his eyes in, threatening his life. He later meets Kelly Donovan, the mother of Matt Donovan and Vicki Donovan at the Mystic Grill, soon joined by Jenna. The three of them sit down and start drinking. Jenna leaves when Damon and Kelly begin flirting more heavily, and somehow the two of them end up at the Salvatore Boarding House, where Stefan, Elena, Matt, and Caroline happen to be on a double-date. The kids see them making out, which ruins their night. Stefan and Damon remain at the house and are soon attacked by Frederick and Bethanne, two tomb vampires. Stefan manages to kill Bethanne, which sends Frederick running.
In Let The Right One In, Damon is at the boarding house, where Damon, Stefan, and Elena are discussing what to do about the tomb vampires. Damon storms out after Elena calls him a “self-serving psychopath with no redeeming qualities.” When Stefan later goes missing, Damon appears at Elena’s house worried that neither of them have heard from the younger Salvatore. He and Elena drive out to the farmhouse, where Damon demands Frederick let his brother go. He's unable to enter the house because of a human resident.
She has been compelled to never invite Damon into the house. When he comes back to the car, he and Elena meet in the rain; Elena wants to go in on her own, but Damon stops her out of concern for her safety. The two of them go to Alaric, and Damon lies to Alaric by insinuating that Pearl would know something about Isobel because of her connection to Katherine. Damon continually refuses Elena's attempts to help them, eventually allowing her to drive the ‘get-away car.’ During the mission to save his brother, Damon manages to kill several vampires without being badly injured, and when Elena and Stefan leave together, he and Alaric remain behind to face the tomb vampires. Pearl comes back before they're attacked, admitting that she had no idea Stefan was being tortured, and that it shouldn't have happened. He's at the bar at the end of the episode, admitting to Alaric that he lied about Isobel. Alaric punched him and left the bar, but Damon seemed rather unaffected. Damon comes home to find Stefan devouring as many blood-bags as possible.
In Under Control, Damon tries to coax Stefan to drink human blood to get his strength back. He even leaves his glass full of blood behind and sarcastically runs back to get it, smirking. Damon is later seen attending a Town Council meeting, where he first encounters Elena’s uncle, John Gilbert. After she begins fearing Stefan is out of control, Elena invites Damon over and asks him how long Stefan will be this way. While perusing her room, Damon tells her that John is in the town council, also suggesting that since Stefan was ‘under control’ so long, the Damon-like monster inside was fighting its way out.
At the Founder's Day Kick-Off Party, Damon taunts Stefan about drinking to stop the blood cravings. Damon later compliments Sheriff Forbes, who he calls ‘Liz’ in a friendly way. She tells him that they might have more vampires in town, because what John Gilbert said about blood-banks being robbed was completely true. Damon seems suspicious when Jeremy asks about Vicki Donovan. When they encounter one another at the bar, Elena asks if Damon knows what his brother's been up to, and he says he's been too preoccupied with hers, expressing concern that Jeremy is asking so many questions. When John Gilbert and Damon talk outside of the party, John reveals that he knows what Damon is, and Damon responds by snapping his neck and pushing him from the balcony. Damon later reports to Stefan that he killed Elena's uncle. Damon later sees John Gilbert standing to give a speech, and he expresses shock and, to Alaric, points out that John is wearing the same ring. They talk again later (with Alaric present), and John reveals that he knows Katherine and he knew Isobel; that he gave Alaric’s ring to Isobel in the first place. At the end of the episode, Damon leaves another glass of human blood in Stefan's presence, but this time Stefan drinks it.
In Miss Mystic Falls, Damon is visited by John Gilbert and Sheriff Forbes. John suggests that he and Damon work together to track down whoever is stealing from the blood banks. Anna comes to visit him later, and though he warns her about the Founder's Council being onto the tomb vampires, she says she hasn't been to the blood bank in at least a week, and the other vampires are gone. Damon goes home and confronts Stefan for being the thief, though he seems elated by Stefan’s new diet. He also finds Stefan's fridge of human blood.
John Gilbert comes back to the Salvatore Boarding House to tell Damon that he wants the Gilbert Device. He wants Damon to get it from Pearl, who was ‘friendly’ with Johnathan Gilbert back in 1864. He rejects the idea of helping John, but when he sees Anna again at the Miss Mystic Falls Pageant, he inquires about the device. Later, he comes to the changing room upstairs and tells Elena about Stefan’s fridge full of blood. When Stefan vanishes before the dance begins, Damon steps in to escort Elena onto the dance-floor. When the dance is over, Elena pulls Damon aside and they realize one of the contestants is missing. They search for him in the woods, only to find him feeding on Amber Bradley. Bonnie arrives and manages to subdue Stefan, but, in his right mind again, Stefan flees. Later, Pearl brings Damon the device she stole from Johnathan Gilbert as a peace-offering because Anna wants to stay in Mystic Falls. After Elena tranquilizes Stefan, Damon carries him to the dungeon and locks him inside, and the two of them sit in the hallway together.
In Blood Brothers, as Elena and Damon take turns ‘baby-sitting’ Stefan at the boarding house. The two brothers slowly let Elena in on their history, how they both became vampires. Damon completes the story by telling her that Stefan forced him to feed on a human. Damon also taunts Elena by telling her that Stefan prefers golden retriever puppy blood. Damon and Alaric also go on a quest for information about Isobel, where they encounter one of the tomb vampires, Henry. The vampire reveals that John Gilbert has been working with him to keep an eye on the other tomb vampires. They end up killing him and having a moderately deep conversation about searching for their ex-lovers. Damon returns to Elena, where he concludes the story of their vampiric origin. Stefan later approaches Damon while he’s drinking in the living room, and Damon tells him to stop feeling his guilt. He then says that he hated him for all those years not because he forced him to turn, but “because she turned you.” Damon thought Katherine’s love was only for him.
In Isobel, Damon expresses distaste for Stefan’s new ‘cured’ personality while on the phone with Elena. He also seems concerned by Elena meeting Isobel for the first time. While they’re meeting, Damon is pacing beside Alaric just outside the Grill. Damon explains that Isobel has a ‘switch’ she can use to turn off her emotions, though he denies that he has humanity himself. Isobel later finds Damon in her temporary home, playing a game of cards involving stripping. She attempts to threaten him, but Damon continues questioning her about the Gilbert Device. When she kisses him, Damon pins her to the ground and threatens to ‘rip her to bits’ for what she said to Elena. He told her to tell Katherine to come get the device herself. Later, Elena tries to get the device from Damon so Bonnie can de-spell it; Elena hopes to trade the device for Jeremy, who has been kidnapped by Isobel. Bonnie displays her powers by retrieving Damon's favorite book, Call of the Wild, from the library shelf with only the power of her mind. He admits that he doesn’t trust Bonnie, but he will trust Elena, so he gives her the device. Damon is also present for the ‘de-spell.’ When they make the trade with Isobel, Damon and Stefan are present. Elena asks Isobel how she knew Damon would give her the device, and Isobel responds, “Because he’s in love with you.” After the exchange, he is standing in the same spot, silently watching Stefan and Elena hug. Stefan later confronts Damon about it, but he seems to be alright with his love for Elena, because it means he’ll protect her. Damon also reveals that John Gilbert is Elena's real father, and he's amused that the others didn’t put the pieces together as quickly.
In Founder's Day, Damon is shocked when Elena arrives looking just like Katherine. When she and Stefan are on the parade float waving to the crowd, Elena waves, smiling at Bonnie, and Damon appears between them and waves back. He then turns to Bonnie and thanks her for de-spelling the device, surprising Bonnie with his sincerity. He sees Elena at the Mystic Grill later and tells her that he likes her better in normal clothing. She says that Stefan is worried about their ‘friendship.’ When Damon overhears her attempting to apologize to Jeremy, he's angered by Jeremy's response and follows him outside; he tells him to give his sister a break. Stefan ‘rescues’ Jeremy from him and insists Damon is only doing it for his own benefit. While wandering around during the Founder's Day Celebration, Damon encounters Anna, who tells him the tomb vampires will be killing the founding families as soon as the fireworks start. Damon goes straight to Alaric, and then to Elena and Stefan, who he warns to leave the party as soon as possible. He goes to the building where John Gilbert is setting up the device, but, unfortunately, Bonnie never de-spelled it, and it made him collapse. He was injected with Vervain and put in the basement of the Gilbert Building to be burned alive. Stefan, with the help of Bonnie, manages to save Damon’s life. After being rescued, Damon visits Jeremy to tell him about Anna's death. He offers to wipe Jeremy's memory again, but Jeremy tells him he still feels ‘empty’ inside, and forgetting will fix nothing. He also admits that what he did to Vicki Donovan was wrong and apologizes for his part in it. When asked if vampires can shut out their humanity, Damon told him the truth, not realizing that Jeremy was going to kill himself. While leaving, Damon encountered who he thought was Elena on the porch. He thanked her for seeing something in him worth saving, and after kissing her on the forehead, he kissed her on the lips, only to be interrupted by a very confused Jenna. It turns out this was not Elena, but Katherine pretending to be her.
In The Return, Directly following the events of the season one finale, Damon arrives at the hospital, expressing worry to Sheriff Forbes about her daughter, Caroline. She tells him that the mayor, Richard Lockwood, is dead, but that he couldn’t have been a vampire. He comforts her, but seems incredibly intrigued by the fact that Lockwood was affected by the Gilbert Device. When Elena arrives at the hospital worried about Caroline. He points out that Bonnie doesn’t know how to cure Caroline with a spell, and offers to give Caroline enough blood to make sure she lives. Elena turns it down immediately, but Bonnie agrees. When Bonnie leaves, Damon attempts to bring up the fact that they kissed, but Elena blows him off, saying she has no idea what he's talking about. He grabs her arm, saying, “If you wanna forget this happened, fine, but I can't.” Jenna arrives at that moment, telling Elena something that Elena claims was never said. This is when Damon first realizes that Katherine Pierce is in Mystic Falls impersonating Elena. He recruits Elena and heads back to her home, where they find Stefan, who had just got out of a fight with Katherine. The three of them sit down in the dining room and talk about what Katherine wants, where Stefan asks Damon exactly what happened between them. Damon admits he kissed her, thinking she was Elena, and Stefan attempts to attack him. Elena stops him, claiming that she wouldn't do that. While trying to formulate a plan, Damon leaves, declaring that he'll just ignore her and see where that gets him. Damon goes to the Lockwood Mansion and breaks up a fight between Carol Lockwood and Elizabeth Forbes, who are discussing the death of the mayor. He questions Sheriff Forbes about Mason Lockwood and finds out that he's Tyler Lockwood's uncle, and the brother of the mayor, but he knows nothing about the Town Council. When Bonnie goes to talk to Damon in the dining room, wondering if he's suspicious about both Tyler and the mayor being affected by the Gilbert Device, he ends up irritating her until she uses magic to hurt his head. He later speaks to Elena out on the Lockwood's porch, where she asks him how he's doing. He doesn't admit that he's hurt until Elena tells him that she's surprised he thought she'd kiss him back. He also appears after Katherine stabs Stefan, trying to pick a fight with his little brother, though he doesn’t seem too serious about it. Stefan warns him that Katherine will get between them, but Damon, sarcastically, denies that it's possible.
That night, Damon encounters Katherine in the Salvatore Boarding House, where the two share a heated kiss. He stops them before they have sex, asking extremely modestly if she'll just tell him the truth. She tells him that she's never loved him, which literally rockets him off the deep end. He shows up at Elena's house drunk and angry, demanding that Elena admit she has feelings for him. He forces her to kiss him, but when she denies him with the same line Katherine used, “It's always gonna be Stefan,” he seems momentarily emotionally broken. Jeremy interrupts, and Damon pins him to the wall and snaps his neck. While Elena falls to her brother’s lifeless body, Damon steps further into the background, appearing to, in some capacity, realize the magnitude of what he's done. As The Return draws to an end and Elena declares her hatred for Damon, he's seen hurling a glass into the fireplace, his face contorted with anger.
In Brave New World, Damon is first seen having tea with Carol Lockwood. She asks Damon to spearhead the Town Council while she's acting as interim-mayor. He accepts just as Mason and Tyler come back to the house, and listens to their conversation about anger problems. When Stefan comes home later, he seems to have occupied himself with investigating the Lockwoods' family secret. He later attends the Carnival, where he speaks to Jeremy. When Jeremy threatens to tell everyone about vampires, Damon grows serious and drags him behind the concession stand, where he takes his ring and puts him in a headlock, pointing out how easy it would be to really kill him. He also watches Mason and Tyler arm-wrestling, where he volunteers Stefan to go up against Mason. Stefan admits that he's supernaturally strong after losing to him, which further interest Damon. He compels a carnival worker to pick a fight with Tyler to make him angry. Later, the newly-transitioned Caroline confronts Damon in the school hallway, telling him that she remembers everything he compelled her to forget. He goes straight to Elena, and, along with Stefan, they meet in Alaric's classroom. He is convinced that killing Caroline is the only thing they can do, and, locating her by the dead body of her newest victim, he attempts to stake her. He's stopped by Stefan the first time and Elena the second, who bravely steps between him and Caroline. He’s in charge of disposing of the body, and when he says something particularly crude in the presence of Bonnie, she sets him on fire. Elena manages to stop the witch before Damon is killed. When Damon returns to the boarding house, Jeremy is there, and he's laced Damon's alcohol with Vervain. He admits that he was there to kill him, but decided against it because of the blind hatred of his parents.
In Bad Moon Rising, Damon is first seen in the Salvatore Boarding House talking to Alaric, Stefan, and Elena, discussing if it's possible for Mason Lockwood and Tyler Lockwood to be werewolves. They decide to go to Duke University, where Alaric's wife, Isobel, still has an office full of research. Stefan doesn’t come, as he’s still watching over Caroline, and when Damon taunts him for this, Elena kisses Stefan to spite him. Throughout the drive, Damon tries to convince Elena that he knew Jeremy would come back to life when he killed him. When they arrive on campus, Isobel's old research assistant lets them into her office, but attempts to shoot Elena with a crossbow, as she knows who Katherine is. Damon moves in front of her, taking the arrow in the back, and Elena is the one to pull it out. Alaric discovers a book describing ‘The sun and the moon curse.’ She tells them that werewolves are hard-wired to hunt vampires, and that a werewolf bite is fatal to vampires. Disturbed by this, Elena calls Stefan to warn him.
Also, she asks Isobel's research assistant what she knows about Doppelgängers, which seems to interest Damon. He taunts her again with the information he claims to know. When Elena tells him that friends are supposed to help each other, he follows her to the car and gives her a book, which bears Katherine's original last name. He admits that he doesn't want to lose their friendship forever. Near the end of the episode, he walks her to her door, where she asks him if he honestly knew Jeremy was wearing the Gilbert Ring. He genuinely apologizes, but Elena tells him that he’s lost her forever, revealing that she manipulated him to get information about Katherine. Hurt, Damon tells her that she has much more in common with Katherine than her looks.
In Memory Lane, Damon appears in the Mystic Grill to taunt Elena about a party he'll be attending at the Gilbert House. He wants to find out more about Mason Lockwood, and throughout the evening, he continues to drop innuendos to Tyler's uncle, like drawing a wolf while playing Pictionary, and trying to get him to serve the pie with a silver utensil. Mason confronts him in the kitchen, hoping to keep the age-old rivalry out of their lives. Damon continues to antagonize him, suspicious about his presence in Mystic Falls. Eventually, he agrees to a truce, but he takes a knife from Jenna's silver set and follows Mason outside, where he stabs him in the stomach. Mason heals immediately, warning Damon that he’s made an enemy. After Elena and Stefan have their fake fight at the grill, Damon leaves and encounters Katherine outside, who he reacts to coldly.
In Kill or Be Killed, Damon continues to listen in on Stefan and Elena’s fake arguments, revealing that he knows it wasn't real. He takes a cup of lemonade from a little girl, but is shocked to learn that it's been spike with Vervain. It was part of a plan executed by Mason Lockwood to show Elizabeth Forbes that Damon was a vampire. Furious, Damon attempts to kill Mason, but he and Stefan are shot with wooden bullets in the forest, falling right into Elizabeth’s trap. She takes them to The Lockwood Cellar, where she demands to know how he can walk in the sun. Damon doesn’t tell her, but says that he thought they were actually friends. She shoots him repeatedly with wooden bullets until, eventually, Caroline manages to save their lives. Damon feeds on one of the dead deputies and tries to convince Stefan to do the same. And then, staggering because of his injuries, he confronts Sheriff Forbes, who asks him to kill her. Damon refuses on the basis that they're friends, keeping her locked up until the Vervain leaves her system so he can compel her to forget that he, Stefan, and Caroline are vampires. Later, when he encounters Elena in the living room of the Salvatore house, she tells him that sparing Caroline's mother was more like the Damon that she was friends with.
In Plan B, Damon is visited by Jeremy Gilbert, who tells him that Mason Lockwood is looking for the moon stone. Alaric comes by later, surprised to see Jeremy. He gives Damon the research from Isobel's office. Damon wants Jeremy to retrieve the moon stone from Tyler, and, upon finding out that Katherine and Mason are together, he speculates that Katherine wants the moon stone. The brothers ask Bonnie to touch Mason Lockwood to find out what he wants with the stone. He also asks what's happening when she ‘ju-jus’ his brain, suggesting they do it to Mason or Katherine. Though he asks rudely, Bonnie agrees to help them. She uses her magic on Mason, effectively subduing him so that they can capture him. Damon takes him to the Salvatore Mansion and chains him into a chair. While there, Bonnie attempts to get into Mason’s mind, revealing that the moon stone is being kept in a well of some kind. When Mason grabs her, Damon pries his hand away, thanking her as she's leaving the room.
He cruelly tortures the young man by shoving a red-hot fire-poker into his chest repeatedly. He questions him about Katherine, but gets no response. Jeremy later delivers wolfs bane, which Damon uses to further his torture of Mason. He shoves the plant into Mason's mouth, causing him immense pain. Mason reveals that he's getting the stone for Katherine so she can lift the curse of the moon, because she supposedly loves him. Seemingly entertained, Damon tells Jeremy to leave or get over his sympathy. After Jeremy leaves, he ends Mason's life by ripping his heart from his chest. Stefan arrives later, while he's cleaning up the body, giving Damon the moon stone to hide. Finding that the last number Mason dialed was Katherine's, Damon calls her, much to Stefan's disapproval. He taunts Katherine with Mason's death, angering her. After Jenna stabs herself, on Katherine's compulsion, Damon confronts Elena and apologizes for provoking her.
In Masquerade, Damon participates in a conversation with Stefan and Caroline, claiming that he's going to the Masquerade Ball to kill Katherine. Bonnie comes over later, while Damon and Alaric are discussing weapons in the background. Stefan and Damon show up at the Masquerade Ball with masks on, discussing how one of them might hesitate while killing Katherine. They meet up again after Katherine kills Aimee Bradley; Stefan wants to call the plan off, as he didn’t anticipate human death, but Damon objects and they agree to go through with it. When they trap Katherine in one of the Lockwood Mansion's rooms, they attack her viciously, stabbing her multiple times with their supply of stakes.
Jeremy arrives to tell them that their every action toward Katherine is being reflected onto Elena, which stops the in their tracks. Katherine continually tries to hurt herself to cause Elena pain, but she’s stopped by the Salvatores. She tries to make a deal with them; she wants the moon stone back. She also tells Damon that he used to be boring, and tries to antagonize them by pointing out Damon's love for Elena. Damon is the first to give in to her taunts, attempting to stake Katherine after pouring her a drink. Stefan stops him, but Katherine continues to play with his emotions, wondering when Damon got so hot. The witch Lucy uses the moon stone to subdue Katherine, apologizing to the brothers for her involvement with Katherine. Damon carries Katherine’s body to the tomb, throwing both her and the moon stone inside. As he shuts the door, she tries to stop him by claiming that Elena is in danger. He listens to her momentarily, but then shuts her inside. Damon, again, seems to have been emotionally affected by Katherine as he walks away.
In Rose, Damon appears at Caroline's house, whose explaining how Tyler killed a girl at the Masquerade ball. He questions what Caroline has told Tyler about him and Stefan, convinced he knows something. He tells her not to befriend Tyler. Later, he talks to Stefan about Elena's disappearance. He tells him that Katherine knew Elena was in danger. The two of them take a Vervain grenade from Alaric and, using Bonnie's instructions, go to rescue Elena. Stefan thanks him for coming, but attempts to get him to admit he only came because he loves Elena.
Before they get to Trevor and Rose's hideout, the two of them share a blood-bag, where Damon taunts him with the darkness in his past, wondering if Elena would ever ‘open her veins’ to the old Stefan. The two have a brief conversation outside before coming in to rescue Elena from Elijah. Damon drives a large piece of wood through Elijah's chest, and while Elena is hugging Stefan, she mouths a thank-you to Damon, as well. Later, when Damon is drinking at the boarding house, Stefan approaches and tells Damon they should learn to work together, or they won't be able to protect Elena. He also apologizes for making Damon turn into a vampire. Damon seems surprised by his words, and this prompts him to visit Elena in her bedroom, where he reveals that he found Elena's necklace. He doesn’t give it to her at first, holding it as he tells her that he loves her, but that he doesn’t deserve her; Stefan does. Tears can be seen in his eyes as he says this. He compels her to forget what he said and, after returning the necklace, leaves her room.
In Katerina, Damon expresses immediate distrust toward Rose, who comes back to tell them that a legendary vampire named Klaus is after Elena. He doesn’t want Elena to believe that she's in danger. After Elena leaves to talk to Katherine, Damon spends the day with Rose. He asks her if she knows where Klaus is, and convinces her to take him to see the vampire who supposedly knows where to look. When they meet up with Slater at a vampire-friendly café, he threatens her against tricking him, but she proves that she's much stronger than him by turning the tables. She tells him that he can trust her, and the two of them go inside. Slater immediately recognizes Damon; he knows the year he was turned and the person who turned him, which seems to make Damon suspicious. They talk about Slater’s very long link to Elijah, which was severed when Damon killed him. Slater tells them that, if Elijah wanted the moon stone, he might've been planning to break the vampire-side of the curse so that the werewolves wouldn't break their side.
Damon wonders how to break the curse, but they're interrupted by an attack from Elijah, who breaks the windows of the café. Rose is seriously injured by sun exposure and Damon is forced to carry her back to the car, where she tells him that they're all going to be killed by Klaus. Later, Rose apologizes for the surprise attack, expressing a desire to save Elena. She tells him to turn the ‘switch’ off of his emotions, and the two of them have sex. They're seen sitting by the fire in their underclothes, where Rose points out that having a ‘switch’ is a lie, and that they can’t actually shut off their emotions. Rose gets a call from Slater, who tells her she needs the moonstone to lift the curse, and a witch to figure the rest out.
In The Sacrifice, Stefan and Damon visit Katherine together, as the moon stone is in the tomb with her. They come directly to Elena's home afterwards, explaining that she wanted out of the tomb, if they wanted the moon stone. They also tell her that they must "release" the spell from the moon stone so Klaus won’t be able to sacrifice Elena. When Elena tells them that she doesn’t want Klaus to kill everyone she cares about, both brothers express extreme surprise. Damon appears later during their meeting with Bonnie, where Jeremy tries to convince them to let him retrieve the moon stone. While he's planning to incapacitate Katherine to get the stone, Damon gets a call from Rose, who tells them about Elena's plan to give herself over to Klaus.
She tells him that she would rather die than let Klaus kill the people she loves. He threatens her, grabbing her arm, and when she attempts to hit him, he menacingly warns her to never do that again. Three men arrive and Damon immediately tries to protect Elena, even from Elijah, who was supposed to be dead. Elijah flees, leaving Damon to drive Elena home on his own. The two of them bicker on the front porch, but Elena is surprised to find an injured Jeremy waiting for her. When she finds that Stefan has been trapped in the tomb with Katherine, Damon stops her from entering, restraining her against the doorway until she leaves. Stefan makes him promise to protect Elena while he’s unable to.
In By the Light of the Moon, Damon visits Stefan in the tomb to tell him that they trapped Elena in her own house. He tries to give him blood, but Stefan refuses, not wanting to share with Katherine. He comes to Elena’s house later to be one of her ‘babysitters,’ taunting her about not being able to leave. She’s angry with him, but Damon continues to have a care-free attitude. He gets a call from Alaric, who tells him that a woman from Florida has come searching for Mason Lockwood. He meets Alaric at the bar, who's been having a conversation with the woman.
While Damon is distracting her, Alaric pours wolfsbane into her drink. Damon talks to her about Mason, claiming to be one of his friends, but she responds suspiciously when he tries to get her to have a drink with him (in other words, to sip the wolfsbane so he can tell if she's a werewolf.) She doesn't fall for it, able to smell the wolfsbane in his drink. Damon threatens her, but she responds by declaring how strong she is on this night in-particular (the full moon). Alaric warns Damon to go home and stay inside, because one bite from the werewolf will effectively end his life. He goes home, where Rose has been waiting. He acts coldly toward her as she tries to apologize about helping Elena, admitting she has nowhere else to go. When Jules, the werewolf he taunted in the bar, leaps through one of the Salvatore's windows, she bites Rose's shoulder before Damon stabs her, getting her to run off. The bite heals immediately, mystifying both vampires. Rose is terrified that her life almost ended, and Damon comforts her with a hug. The two are seen again in the living room, where they begin another heated sexual encounter, but they're interrupted when Damon discovers that the bite on her shoulder has resurfaced. This is particularly devastating news to Damon, because the two of them were just beginning to develop a friendship.
In The Descent, Damon cares for Rose trying to convince her that she'll get better. When he looks at the worsening wound, he pretends that it’s getting better. He asks Elena to watch over Rose, but he rejects the fact that he's upset about Rose's impending death. Damon goes from there to the Mystic Grill, where he immediately goes for Jules. Stefan stops him, but he continues, sitting down at her table. Though he pretended he didn’t care about Rose, he asks how to cure a werewolf bite. She won’t tell him, and she taunts him about how much pain Rose will be in, and how she'll soon be rabid from dementia. He tracks Rose down after she slaughters a man. He meets up with Elena, who he arms with a wooden stake. He stops Rose before she takes yet another victim, pinning her to the ground in a parking lot. He comforts her when she realizes what she's done, picking her up and carrying her back to the Salvatore Boarding House. Damon watches over her after putting her back in his bed, where he reacts coldly to Elena's presence. He also snaps at Rose, denying that he cares about her. When Rose tells Elena that what it was like to be human ‘haunts her,’ he turns to watch, surprised when she begins writhing in agony.
He sends Elena away, getting into bed with Rose and holding her against his chest. He sends her a dream of the place she was born and raised, where the two of them sit together in a beautiful meadow. Just as she admits that she's no longer afraid of dying, actually hopeful she’ll see Trevor again, Damon stakes her to end her suffering. A tear goes down his cheek as he does this. He delivers her body to Sheriff Forbes to explain the earlier attacks on humans and when he returns to the boarding house, Elena is waiting. She tries to comfort him, but he denies that there's anything wrong with him. He responds angrily, saying that he feels emotions, and that ‘it sucks.’ He feels guilty because Jules was coming after him, not Rose. Elena hugs him anyway, and Damon's eyes begin to visibly water. That same night, Damon is lying in the middle of the road when a woman named Jessica stops her car to check on him. He tells her that he's lost (existentially, metaphorically). When he drinks alcohol from a flask, she runs back to her car, but he compels her not to move. He admits that he can't be what other people want him to be, and he tells her that he misses being human more than anything in the world, debating whether or not he should kill her. After he tells her she's free to go, he pursues her and kills her anyway.
In Daddy Issues, Damon first appears in the shower, a very dark look on his face as he listens to a news report about the people Rose killed. They mention the woman he killed in the road. He's angry with Stefan when Stefan brings John Gilbert back to Mystic Falls in an effort to save Elena. When Stefan tries to comfort him about Rose’s death, Damon reacts sarcastically and leaves. He goes to the Gilbert House, where he demands to know John's location. They share a distrust for John, where he says ‘I'm the good guy now, remember?’ Elena decides to go with him to find John out of concern that Damon will harm him. They find John at the grill, where he’s interrupting Jenna's date with Alaric. He tries to get information out of him, threatening his life because he's lacking his resurrection ring. His threat is ineffective because John doesn’t trust him. When Jenna tries to get him to date her friend, Andie Star, he blows her off. Elena receives a call from Stefan regarding Tyler Lockwood, and Elena and Damon have a heated discussion in the bathroom. He wants to kill Tyler because of what he knows. Elena tells him to be the better man. When John arrives, wondering what's happening, Damon tells John to keep Elena there so he can go rescue Caroline, who is being held captive and tortured by Jules and her boyfriend, Brady. Stefan and Damon are almost killed during this rescue, but they're spared by the warlock Jonas Martin, who was working with Elijah. John later gives Damon a bottle of white oak ashes and a silver dagger with which to kill an Original.
That night, Damon invites Andie Star to his house and the two of them share a bubble bath. Damon tells her that he's in love with a woman he can never have, and that he doesn't trust himself around anyone. He says that he kills people, but he compels her to be unafraid. When asked why he kills people, Damon says that he likes it, and that Elena wants him to be the better man, but his nature won’t allow it. While kissing her, Damon slips down her neck and bites her, filling the bathtub with her blood.
In Crying Wolf, Damon has bandaged Andie's neck, and they walk downstairs together. She reveals that she’s going to the Historical Society Tea Party, something Damon invites himself to. He also gets her story straight so she won’t tell anyone he bit her, and he tells Alaric, who has just come in, that she's his new girlfriend. He tells Alaric about the dagger, and Alaric says that he and Jenna will also be at the party. He claims his goal isn’t killing Elijah, but meeting him for the first time. At the party, which is being held in the large Lockwood Mansion, Damon meets up with Andie, also greeting Carol Lockwood and introducing himself, officially, to Elijah. Damon and Elijah have a conversation in the sitting room, where Damon questions his motives and goes so far as to physically block him from the exit. Elijah responds with physical violence, stabbing Damon in the neck with a broken pencil.
Damon returns to the Salvatore home, where he and Alaric are talking about how difficult it will be to kill Elijah. After Alaric leaves, Damon finds that someone has stabbed him in the stomach with a stake, and that same person leaps onto Damon’s back and injects him with Vervain. Jules is behind the attack. She chains him to a chair, which is ironically similar to the way he tortured Mason Lockwood to death, and questions him about the moon stone. Elijah shows up and kills four werewolves, saving Damon's life for the third time. Later, while on the phone with Bonnie, he’s told that Elijah and Elena's deal called for Elena's death. He calls Stefan and relays this information.
In The Dinner Party, Damon acts on his plans to kill Elijah. He's first seen on the phone with Stefan. He tells his brother that Tyler Lockwood has left town, leaving them with only one problem: Elijah. He reveals that he's going to be careful when killing Elijah. He speaks with Alaric, who expresses distaste with Damon and Andie's relationship. He invites Jenna and Elijah, who have been speaking of historic Mystic Falls, and Andie tells them they should have a dinner party. Damon jumps at the idea, and Elijah agrees. Damon goes to the tomb and, now that the spell is lifted and he can move around freely, he brings Katherine blood and clothing, wondering if what John Gilbert said about killing Elijah is true. Katherine tells him that if Elijah dies, she's stuck in the tomb forever, begging him not to kill the Original. By doing this, she confirms that it's possible to kill an Original. Damon denies (to Alaric) that he'll do anything to antagonize Elijah, but when Alaric leaves the room, he pulls the dagger and the ash from its hiding place. The party continues into a tense dinner, where Damon and John Gilbert, who arrived uninvited, prod Elijah for information. Meanwhile, Elena and Stefan figure out that if a vampire wields the dagger and kills an Original, it will die. Stefan calls Alaric and warns him, who is barely able to stop Damon in time. When they return to the dining room, Damon tries to convince Elijah to kill John Gilbert, and the two of them seem to put Elijah on the defensive. He threatens to take Elena away and protect her himself, so neither of them will see her again.
In the middle of this, Alaric uses the dagger to kill him, and the two of them lock him in the basement. Alaric is angry that Damon plotted Elijah’s death without him, and that he had to kill him with Jenna in the house. Stefan calls again to tell Damon that removing the dagger will bring Elijah back to life, and, panicking, Damon runs down to the basement. He finds it empty. Knowing that Elijah will come after Elena, Damon participates in a plan to bring him down, helping Stefan transport the body back to the basement. He finds the moon stone in Elijah's pocket and decides to hold onto it. Elena then tells both Salvatores that she doesn't want to be kept in the dark anymore, if they truly want her to keep fighting. They agree, and Damon wonders how he changed her mind; when Lexi is mentioned, Damon recalls the first time he ever met her, and that he told her to take care of his brother. She warns him that his hatred will get the best of him, which is ironic, because it eventually consumed his life. At the very end of the episode, Damon enters his room and finds Katherine naked in his shower. She reveals that killing Elijah removed his compulsion over her, and that she was able to escape the tomb. She claims she wants to help him.
In The House Guest, Damon first appears as Elena is leaving the house. He attacks her and pushes her against the wall, believing she’s Katherine and inevitably revealing to both Elena and Stefan that Katherine has escaped the tomb. It turns out that the person Damon attacked was actually Katherine, and that when Stefan went back to his room to attack who he thought was her, he nearly choked Elena. Damon talks to her down in the basement, where Damon is using a blow-torch on Elijah's body. He wonders if she knew that using the dagger would kill him, and, angry, he points the blow-torch at her instead. She continues to try to convince him that she wants Klaus dead as badly as they do. She even told him that she didn't care if he died, as long as she got out of the tomb. Damon remains in the house with Katherine. He's trying to find out where the witches were massacred. She antagonizes him and he ends up pinning her to the piano seat, where she says she's glad he's not dead. She gives him sparse information about the location while also asking why he cares. Stefan appears and suggests they find the Witch Burial Ground. When Luka Martin enters the Salvatore house using his mind, it leads into a scene between Katherine and Damon in which she leans over his shoulder and points out how her old friend, Emily Bennett, was burned alive in the same place the other witches were. Stefan comes they speak as if they're at a loss, but use gestures to reveal information to each other so that Katherine won’t know anything. Katherine calls for Damon when she's attacked by Luka, and he pulls the stake from her stomach, using the blow-torch to burn Luka alive. He later brings Katherine a blood-bag, but stabs her after she takes it, revenge for not telling him that the dagger would take his life. She tells him that John Gilbert and Isobel want Damon and Stefan out of Elena's life. He knew that killing Elijah would get her out of the tomb, so he gave Katherine a choice: either she stay and help them with Klaus, or he would kill Stefan. Damon points out that John Gilbert still tried to kill him, and Katherine tells him that, since she could only save one of them, she chose Stefan. Damon tries to go to Elena's aid when Jonas Martin comes after her, but Katherine stops him, as she plans to step into Elena's place at the house and kill him. He later tells Elena that it was Katherine's idea in the first place. He hovers in the background as Elena and Katherine argue, where Katherine tries to convince them that she's not a threat. In his bedroom, Katherine jumps onto his bed in a very short dress. Damon wonders how everyone knew that Emily Bennett was a witch back in 1864. He finds that Katherine was the one to expose her, and she reveals that he knows where the witches were burned, because he would’ve been there. She tries to kiss him, but he pushes her off, telling her to find somewhere else to sleep. This strengthens his resistance to the power Katherine has over him.
In Know Thy Enemy, Damon and Stefan are rushing downstairs, discussing why Isobel would show up on Elena’s doorstep. Katherine tells them not to reveal her presence in Mystic Falls, because it would be easier to keep ‘swapping places’ with Elena if no one knew about her. Damon, Bonnie, and Jeremy go to Jonas Martin's apartment, where she tells Damon that if she can find the place where the witches were burned, she can harness their power. Damon’s also in the living room when Katherine asks them all about their plan, which they refuse to tell her. Damon, Jeremy, and Bonnie later go to the Witch Burial Ground, where a mansion stands. As soon as he enters, Damon finds that the spirits there are vicious toward vampires, and they temporarily disable his ring so the sun will burn him. He manages to get out before he's burned too badly. While Bonnie and Jeremy work inside the house, he hovers on the porch. When he tries to enter, the door slams shut of its own accord. Carol Lockwood and Sheriff Forbes call Damon when John Gilbert is ‘killed’ at a social gathering. He tells them that John will come back to life and carries John’s body back to his house. His hands are bloody, so he washes them, and after receiving a frantic call from Stefan, he finds that Katherine has taken the moon stone from the soap dish, where he ‘cleverly’ hid it. He finds the place where Katherine is most likely to be hiding, and he and Stefan find Isobel's bags inside. At this point, Katherine, Elena, and the moon stone have gone missing. After Elena is released and Isobel dies in the sunlight, Damon approaches with the deed to the house, which will make Elena the owner. When she signs it, the Salvatore Boarding House will be inaccessible to any vampires she doesn't allow inside. Damon and Stefan figure out that Bonnie is their "secret weapon," now that she’s harvested the power of the dead witches.
In The Last Dance, Elena signs the deed, giving her ownership of the house. Outside, Damon and Stefan talk about Klaus. Damon wonders if she's dead, though he seems rather disturbed by the idea. Once they're finished, Elena invites Stefan in immediately, but makes Damon promise to listen to her. After Klaus sends Elena a message telling her that he'll be at the dance, Damon invites Alaric to the house and tells him to put him down as a chaperone. He attacks Bonnie, trying to prove that she's not strong enough, but she blows him across the room, revealing that she can kill any vampire, no matter how strong. At the dance, Damon suggests that everyone blend into the party. He goes to talk to Alaric, unaware that he's actually Klaus. Elena wants to warn Caroline and Matt about Klaus, but Stefan decides to do it himself, calling Damon over to dance with Elena. Damon is lucid and comforts Elena while they dance, drawing a few giggles despite their serious situation. He later dances with Bonnie, as he heard her and Jeremy talking earlier. He wants to know if killing Klaus through magic will kill her, and he wonders if there’s any way to keep her alive. After Klaus reveals his identity, Damon sends Elena to find Stefan, grabbing Bonnie and making a plan with her to fake her death so Klaus will give up in his attempts to kill her. He returns when Elena is grieving over Bonnie’s lifeless body, coldly telling them he'll deal with it. When he gets back to the house, having dealt with the body, Elena accuses him of knowing what would happen, and she slaps him. He finally explains that it was all a plan to save her life and keep her as their secret weapon. He leaves her there, but Stefan follows, upset that he didn't tell him about the plan and that he put Elena through so much emotional pain. Damon calls it ‘collateral damage,’ assuring Stefan that, at the end of the day, he'll keep Elena alive regardless of the cost. This is brought up again when Elena visits him in his room. She tells him that she won't let Bonnie die for her and he responds in a similar way, telling her that he would let anyone die to keep her alive. Her life will always be his first choice.
In Klaus, Damon sees Andie off to work while Stefan searches for Elena. He follows Stefan to the basement, where they find that Elena has brought Elijah back to life. He’s convinced Elena will get herself killed, deciding to do something about it regardless of Stefan’s resolution to trust Elena. He and Andie go to Alaric's apartment, where Katherine is being held prisoner. Damon can't enter, due to the fact that Alaric is still alive and hasn't invited him in, so he talks to Katherine through the door, offering her a small vial of Vervain, which will protect her from Klaus' compulsion, in exchange for the answer to a question: he wants to know why she turned on them with Isobel. She admits that she knew they wouldn’t be able to kill Klaus, and, pointing out where that betrayal got her, Damon hands over the Vervain. He returns as Elena is trying to leave again and physically restrains her, antagonizing Stefan. Andie tries to comfort him as he drinks by the fire, but he sends her away, leading to Stefan's entrance. Stefan darkly thanks him for being in love with Elena, if only it means Elena is being protected. The two get physical when Stefan claims that he has one thing Damon will never have: Elena's respect. Elena appears with Elijah and stops them, explaining that Elijah knows a way to bring her back to life after she's sacrificed. Elijah only requests an apology, which Damon refuses to give. He leaves angry and encounters Andie, in only her bra and underwear, waiting in his room. She wants to comfort him, but his anger gets the best of him and he bites her. He shows remorse by gently telling her to leave again, before he accidentally kills her. He’s last seen sitting there with watering eyes and bloody lips, staring after her.
In The Last Day, Damon is lying in bed listening to Elena, Stefan, and Elijah talk about the sun and moon curse. He approaches after Elijah describes how powerful Klaus will be, wondering why they can't just kill him beforehand. He suggests that they go through with their original plan to let Bonnie kill him, channeling the power of the witches, but Elena objects because a spell that powerful would claim Bonnie's life. Damon replies sarcastically, saying he'll write her a good eulogy. When Elijah reveals that Klaus will truly have to kill Elena to complete the ritual, Damon becomes aggressive, rejecting that the Elixir will work and positive that Elena won’t survive this new plan. After leaving, drink in hand, he’s approached by Stefan, who would rather trust Elena’s choices. Damon rejects that idea, and when Elena later comes to his room to assure him that he won't lose her, he forces her to drink his blood as a more definitive way of making sure she'll come back to life – as a vampire. Stefan intervenes and the two have a violent fight, which ends in Damon stabbing his brother through the stomach with a large piece of wood. He leaves angry once again, speaking briefly to Elijah in the sitting room. Elijah tells him that vampire blood nullifies the Elixir, pointing out that Elena will never forgive him for what he's just done. Damon then goes to the grill, where he and Alaric are approached by Klaus. The Original warns him against protecting Elena, or doing anything ‘stupid,’ telling him that the ritual would be happening that very night. Being himself, Damon does just that, visiting Katherine in Alaric’s apartment to ascertain the location of the vampire and werewolf Klaus will be using as sacrifices. She unwillingly tells him to go to the tomb, where she says both Tyler Lockwood and Caroline Forbes are being held. He's nearly stopped by the warlock guarding the tomb, but assisted by Matt Donovan, who he subsequently knocks unconscious for turning a high-powered rifle on him. Damon receives a call from Stefan as they are fleeing through the woods; Elena has already been taken by Klaus. Then, to make matters worse, the full moon bears down on them and Tyler begins his transformation, putting both Damon and Caroline in great danger. Tyler tries to bite Caroline immediately but Damon blocks him, receiving a bite on his forearm, near the crook of his elbow.
Damon goes straight from there to Alaric's apartment, where Klaus has been staying. He boasts about what he’s done to keep Klaus from completing the ritual, but Klaus reveals that he has the werewolf Jules as a backup. Klaus then knocks Damon unconscious, and when Katherine wakes him up, he demands to know why Klaus didn’t use him in the sacrifice, instead of Jenna Sommers. Katherine tells him that Klaus said Damon was already as good as dead, questioning him about the bite on his arm. Damon admits that he was bitten by a werewolf, which both of them know means the death of a vampire.
In The Sun Also Rises, the ritual begins and Damon and Katherine are still in the apartment, examining the wound on his arm. Katherine seems upset that he'll die, but Damon reacts coldly because, again, she chose to save herself instead of Jenna. He returns to the Salvatore Boarding House, and he seems to be in pain from his bite, as his walk falters when he goes to answer the knock of John Gilbert. He tells Elena's father that Klaus has Elena, but that, since she has his blood in her system, she'll come back as a vampire. The two of them go to the Witch Burial Ground, where he has a heated conversation with Alaric. He still appears to be in pain, which concerns Alaric. He's present for the conversation about transferring John's life-force into Elena's body, though he seems to think it won’t work.
He impatiently waits for the spell to be complete. Bonnie and Damon head out, leaving Alaric in the house. As Bonnie goes through with her plan to kill the transitioning hybrid, Damon kills Greta Martin and retrieves Elena's lifeless body. He carries her back to the old witch house and sets her on the couch in the main room, waiting by her side. When Alaric asks about Jenna, he gives him a sad look and a genuine apology. As Elena comes back to life, Damon makes sure she’s not in transition, and he's extremely relieved that she's alright. After the ritual, Damon attends the funeral of Jenna Sommers and John Gilbert, where he tells Stefan about his werewolf bite. Stefan assures him that they'll find a cure, but Damon believes that he'll soon die. He doesn’t want Elena to know so she won't have another grave to mourn.
In As I Lay Dying, Damon goes to Elena's house to earnestly ask for her forgiveness, not because he wants it, but because he needs it. Unaware that he's dying, she asks for more time to consider forgiving him, and Damon agrees wholeheartedly. He returns home and, directly after pouring himself a drink, he removes his sunlight ring in front of the window, planning to let himself burn to death. Stefan stops him and locks him in the basement, where Damon begins coughing up blood. His condition deteriorates rapidly from that point. He starts hallucinating about his time with Katherine in 1864, and the choices she gave him while they were together, such as feeding from her. The wound on his arm is significantly larger by the time Alaric comes by to watch over him. Damon grabs Alaric’s neck with one hand, begging his old friend to kill him, but Alaric knocks him back and refuses.
As he lays on the ground, he whispers Elena's name. Later, Elizabeth Forbes shows up with her deputies, but inevitably sets Damon free. He wanders through the showing of “Gone with the Wind,” where he’s found and escorted to the Mystic Grill by Jeremy. The sheriff finds them here and tries to shoot Damon, but when Damon flees, Jeremy is shot instead. He goes back to the movie, wandering around behind the screen, and encounters Elena. His hallucinations have become more extreme, and he pictures himself feeding from Katherine's neck back in 1864, transferring that memory to Elena in the present. When he realizes that he's biting Elena, he stumbles back and collapses. She hits her knees beside him, holding him against her chest as she searches for someone to help them.
Elena takes Damon back to his room, where she watches over him. Damon worries that he’ll be dangerous like Rose, but Elena refuses to leave his side. She gets into bed with him and holds his head to her chest, where Damon talks about the bad decisions he's made. He tells Elena to apologize to his brother for him, admitting that he deserves to die, after everything he’s done. He apologizes to Elena again and tells her that he loves her, which brings tears to her eyes. He then tells her that she would've liked him better as a human, to which she responds she likes him now, the way he is. She kisses him just before Katherine arrives to deliver the cure, which she says Stefan paid for by giving himself over to Klaus. She tells Elena that it's alright to love both Salvatores, because she did. She leaves and Elena and Damon remain to contemplate what's going to happen to Stefan.
Elena arrives at the Salvatore Boarding House to tell Damon that Sheriff Forbes gave them another lead. In secret, Damon has a whole map of Stefan and Klaus movement, Damon is recording all the reports of animal attacks, tracking Stefan and Klaus' trail as he doesn't want to involve Elena.
Andie is able to get Damon the address of the last victim's family member, to where Alaric and Damon travel. As they, Alaric and Damon enter the house, they find blood splatters on the furniture and walls. Two female bodies are in a sitting position on the couch. Damon immediately recognizes that Stefan did it, by the way the bodies were ripped apart, then pieced back together. The duo find a trap door that leads to a basement where chains were kept, making them believe werewolves sometimes came there or the two girls were werewolves themselves. Afterwards, Damon sets fire to all the evidence of the remains of the two ripped apart girls.
As Elena is dressing for her birthday party, Damon arrives and gives her a present which is actually the necklace she had lost, saying Alaric found it in his apartment. He accompanies her downstairs, where they find a huge party going on. Appearing to be worried about Andie's whereabouts and her being late for the party, he travels to her workplace, finding Stefan there.
Stefan compels Andie to stand on top of a rig and stay there until he commands her to move. When he tells her it is alright to move, she falls towards the ground. Stefan attacks Damon and keeps him against the wall, keeping him from saving her. It was his message to Damon, telling him to let him go. When he gets back to the house, Elena confronts him about all the leads he was gathering, and he tells her to stop looking for Stefan, because he's gone and never coming back and also that the Stefan, Elena use to know isn't there anymore.
Elena is still headstrong on bringing Stefan back, determination-fueled as she believes he called her. Damon still doesn't want to help her, and burns the papers containing the data he's been collecting. After Elena ropes in the help of Alaric and headed off the mountains in search of Stefan, Alaric secretly contacts Damon and tells them where they are, as he doesn't want Elena there without being protected. Damon comes running up behind up Elena and pushes (throws) her into the lake, telling her that she should go home, but Elena convinces him otherwise.
They find Ray Sutton and bind him to a tree; unfortunately, being a hybrid, Ray starts to transform and Damon leads a rabid Ray away, where Stefan saves him. Damon appears in Elena's room, telling her that he will help her bring Stefan back, because even in his darkest place, he still wouldn't let him die. Damon doesn't want to compel her, he wants the time they spent together to be real and he also wants her to remember what she felt for Damon in Stefan's absence.
Katherine calls Damon with news that Stefan and Klaus are in Chicago. Damon informs Elena of it, and they drive to Chicago. They first go to visit Stefan's old apartment, where Damon shows Elena Stefan's list of killings. Damon then goes to Gloria's Bar, asking Gloria where Stefan is. Gloria proves a bit helpful, telling him that they will be back later that evening. Elena and he concoct a plan where she will be able to talk to Stefan and Damon will distract Klaus. As Elena talks to Stefan, Damon faces Klaus, almost being killed if Gloria hadn't saved him. Katherine again calls Damon, and he tells her she was right but unfortunately they couldn't get him back.
After Stefan broke up with Elena, Damon keeps an eye on her by helping her make chili for the Founders Party, to make sure she doesn't break down. Elizabeth later requests the help of Damon to compel her ex-husband Bill to leave town. Alaric later approaches Damon and tells him to take a beat, meaning to stay away from Elena. At the council's meeting, Elizabeth reports that there hasn't been any vampire attacks. Bill then enters, accusing them of being blind, baffling Damon how Bill could have resisted compulsion.
As Damon, Elena, and Alaric walk out of the Lockwood mansion arguing about the return of Bill and whether or not vervain should be added to the water supply, they believe now that Stefan's not there, Damon needs help to keep himself in check. Damon temporarily kills Alaric as he didn't let him past.
Damon later goes back to the mansion, where Bill is. They talk about how he could have resisted compulsion, and Damon then attacks Bill, feeding off of him. Caroline intervenes and feeds him some of her blood to heal him. Damon and Caroline fight, and she runs off with her father.
Elena enters and they argue about him being so reckless, and that she doesn't want him to be that way. Damon replies that he's not Stefan and not even like him. At the Salvatore boarding house, Damon waits until Alaric is revived, apologizing, but saying that he's fed up that everyone wants to change him. Katherine shows up at the front door with Elena's necklace, offering him to go on a road trip, to find a way to beat Klaus once and for all.
Damon and Katherine and driving away from Mystic Falls. Along the way, Katherine pities Elena for trying to change Damon, and tries to seduce him, only Damon resists. He stops the car, demanding to know what Katherine's plan is. She tells him that Klaus is searching for the necklace, and that means she has leverage. She shows him that she has Jeremy in the boot. Katherine reveals that Pearl had information on a vampire hunter that could kill the Originals. Pearl had shared all her information with Anna, but with them both dead, Jeremy is the only one able to contact her, which is why Katherine kidnapped him.
After Damon hurts Jeremy, Anna's ghost is quick to tell them her secrets, and give them a name: Mikael. Katherine had been keeping Damon's phone and Damon demands it back, where he finds out that Bonnie has been searching for him and Klaus is back in town. Damon goes back to town, having a face down with Klaus, scaring him away by telling him Mikael has been released. He then goes to save Elena, and takes her back to the boarding house, where he tells her he will never leave her again. Stefan interrupts them, informing them he will be staying there to keep an eye on Elena for Klaus' sake.
Damon finds out that Stefan is holding parties in the house where he is recklessly drinking from young girls if they loose a game of Twister. Rebekah enters, telling them that Klaus left her alone. She walks off to find herself a room, even after Stefan and Damon denied her the invitation of staying there. Damon calls Katherine to find out how far she is with waking Mikael, but unfortunately she has had no luck. Damon then calls Elena at school, telling Elena rather not to visit their house not only because of Rebekah, but because Stefan is wild.
Elena is training at Alaric's apartment, and Damon comes to give her a lesson on where a vampire's weak point is, and where she could stake one. Alaric, Damon, Elena, and Caroline devise a plan to capture Stefan and lock him up. Tyler disagrees with the plan, and Damon figures out that he's been sired and so is loyal to Klaus because his blood transformed him.
Damon distracts Rebekah with his charms, but she suspects that he has only been distracting her and trying to hide something from her. She stabs him with a piece of wood and walks away. Later, at the Salvatore boarding house, Damon is applying first aid to Elena's face after she almost got barbecued. They both talk about how they acted that night, and how they executed their plans. Damon is later knocked unconscious, and it is revealed to be Mason who attacked him.
Damon tied to a chair with a hit poker in his chest. Damon believes it to be Stefan that did it, but Mason had actually been the one who tortured him. Damon drives downtown to the set-up of the Night of Illumination, telling Bonnie that she screwed up with the spell, and that she needs to fix it, because Mason is after him for revenge. Alaric and Damon are at the bar when Mason appears, hitting Damon in the head with a glass. Mason tells him that he only wants an apology. Damon gives him an apology that he doesn't really mean and Mason accepts, telling him they should meet down at the old Lockwood cellar, where he will help him with the Klaus problem.
Damon goes to the cellar as he had hit a snag in his other lead to defeat Klaus. Damon breaks through a wall that reveals a tunnel, and the duo traverse through it. Unexpectedly, Damon is stabbed with wooden stakes from different directions. Mason goes to fetch a shovel to break the stakes apart, and then removes them.
Damon can't believe Mason trusts him after all he's done. Mason confesses that he's not after revenge, but redemption, and that he wants to help Tyler. They find a cave, but somehow Damon can't enter it, and Mason goes on ahead. When Bonnie does the spell to send the ghosts back, Mason disappears, and Damon is in need of a person to get into the cave. He calls Alaric, as he's the only person Damon trusts other than Elena who he doesn't want to place in danger. Damon repeats the same apology to Alaric, but meaning it this time.
He frees Stefan from his captivity in the cellar and goes to a bar with him. There they talk about brotherly bond and he helps to hide the fact that Stefan bites the barkeeper several times. They meet Mikael who says he will rip Damon's heart out if Stefan doesn't tell him where he can find Klaus. Then, he spares Damon after Stefan says he could lure Klaus back to Mystic Falls. Outside, Damon beats Stefan and goes away. At the Gilbert house he lies in Elena's bed and when she lies down as well, she states that Damon maybe will be the only one who can save Stefan.
He plans together with Mikael how Klaus can be killed. Mikael shows him the White Oak Stake, the only weapon that can kill an Original. When Stefan comes, Mikael feeds on him, incapacitating him. At the homecoming dance, he kills a hybrid and confronts Tyler after he injected Caroline with vervain. When Tyler almost bites him, Bonnie stops Damon from staking Tyler with the White Oak Stake. When Mikael and Klaus have a conversation he surprises Klaus after Mikael stabbed Katherine, who was impersonating Elena. He stabbed him in the stomach and was about to stake him in the heart when Stefan stopped him. Stefan is free and Damon gets home, angry. He tells Elena that he had Klaus and could have finished him off. He receives a phone call from Katherine, saying goodbye. Elena calms Damon down and they promise that they will survive life without Stefan.
Damon is with Alaric at the Grill, drinking. Elena approaches him, while he is playing darts. They have a conversation but Klaus interrupts them. Together with his hybrid, Tony, he has come to ask Damon and Elena to find Stefan. Later, Klaus comes to the Salvatore Boarding House and reveals that Stefan stole the coffins of the Originals. Damon was called to the Gilbert House after Klaus almost killed Jeremy and splits the news. Then he and Elena go to the Witch House, trying to find Stefan. While waiting outside because the witches don't want to let him in without burning his skin, Elena talks to Stefan unsuccessfully. Finally, he bares to go inside the house to talk to his brother.
Damon beats the truth out of Stefan by staking him in the stomach several times. Stefan reveals that he saved his brother because Klaus' hybrids would have killed Damon. After telling him to stop saving his life, Damon leaves. Later, Stefan reveals that the dead witches are hiding the coffins, making them invisible for Klaus. After he came to Elena's house, she gets Damon to compel Jeremy. Damon sits down and compels him to leave town to go to Denver. Outside, he and Elena discuss if it was right to compel Jeremy and they also talk Stefan. Damon thought he doesn't have to feel guilty anymore and is about to go. Then, however, he says he only has one thing to feel guilty about now and they share a passionate kiss.
Damon takes a shower and then teams up with Stefan to go to the Witch House because they are meeting Bonnie. They find out that a hybrid was there and Damon killed him by ripping his heart out. At the house he sums up that three Originals are in the coffins but there are four coffins. He goes with Alaric to a fundraising for the Wickery Bridge. As they talk about Elena and that there is something changing with her, Damon leaves and finds Klaus talking to Carol.
He has to find out that Klaus has convinced the mayor that his hybrids would protect Tyler and the town. After Stefan captured Elena and wanted her to turn into a vampire, he calls Damon, informing him. Then, Damon talks to Klaus that he has no idea if Stefan is really going to kill Elena and advises Klaus to obey. He picks up Elena after Klaus obeyed to get his hybrids out of Mystic Falls and takes her home. He hopes she will be okay and leaves. He went with Elizabeth and they find Brian, Meredith Fell's ex-boyfriend, staked although he's not a vampire.
He gives Bonnie and Elena the information about Abby. He later meets Alaric in the Grill and they talk about Meredith Fell and Damon hints that she could have killed her boyfriend. To talk to Meredith, he went to the hospital and accused her of having killed the medical examiner. When Damon was about to go, Meredith injected him with vervain to take his blood. He then wakes up and went to Alaric, telling him what his "girlfriend" has done.
Damon went to the Witch House, unaware of Klaus following him. He found out that the coffins were them and after the spirits stopped torturing him, Klaus got them to show him the coffins. After he figured out the fourth was gone, he threatens Damon that he will rip out his heart. After Klaus took the coffins, Damon went home and Stefan came in. They have a conversation where Damon asks how Elena is. As a response Stefan punched him, hard, because Elena told him she had kissed Damon. Damon states he doesn't want to talk about it. He then holds up a White Oak Ash Dagger which he has removed from Elijah's heart, bringing him back to life again.
Damon is with Stefan at the dinner hosted by Klaus. Before that, he had met up with Elijah, and they spoke. He helps Elijah remove the daggers from the Originals and bring them back to life. Then, he leaves and lets Elijah, Rebekah, Kol, and Finn take care of Klaus. After they leave the Originals, Damon and Stefan talk, and Damon thanks Stefan for saving his life all the time, and tells Stefan that he loves Elena.
Damon is with Stefan and Elena at the Gilbert house when discussing how Esther was in the coffin, and when Elena receives her invitation Damon does not want her to go because it is dangerous. Damon is at the ball talking to Carol when Elena shows up. He tells Elena she is not supposed to be there but then offers his arm, along with Stefan, to Elena as they accompany her to the Mikaelsons' ball. He tries to protect Elena from the Original Witch, Esther, saying that it is to dangerous to go and he won't let her. Damon then offers his hand to Elena with Stefan looking on as they go and dance together. Damon tells Elena that she looks stunning.
When it is time to switch partners, Damon ends up dancing with Rebekah. Damon is then shown walking into a room where Stefan is informing Elena he got her text, but he has his neck broken by Stefan who respects Elena's decision to meet Esther. When he wakes up, he is angry at Stefan but then understands Elena's decision but he then implies to Stefan that he cares too much and is not happy about the revelation. Damon finds Elena and tells her they are going home but Elena refuses. Damon says he is just trying to protect her and tells her that he is mad because he loves her. Elena then says that his love is a problem and Damon is severely hurt. When Kol tries to kill Matt, Damon, who is now unstable and angry, saves Matt and throws Kol from the balcony and breaks his neck. Damon, who is now drunk, goes up to Rebekah and they talk a little and after some persuading, they sleep together.
Damon is in bed beside Rebekah. When Damon and Rebekah go to the door, Elena is standing there looking shocked. Damon turns Bonnie's mother in to a vampire in order to break the witch bond with Esther. Later, it is revealed that Stefan lost the coin toss and should been the one to turn Abby into a vampire.
Damon spends some time with his brother in the time after that. He is worried because Stefan refuses to drink blood. Damon wants to help Stefan learn moderation and teach him how to control his bloodlust instead of being controlled by it. Damon promises whenever Stefan would go too far, he would pull him back. When Stefan asks why he would do this, Damon confesses to Stefan that he is all that he has left.
Damon enlists Sage's help to get into Rebekah's mind and see what she is hiding. He ends up sleeping with Rebekah, and through Sage's special ability to get into people's minds, she discovers that White Oak tree from the Old World which potentially could kill the Originals is not totally burned down.
Damon then looks through old records from his bookshelf, and discovers that the White Oak was used to make Wickery Bridge. He then goes to Wickery Bridge to retrieve the Oak, only to be disappointed as Rebekah is burning it. Damon reveals to Stefan he sold his rage to Sage after she crossed him by telling Rebekah about the White Oak, and that Rebekah left out a part of the bridge made of the same white oak: the Wickery Bridge sign.
Damon meets Elena at the door and refuses to let her in. He assures her that the history teacher is okay. She suspects he is up to something but eventually takes his word for it. Alaric, Stefan, and Damon have spent the night turning the old Wickery Bridge sign into white oak stakes. Apparently, Rebekah's more than a bit annoyed at Damon for seducing her and then using Sage to read her mind so she sneaks into the Salvatore boarding house and knocks Alaric out.
Before Damon can figure out what's happening, Rebekah's within kissing distance. She greets him as her lover. She then stabs Damon in the gut. Damon dreams that Elena has come to save him. When he wakes, he realizes that Rebekah planted the dream in his mind. Once he finds out about the bloodline issue, Stefan marches over to Klaus. He drops a bag filled with eight of the remaining daggers on the floor, tells them Finn is dead, and offers to trade the weapons for Damon. It sounds too easy but Klaus compels a nearly drained Damon to go home. Before Damon amputates his own hands in an attempt to free himself from the chains, Klaus tells Damon to stop. Then, he compels Damon to tell him how many stakes really exist and Damon tells him the truth that there are eleven.
This prompts Klaus to make a big speech about how he gave Stefan's life purpose by giving him something to hate. He's so full of himself that Stefan can't help but try to kill him. Klaus easily squashes his attempt. Then, Rebekah frees Damon and tells Stefan that if he turns in the remaining three stakes she and Klaus will let them live. Later, Damon goes over to Alaric's to get the last stake but Alaric can't find it. Its been moved from its hiding place behind the bookshelf. After snarking Alaric for hiding it in such a cliched place, Damon asks if Alaric is really telling him that he is missing a stake that could kill his line of vampires. Alaric tells him that is what he's saying.
Damon and Stefan worry after Bonnie shows up with news of Alaric and it is revealed that Elena is missing. Stefan, Damon and Klaus finally agree to save Elena and Caroline together. As they fight Alaric, both Damon and Stefan are beaten as Klaus takes Elena. Later on, Damon, Stefan and Tyler begin to desiccate Klaus' body with help from Bonnie. Damon helps Elena up and takes her out of Klaus' manor. As Damon and Stefan take off to put away Klaus' body they talk about Elena and Stefan mentions that if she chooses Damon he will go away and let them be happy. Damon agrees to do the same and implies towards the trouble they go through for "one girl". Stefan responds saying, "She is a pretty special girl" and Damon agrees. This episode reflects one of the strongest points in the relationship between both brothers.
That night, Elena has one final talk with Damon, letting him know that she is choosing Stefan. Damon is hurt, but accepts her decision. He reminisces about the past, revealing that it was he who met Elena first, not Stefan. Damon saw her there on a road and mistook her for Katherine. He told her about what she really wanted: a love that consumes her, passion and adventure, and even a little danger, before compelling her to forget meeting him.
Much later, in a fight with Alaric after leaving town, Alaric dies. Damon realizes with horror that this means Elena is dead. He begins to break down, realizing that he has lost his best friend and the girl that he loves. He goes to the Mystic Falls Hospital, demanding to know where Elena is. Meredith tells him that she injected vampire blood into Elena to heal her cerebral hemorrhage, and that she would have died without her help causing him to be upset and shocked.
In Growing Pains, Damon is with Elena and Stefan in Elena's room, explaining to her that she died with vampire blood in her system and that she is in transition. He speaks bluntly and tells Elena that she has two options: to feed and become a vampire or die. He visits Rebekah and tries to stab her with the white oak stake. Rebekah unhands him easily but someone else shoots her in the back with an arrow, and Damon escapes. Damon, Matt, Dr. Fell and Liz meet at the Gilbert house and try to sort out where Caroline, Elena and Stefan could be. Matt realizes they could be locked up at Pastor Young's ranch, so he and Damon leave to check it out.
Damon and Matt arrive at the ranch, and instead of going on the offensive, Damon lures the pastor out by viciously biting Matt. After being shot, Damon plays possum, kills the officers that approach him, then turns his attention back to Matt, threatening to kill him.
When Damon is apparently about to kill Matt, Elena attacks Damon to stop him, revealing that she has completed her transition and is now a vampire. She tells him she remembers everything he compelled her to forget, including the fact that she met him first, though she alludes to the fact that it wouldn't change anything. She asks Damon what he would have done if he had been in Stefan's position and he answers with the truth: he would have let Matt die to save her. He asserts his own selfishness, saying that he would have been selfish enough to let her friend die so that Elena could have the life she wanted: a human one. After he reminds Elena of another compelled memory she got back, she doesn't respond and Damon leaves.
In Memorial, Stefan wants Elena to get used to animal blood right from the start and Damon disagrees with this approach. They argue about it until Elena arrives, and Damon tells Elena that, now that she's a vampire, she should be a vampire and feed on human blood. After the news comes out about the explosion at the Young farm that killed the town council, both the sheriff and Elena ask Damon if he did it, but he denies it. Elena also confesses that she has been having trouble keeping blood down, and asks Damon for help. After she refuses to drink from a human, Damon offers his own blood, but asks Elena not to tell Stefan about it.
Later, Damon gets a call from a frantic Elena, asking him to bring her a change of clothes. When he shows up at the church, he finds Connor sitting just outside the bathroom where Elena is. Damon manages to hand Elena a bag of her things without Connor seeing the bloody mess she's made, and waits until Elena is ready to go, making tense small talk with Connor. Outside, Damon tries to get Elena to drink from a blood bag, but once again she can't keep it down. Elena starts to get hysterical but Damon calms her down and she goes back inside the church. Stefan meets Damon outside and they argue again about what is best for Elena. Damon reveals that she hasn't been able to keep blood down for days, and casually mentions that Elena drank from him earlier.
Later, after Connor opens fire on Tyler in the church, Damon goes after him and catches up with him in the parking lot. He rips the door off Connor's truck and pulls him out, but Connor fires at Damon with wooden bullets and is about to stake him when he hears Stefan coming. Choosing flight over fight, Connor makes away in his truck. Rather than pursue Connor, Stefan stays behind with Damon and starts to help him up, but then sucker-punches him instead. Damon is indignant at first, but Stefan tacitly indicates it was payback for letting Elena feed from him.
That evening, Stefan gathers everyone together for a Japanese lantern ceremony. Damon doesn't think they should put the brakes on finding the hunter, but Stefan insists they take the time to grieve. The group takes turns releasing a lantern into the sky after memorializing lost loved ones, but Damon refuses to participate and leaves. Instead, he grieves in his own way at Alaric's grave alone, "talking" to Alaric about everything that's going on and, in a roundabout way, how much he misses his friend. Unbeknownst to Damon, Alaric’s ghost sits beside him the whole time, listening.
In The Rager, Damon and Stefan banter about being in a fight because Damon blood-shared with Elena, and Damon reveals his intention to take down the hunter and then leave town. He takes it upon himself to snoop around Connor's trailer, but quickly gets caught in one of the hunter's booby traps: if he moves so much as an inch, the trap would detonate strategically placed bombs. He calls Meredith, who arrives and helps cut the arrow out of Damon's back. While she works, Damon ignores a phone call from Elena, and Meredith comments that Damon is a good brother. He objects, but she points out the good in taking on the dangerous, necessary jobs so that Stefan can mentor Elena.
When Damon returns to the boarding house, Elena is in his room ostensibly looking for bourbon, but he quickly calls her bluff and says he knows she is looking for the white oak stake. He starts undressing in front of her, and when she doesn't leave asks her suggestively if she'd like to stay for the show. Elena snaps out of it and leaves, announcing her determination to find the stake.
After Jeremy has lured Connor to the hospital, Damon, having recruited Jeremy and Klaus in his plan to take down the hunter, traps Connor with a setup identical to the one that trapped Damon earlier. Even though he has an arrow in each arm, Connor still reaches for his gun. Just as he's about to pick it up, Klaus appears and kicks it out of the way. Damon and Klaus tag team their captive with an interrogation, but Connor remains tight-lipped. After Damon mentions Connor's invisible tattoo, Klaus seems intrigued. Connor tries to stake Klaus, but is easily disarmed. Damon observes while Klaus mentions something about Connor being one of the Five, but doesn't have time to find out what he means before Connor detonates the bomb and Damon is blasted into the hallway.
In the fallout of the explosion, Meredith chastises Damon for using the hospital in his dangerous plan and advises him to mend his relationships with Stefan and Elena. Later, when Elena is losing control while feeding on Matt, Damon vamp-runs into the house and pulls her off of him. Damon compels Matt to forget that Elena almost killed him and to go home, then turns to a distraught Elena and promises to help her learn how to be a vampire.
In The Five, Damon and Stefan search for more clues about the mysterious Five and the hunter, Connor, who is missing. Damon leaves Stefan to search for answers while he takes Elena to Whitmore College to learn how to feed. Under the guise of accompanying Bonnie on a visit to see the professor that took over for her grandmother, Damon hopes to teach Elena how to do the "snatch, eat, erase" method of feeding. She fails to bite her first victim after seeing a picture of the woman’s little sister on her phone; she loses her nerve and sends the woman away. Damon is annoyed, wondering aloud why Elena cares about a stranger. She reminds him that she's still herself and has the same feelings as when she was human. Bonnie arrives with a flyer about a frat party that night, and Damon is delighted at the chance to find Elena some victims she won't feel so sympathetic about.
That night they arrive at the ‘Murder House’. Decked out in costumes like the other party-goers, Damon and Elena have no trouble blending in and feeding at their leisure. Elena's first victim is a guy who had just slipped a roofie into a girl's drink. She lures him away from the action into an empty room and feeds on him. Damon coaches her, warning her not to kill him. She finishes and compels the guy to leave and forget what happened. Excited about her first successful snatch-eat-erase, Elena hugs Damon and tells him she wants more. They return to the dance floor, dancing and feeding on people, and then dance together, blood dripping from their mouths. Elena sees Bonnie return, snaps out of her blood high and runs outside, mortified.
Damon joins Elena and Bonnie outside. Bonnie accuses him of wanting Elena to be like him, and he argues that she already is and needs to learn to revel in the feed; not hating herself and enjoying it will be the only way she, like him, can make feeding fun and not get carried away. Damon walks away, leaving Elena crying about what had happened. He accompanies her home and she apologizes for letting things get out of hand at the party, confessing that she hates that, deep down, she agrees with Damon's point of view. She starts to say she doesn't want to be that way, and Damon finishes her sentence to say she doesn't want to be like him. When Stefan opens the door, Damon leaves.
In The Killer, Damon arrives at the Gilbert house to see Elena and ask about Stefan, who hasn't answered Damon's calls. Damon surmises that Stefan is dodging him after finding out about Elena dancing and feeding with Damon at the frat party, but Elena reveals she didn't tell Stefan about it. Damon teases her about being in a shame spiral, but they both get worried when Stefan doesn't even answer a call from Elena's phone. When Stefan finally shows up at the Lockwood mansion, Damon and the others already have a plan in motion to rescue Jeremy, Matt and April from Connor: Caroline and Tyler got the sheriff and the hybrids involved, and Damon asks Caroline to get Bonnie to help out as well. Stefan clashes with Damon about how to go forward with the rescue mission.
Later, up in Alaric's loft, Damon finds Alaric's map of the town's tunnels, one of which leads to the Grill. After a brief phone call with Stefan, Elena proposes to offer to trade herself for the hostages, since Connor does not yet know she's a vampire. Damon shoots down this idea, suggesting she wouldn't be able to handle a fight against a professional hunter. A mock fight ensues that ends with Elena straddling Damon on the bed, the crossbow pointed at his heart. She tells Damon that Jeremy is the only thing holding her together, and he promises that they will get him out. When Stefan rejoins them at the loft, Damon wonders aloud why Stefan has involved Klaus in his plan. When Damon suggests he's going to go rogue, Stefan stabs him with a vervain dart.
When Damon wakes up, he discovers Stefan stole his daylight ring. Elena decides that she's going to the Grill, and Damon tells her to get as close as she can before killing Connor. Later in the tunnels, Damon runs into Stefan, who has Connor. Damon immediately wants to kill the hunter, so Stefan tells Connor to run as fast as he can. Stefan tries to restrain Damon, but Damon eventually thrusts his hand into Stefan's chest and grabs his heart, threatening him until he confesses what he's been up to with Klaus. Stefan finally reveals that there's a cure to vampirism and Connor's tattoo is the key to finding it. Damon releases Stefan, shocked.
Later, Elena is crying while she digs a grave for Connor in the woods. Damon and Stefan try to soothe her, but she wants none of it. Back at the boarding house, the brothers agree not to tell Elena that she killed her chance at becoming human again. Stefan mentions a plan to go forward with finding a new hunter, and Damon says he will help, but he wants to know one thing: Does Stefan want to cure Elena because she's not cut out to be a vampire, or because he can't love her if she one? Stefan says he'll always love her, but she's not supposed to be a vampire. Damon makes it clear that he's fine with her either way, so if he helps find the cure, he's doing it for Stefan.
In We All Go a Little Mad Sometimes, Damon arrives at the Gilbert house after Elena called him, though he wonders why she asked him to come and not Stefan. Elena admits she doesn't trust Stefan at the moment, and Damon in turn admits that he called Stefan as the younger Salvatore walks in the front door. After Elena finishes showering, she has another hallucination, and this time she imagines that Damon is Connor. She bolts out of the house, where Klaus grabs her and speeds off. Bonnie meets up with Damon and Stefan and they ask for her help in breaking the curse Elena is under. She says the spirits won't let her do that kind of magic to break the curse, but she suggests that Shane might be able to help.
Later, Damon waits to meet Bonnie and Shane in Alaric's old classroom, where, alone for a moment, he reminisces about his friend. Bonnie and Shane arrive and Damon shows the professor the drawing of the hunter's mark and asks if he knows anything about the Hunter's Curse. Shane explains that if a hunter is killed by that which he hunts, the killer will walk the world in torment until a new hunter is awakened and the legacy is passed on. Damon realizes this means Jeremy has to get involved, and he and Bonnie explain to Jeremy he needs to kill a vampire to break the curse. Stefan calls Damon to ask him to find Elena, who has escaped.
Later, he finds her on Wickery Bridge, and somehow she sees that he's really there. Jeremy and Stefan kill the hybrid Chris in time, ending Elena's hallucinations. Damon is relieved, but soon realizes their new problem is that Elena ditched her daylight ring, and the sun is beginning to rise. She panics as her skin starts to blister, and Damon grabs her and jumps off the bridge into the water.
Later, Elena wakes up in her bed at home with the daylight ring back on her finger, and Damon explains that he fished it out of the river. She takes his hand and thanks him for saving her life. The moment starts to feel more intimate, so, realizing the awkward position he is in, he pulls back and tells her about the cure, the reason behind Stefan's secrecy lately.
Back at the Grill, Matt approaches Damon with information he had found out about the explosion at the Young farm. Having heard from April that the pastor knew Professor Shane, who suspiciously knew about the hunter's mark and curse, Matt decided to have Sheriff Forbes check the pastor's phone records. The pastor had made a call a day during the last month that he was alive, and 10 calls on the day of the explosion, all to the same phone number—Shane's office.
Later, Stefan and Elena break up, and their conversation has a lot to do with Damon. They talk about trust, and how Elena seems to rely on Damon more lately, instead of turning to Stefan. Elena admits that since she has become a vampire, everything she felt for Damon as a human has become magnified. His suspicions confirmed, Stefan breaks it off, and Elena agrees.
In My Brother’s Keeper, Damon learns about Stefan and Elena's break up. He offers Stefan his support, but Stefan brushes him off. Later at the Miss Mystic Falls pageant, Damon advises April on which dress to wear, and Elena changes her earlier opinion to agree with him, which Caroline finds bizarre. Elena follows him out of the room and down the stairs. He tells her he knows about the break up, but that he can't say he's sorry to hear it. Elena tells him Damon was the reason they broke up, and he is clearly surprised. They gaze at each other for a long moment, but Shane breaks them out of it and asks to talk to Damon. Damon leaves, glancing back to smile at Elena. Outside, after skirting around the issue, Damon accuses Shane of convincing the pastor to blow up the council. Shane stonewalls him and walks away.
Later, Elena is worried about Jeremy, but Damon assures her that Jeremy's probably fine. Damon confirms with Stefan over the phone that Stefan is with Jeremy and getting him to kill vampires. He later finds Tyler and suggests that Hayley talking to the professor is suspicious. Cornering the professor again, he threatens to kill Shane unless he gives up the name of another hunter, and instead Shane reveals that a Bennett witch is needed to get to the cure.
During the pageant dance ceremony, Damon and Elena catch one another's eye and smile at each other. Later, Elena moves into the boarding house, no longer safe living with Jeremy, and Stefan leaves for the night. Over drinks, Elena vents about the strain her new vampire status has put on her relationships with Jeremy, Stefan and Caroline, and her doubts about being cut out to be a vampire. Damon responds that he's never seen her more alive. Elena admits that she had wanted to dance with Damon earlier, remembering their dance at last year's pageant, and so Damon stands up and offers Elena his hand. They share a slow, intimate dance which escalates into passionate kissing and clothes-ripping, and finally they have sex with each other for the first time. Back at Caroline's house, Stefan and Caroline figure out that Elena is sired to Damon.
In We’ll Always Have Bourbon Street, Damon awakens the morning after he and Elena finally consummated their relationship. He admits to Elena that he's happy, and they have sex again. When Elena leaves for school, Damon makes one request -- that they wait just one day before they tell Stefan about them. Stefan arrives just as Elena is leaving, and he confronts Damon with his theory about the sire bond. Damon resents Stefan for suggesting it and wants to dismiss it completely, but Stefan only asks that Damon test the theory by asking Elena to try drinking from a blood bag again, and to emphasize that it would make Damon happy if she did. Damon reluctantly agrees to try, though he makes it clear that if Stefan is wrong, he should be very sorry indeed. Damon meets Elena at school and gives her a blood bag. She's doubtful that it will work, but when she is able to drink it without a problem, she's thrilled. With the sire bond seemingly confirmed, Damon is dismayed, though he doesn't let on to Elena what is going on.
Damon returns to the boarding house to look through some of his old things, and Stefan finds him in the midst of his search. Damon explains that this had happened to him once before, back in 1942 in New Orleans, when a girl named Charlotte was sired to him. Seeking a way to break the bond, he had enlisted the help of a witch named Valerie LaMarche. The brothers head to New Orleans looking for answers to their current problem, and reminisce about the time they briefly reunited in 1942 before Stefan left for the war. They arrive in the French Quarter, and continue to be at odds about the sire bond and Elena's connection to Damon.
They arrive at the address Damon had for the witch in 1942, as Damon couldn't remember where her shop was and they needed a place to start. Stefan suggests they look for Charlotte after Damon admits that the last time he saw her, he'd told her to count every brick in every building in New Orleans and he'd meet her at the corner of Bourbon and Dumaine—and he was gone by morning. After Stefan makes a comment about seeing how literal the sire bond is, they head to the corner and continue to argue about how to handle the sire bond and telling Elena. Damon, frustrated and angry with Stefan, leaves to get a drink and blow off steam, but on his way he is attacked by another vampire. Stefan hears the commotion and rushes to Damon's aid, but it turns out to be Charlotte, who hadn't attacked Damon but kissed him. She reveals that she has been counting the bricks of New Orleans all these years, but insists that she's not crazy and has lived a life beyond that as well. Damon and Stefan enlist her help in finding the witch's shop.
Later, they enter a shop and ask the shopkeeper, Nandi, for a spell that could break a vampire sire bond. Damon insists that the witch Val had had a grimoire with a spell to do it, and recounts the time in 1942 that he had visited the shop and Val had told him of a spell that required the sacrifice of 12 human souls. Nandi says she doesn't practice at all, and all of her grandmother's grimoires were lost during Hurricane Katrina. The brothers leave the shop, though Damon knows Nandi was lying—he recalls seeing a young girl in Val's shop whose name was Nandi, so she must have used magic to slow her aging. Damon reenters the shop angrily demanding her help, and she retaliates by using magic to cause Damon pain until Stefan steps in and brings the negotiation back to talking. Nandi explains that her mother had used Damon to access the power left behind by the sacrifice in order to practice a brand of magic called Expression. She also reveals that a sire bond cannot be broken with magic, that a vampire only develops a sire bond with her maker if the feelings were there when she was human, and vampirism only heightens those emotions. The only way around the bond is to sever all ties with the person in question - to tell her to live her life without him, to never think of him again, and to stop caring for him - and he must never see her again.
Before the brothers leave New Orleans, Damon does his best to set Charlotte free, telling her that it would make him happy if she could forget about him and make a life of her own. He leaves her and rejoins Stefan, who worries that Damon won't be selfless enough to do the same with Elena. Damon responds by recounting what really happened in 1942 when Damon never showed up to leave for war with Stefan: Lexi had convinced Damon that Stefan would be better off without him, and that he should think about what was best for Stefan instead of himself. Stefan seems touched to learn of this, and assures Damon that above all he wants Elena to have her free will back.
Damon arrives back at the boarding house to find Elena cleaning up after girls' night. She already knows about the sire bond, and asks if he and Stefan found a way to break it. Damon implies that there is no simple fix, but before he can try to set her free, she insists that she's happy and the sire bond doesn't change anything between them. Damon believes the opposite, and professes that although he usually doesn't do the "right" thing, he has to do right by Elena because he loves her. To strengthen her case, Elena takes Damon's hand and holds it against her heart, and they look at one another as they contemplate how to know what is real and what isn't, silently considering the future of their relationship.
In O Come, All Ye Faithful, Damon awakens next to Elena in his bed. Although he had not sent her away to free her from the sire bond, he refused to have sex with her. They instead slept beside each other, fully clothed. Still, Damon feels guilty about not following through on his promise to Stefan. Elena insists that their relationship feels real to her, and she dares a reluctant Damon to send her away. He deflects by bringing up their other problem - that Stefan doesn't yet know they had sex. After their discussion about how to proceed leads to an almost-kiss, they are interrupted by Elena's phone. Elena says she has to meet Bonnie, who is trying to teach Jeremy not to kill Elena. Elena asks Damon if he wants to come.
At the Gilbert Family Lake House, Jeremy is chopping wood when Elena and Damon pull into the driveway. After Bonnie takes a tensed-up Jeremy inside, Damon sees Shane standing in the doorway and wonders aloud what he's doing there. Elena reveals that she invited him to help with deprogramming Jeremy's hunter instinct. They approach the house, but it is now in Jeremy's name, so he has to invite them in. He does, and immediately tries to stake Elena. She disarms him easily, but it's clear that they have their work cut out for them.
Later, Stefan calls Damon to tell him the sword is missing. Damon flippantly suggests two plans involving killing Tyler to stall the plan to kill Klaus. Changing the subject, Stefan asks sensitively if Damon knows where Elena is, assuming that Damon had sent her away after they returned from New Orleans. Damon responds vaguely about her possibly helping deprogram Jeremy. Later, after the first attempt to hypnotize Jeremy fails, Elena sits on the dock and tells Damon how strange it seems that the last time she'd been there, she was so in love with Stefan, and now that's barely a memory. She wonders aloud whether this was the sire bond, or just being so happy to be there with Damon. This conversation, apart from making Damon uncomfortable, gives Damon an idea: Shane should have used someone other than the person Jeremy wants to kill to attach Jeremy's "detour feelings" to. He goes inside to suggest that they use Bonnie as Jeremy's detour whenever he feels the need to kill Elena.
Outside, Shane and Elena talk about her relationship with Damon. After Shane shares with her that he had lost his family, Damon interrupts them to threaten Shane's life (again), but Shane diverts their attention with another reveal: that he knows where the cure is because he has already been there. Later, Shane tells Damon and Elena the story about Silas and how he was trapped with the cure; thus, in order to find the cure, they need to find Silas. When Jeremy's mark is complete, it will contain the spell needed to dig up Silas. He refuses to reveal Silas' location, using it as leverage against Damon killing him. Damon calls Stefan with the news that they no longer need the sword. Alone again, Damon tells Elena his theory about Shane having orchestrated the massacre at the Young farm. Shane enters and makes excuses about the pastor being depressed and coming to Shane for supernatural assistance. They are interrupted by Jeremy and Bonnie, who are ready to test Jeremy's control around Elena. Jeremy walks toward Elena with a wooden stake in his hand and Damon steps in between them, but Jeremy, after looking at Bonnie for reinforcement, hands the stake to Damon. Jeremy reaches Elena and hugs her.
As Damon watched Elena and Jeremy decide which Christmas ornaments to bring back to their house, Damon sat outside on the deck and watched her. Elena took out plastic mistletoe and wanted a kiss, but Damon wouldn't do it. He said it was good to see her normal like that with her brother. He wants that for her. The truth is, of course, that Damon wants that with his brother, too. He misses celebrating Christmas with Stefan, which used to be their favorite holiday when they were human. Damon was ready to do the right thing: He told her she's gonna go home. He's gonna stay there with Jeremy and teach him how to hunt, protect himself, and kill vampires without her. "I’m setting you free Elena. This is what I want. This is what will make me happy," he said.
Later, we saw Jeremy thank Bonnie and hug her goodbye. Bonnie was going to drive Elena home. Elena told Damon she was prepared to fight him on this, but suddenly, every part of her body was telling her she needs to get in the car and leave him. She kissed him goodbye. Simple and gentle, they clearly felt the kiss, but she was very confused about the intense push to leave him still. Damon was surprised by the kiss, but still saddened that he had to send her away.
In After School Special, Jeremy and Matt sparring lakeside in tank tops while Damon listened to a voicemail from Elena for presumably the 100th time. Jeremy wanted Damon to teach him something new -- and what we learned was that Jeremy is still no match for a vampire. A pizza delivery girl arrived, for the third day in a row. Damon told her not to return, no matter how much the boys begged. Damon wanted to finish that message from Elena, who misses him and wishes he'd let her come to him, so he told Jeremy and Matt to run around the lake twice.
Later, Jeremy practiced slowly loading a gun while Damon fished for information on Elena's mood. Their conversation was interrupted by Klaus, who wanted to know how many vampires Jeremy had killed. He needs that hunter's mark to grow so he can find the cure and make more hybrids (since he just murdered 12 of them). Damon said Jeremy wasn't ready, and Klaus said he wanted to help. So Damon told Jeremy to watch and learn -- and then he fired two bullets into Klaus. "That was for Carol Lockwood," Damon said.
Meanwhile, Damon's sitting in the woods outside of the Gilbert lake house, whittling. Klaus vamps up. Surprisingly he's not mad that Damon shot him. He's more worried about Jeremy's hunter mark. He suggests they turn more townspeople so Jeremy can kill them and grow the mark. Damon hesitates and Klaus accuses him of trying to appease Elena by doing the right thing of not involving innocent civilians. Damon doesn't deny it. So Klaus tells him he's already started working on his idea. His first victim is the local pizza delivery girl. Earlier that evening he'd turned her then compelled her to go to Jeremy's house. While Klaus and Damon sit in the woods, Pizza Girl knocks on Jeremy's door, claiming car trouble. Too honest for his own good, Little Gilbert admits that he's about to hop in the shower then he invites her inside to wait for the mechanic. Pizza girl attacks Matt faster than you can say “extra pepperoni, please.” Jeremy hears the struggle, comes in and stakes her. Damon vamps in and together they all watch Jeremy's tattoo grow.
Elena called Damon on the phone and had a heartening discussion about her feelings for him. For the first time she confesses that she loves him. He promised to find the cure for her and would maybe do things she wouldn't like, but it was for her. And, then he asked her to come see him. Jeremy, Matt, and Damon showing up at a bar littered with patrons Klaus had in transition to become vampires. He thought Damon was going to convince Klaus there was another way to do this. "Well, I thought about it," Damon said, "and then I realized his idea was better."
In the next episode, Catch Me If You Can, Damon was disappointed that Jeremy wanted to retreat from the newly turned vampires, but then he softened -- caring about Jeremy and Matt. Damon said he’d slow the vamps down and ripped one's heart out. When Elena arrived, she was naturally upset with Damon, but she agreed to let him stay with Jeremy and go hunting while she took Matt home. Damon and Jeremy headed back to the bar to hunt the new vamps. Damon told Jeremy, "I'm trying to keep you alive, dumbass." Inside, they followed a blood trail -- and found a pile of dead bodies. Kol was there, looking adorable as always. He still had blood on his hands when he offered the guys a drink. "He's underage and I don’t like you," Damon cracked.
Kol cut to the chase and told them that finding the cure risks the awakening of Silas. Damon didn't care so much. So Kol continued: A few hundred years back, he came across a group of Silas' followers. They said Silas would rise again and trigger the end of all time, which sounds dangerous even to an immortal. So he murdered all of them. He can’t sit back and let this race for the cure happen. Kol didn't want to kill Jeremy and suffer the hunter’s curse. So he decided to rip off his arms. Solid plan, actually. Damon told Jeremy to run and fought Kol. Kol had Damon slowly staking himself to confirm that Damon could be compelled. Kol told Damon he wouldn't remember him saying this, but he was to find Jeremy and kill him.
Later Damon went to see Elena and asked where Jeremy was. At the Grill, she said, checking on Matt. Damon said he should go apologize to Jeremy for being tough on him. At the Grill, Jeremy senses something was up with Damon when they came eye-to-eye. He started after Jeremy, and Elena called Damon's name and he stopped -- for a second. He told Elena that Kol must have compelled him because if he finds Jeremy, he'll kill him. He saw Jeremy had gone down in the tunnels they used when Connor took hostages at the Grill. He followed. It's deliciously creepy that while Damon was hunting Jeremy, he was yelling ahead to tell him to run and get out of there because he was coming and going to kill him. Jeremy stopped in the tunnels and cut his hand and let it bleed on his jacket. Damon smelled the bait and when he picked up the jacket, Jeremy attacked him. Damon bit Jeremy's arm and tossed him. Damon said Jeremy was stupid, he couldn't fight him in close quarters. "Worth a shot,” Jeremy said, and he shot Damon twice in the stomach. Damon told Jeremy to shoot him in the heart because he won't be able to stop himself from coming after him. "Do it. Do it," Damon said. He lunged at Jeremy, and he fired a shot.
Damon woke up and Jeremy had shot him in the head. Damon thought Jeremy was stupid. Damon was still on the hunt. Jeremy ran through the woods bleeding. Elena caught up to Damon and tried to tell him that he can resist the compulsion because she loves him, and he loves her, and he'll do anything for her. "Sorry, Elena," he said and continued the chase. When he found Jeremy, Damon again did the most decent thing he could. "Shoot now," he told Jeremy. Jeremy fired a shot, and Stefan pushed Damon out of the way. "Hey brother, long time no see," Stefan said. And he snapped his neck. Damon was taken back to Salvatore Mansion and drained of most of his blood to weaken him. He couldn't even get off his back. He wanted to see Elena, but Stefan said they can't let him do that because with the sire bond, he'd be able to get Elena to let him out. Stefan's plan: Damon stays in there until they find the cure and the sire bond and compulsion are broken. Then Elena and Damon can do whatever they want.
In A View to a Kill, Damon, who was still on the ground in the Salvatore family cellar. Stefan tossed him a vial of blood and offered him a bottle of water. When Damon got up, he was greeted by Klaus, who was going to play the role of Original Babysitter. Stefan told Klaus to give Damon a vial of blood every couple of hours so he doesn’t desiccate. He gave him permission to bleed him out again, if needed. Damon told Klaus that Stefan was still mad at him for sleeping with Elena, and Klaus told Damon about catching Stefan sneaking out of Rebekah's bed. Revenge sex, Damon knows it well. Klaus was inside the cellar with Damon villain-bonding. Klaus asked Damon how he gets Elena to overlook every horrible thing he’s done: “What is it you say to her?” Damon knew what this was about: Klaus is afraid Caroline won't forgive him for killing Carol Lockwood. Damon gave him a real answer: Damon is the bad guy so things get done, Klaus is a bad guy just to be a dick. "If you're gonna be bad, be bad with purpose; otherwise, you’re just not worth forgiving."
Klaus, meanwhile, freaked out after Kol called him and asked Damon what Stefan and Elena were planning. Damon genuinely didn’t know. Klaus thought he'd compelled Damon to stay in the cellar, but Damon had been drinking that bottled water Stefan gave him, which had vervain in it. Damon was reunited with Elena now that he’s no longer compelled to kill Jeremy, and Stefan arrived home with Silas’ headstone. Elena assumed Rebekah was daggered so they just needed to get Professor Shane and they’d be set -- but Stefan said he didn’t dagger Rebekah because she's on their side. How could he trust her? Damon was more than happy to tell Elena that Stefan had slept with Rebekah. Elena had nothing to say until the brothers started bickering, and then she told them to stop. “Why don’t you tell her to calm down, Damon. You've managed to use that sire bond pretty well so far, haven’t you?” Stefan said. Damon punched Stefan. Then Jeremy screamed and ripped opened his shirt. The mark grew, and now they all could see it. “Here we go,” Damon said.
After arriving at the island, Shane offered Damon sunscreen with Damon asking, "Is that suppose to be a joke?"Damon declined to tell Elena if he’d take the cure when it's found. On the island, the hiking began. Rebekah recapped what everyone brings to the table including Elena (nothing) and Damon (“nice behind”). When Shane skated the question of whether Bonnie should trust him, Damon pressed for answers. What Shane means is that after his son died in a car accident, his witch wife tried to resurrect him with Expression. It overwhelmed her, and she died. Bonnie was understandably pissed that Shane taught her the same magic that killed his wife. But his wife, Shane said, was undisciplined, and he’s learned the warning signs so he can keep Expression from consuming Bonnie. That’s why they can’t kill him once he points to the cure: Bonnie needs to keep him alive so he can keep her alive.
The gang came to their camp for the night. After Shane made a comment about Damon having the most to lose when they find the cure, Elena had to assure him that her love for him won't change. She clearly wants him to take the cure. In the morning, the group had to split up: Bonnie wanted to stay behind and try a locator spell, Shane wanted to stay with her, and Damon wanted to stay with Shane. Shane used the satellite phone he said earlier no longer worked, which set Damon off. He demanded to know where the cure is, and Shane said it and Silas are entombed in caves deep beneath that well. Flashback: Shane's wife told him that if he helps raise Silas, Silas will help those who've helped him, which means Shane can raise both his wife and their son, Sam. She explained the necessity of the hunter's mark, the spell, and the power of a descendant of Qetsiyah. He asked about the massacres. Flashback: Shane's wife told him that he wouldn't have to perform three massacres of 12 himself -- he just had to convince someone it was possible for them to see a loved one again, too, and they'd do it for him. They’d all come back, too, she said. Damon counted two massacres -- Pastor Young's, so he could see his wife again, and Klaus' holiday hybrid spree. Shane assured Damon that he hadn't brought them all along to be part of massacre number 3, but he wouldn’t tell him where the magical well is.
Shane tried to tell Damon he should leave the island rather than watch Elena find the cure and choose Stefan. He assumed Damon wouldn't kill him because then Bonnie would die when she did the spell to access the cure. But Damon doesn't care about Bonnie, he told Shane. And right before Damon snapped his neck, Elena arrived to stop him. She freed Shane and told him to stop messing with her friends. Damon finally admitted to Elena that he doesn’t want her to be cured. Even if she still loves him, she'll be human and he'll be a vampire, and they won’t work. She told him to take the cure with her so they could grow old together. That’s Stefan, not him, he said. He used to miss being human, but now he can’t think of anything more miserable than being human, then walked away. Damon went walking through the woods and got hit by an arrow. He realized it was from one of the Five from the mark on the guy's hand. The hunter snapped Damon's neck.
InDown the Rabbit Hole, Galen Vaughn, the Hunter who captured Damon, had him tied to a tree and wanted to know why his mark suddenly completed itself two days ago. Damon insisted he knows nothing about tattoos. "Look at my skin, it's flawless," he cracked. A new classic Damon line. Vaughn took a poker to Damon's neck to show he should be taken seriously. Vaughn now had Damon walking toward the well. His plan was to use Damon to make Bonnie open the crypt to Silas for him. He'd make Silas take the cure, kill him, and complete the Brotherhood of the Five's mission. Damon noted that Bonnie would not do anything for him, but good news for Vaughn: They didn't give a crap about Silas, they just wanted the cure, so yes, Bonnie would open the crypt regardless. Vaughn dropped the bombshell we all kind of saw coming: There's only one dose of the cure.
The Hunter and Damon officially entered the playing field. Since Vaughn no longer needed Damon because Bonnie had done her part already, they were ready to kill each other. Damon said he was going to do away with Vaughn and get the cure for the girl he loves. Vaughn said Damon's attachment to his friends would be the end of him. We heard a noise. “You don't know my friends,” Damon said. Enter Rebekah. “Or my enemies,” he finished. He knocked Rebekah out with some kind of stake grenade he buried in her chest and fired some kind of vervain yo-yo around Damon’s neck.
Stefan and Elena caught up, and Vaughn fled through the passage. Stefan sent Elena on, and he stayed behind to try to help Damon. Stefan finally freed Damon, and Damon insisted Stefan go help Elena get the cure while he sat, sulked, and recovered. Stefan didn’t waste time telling Damon that they had to save the dose for Klaus. Damon had crawled over to Rebekah and picked the stake shrapnel out of her back. She knew he hadn't gone with Elena and Stefan because he wanted Elena to have the cure, even if she may not love him back then, which meant he was being selfless with her and was now a "halfway decent person."
In Stand By Me, Stefan told Damon that because Jeremy was one of The Five, he's supernatural, so the resurrection ring would no longer work. Damon said Elena won’t survive this. He asked Stefan to take Elena off the island, and he'd look for Bonnie, who’d gone missing. Damon’s witch hunt was interrupted by a noise in the woods. “Unless you’re blonde, a Bennett witch, or a doppelgänger, I suggest you steer clear,” he said. Rebekah appeared shortly there afterward. He told her about Katherine’s return and Jeremy, and what Rebekah said: She's not heartless. She won’t miss Jeremy, but she knows he was Elena's only family and she understands loss. She wanted to find Katherine, but Damon said she’d be gone. They had to find Bonnie. Oh, and in case you were wondering, Silas is up and about.
Rebekah assumed Damon wasn't strong enough to handle a grieving Elena, and he used her as a shield to stop an incoming arrow from Vaughn. Damon caught up to Vaughn and knocked him out. Damon had a large knife to Vaughn's throat because he assumed Vaughn had helped Katherine “bone” him. They couldn't kill him, but Rebekah was prepared to go Zero Dark Thirty on him (which Damon always approves of) and Vaughn spilled everything: He was tracking vampire dens in Colorado when Katherine found him and said she could lead him to Silas. Katherine already knew about the Hunter’s mark and cure, having found Hayley in New Orleans. Damon left Vaughn with Rebekah, so she could pursue her lead on the cure, and he was off to find Bonnie. That really is why he stayed behind: He knows Elena couldn't survive losing her best friend, too.
Luckily, Bonnie walked out of the woods and found Damon, who hugged her. Bonnie and Damon drove up to Elena's house, and Damon immediately told Caroline to get him Stefan. Apparently Bonnie had shared her plan with him on the trip home. Damon told Stefan about how Bonnie needed to complete the Expression Triangle in order to gain enough power. She mentioned about dropping the veil between this side and the Other Side, so all supernatural creatures have access and they can all see Jeremy, Alaric, Vicki and everyone that they ever lost.
Back inside the Gilbert House, Damon tried to get Elena to talk to him but she wouldn't listen to him. She went downstairs and asked for Bonnie. Matt was taking her home, so Elena said they'd have to do this the old-fashioned way. She wanted to burn the house down with Jeremy in it. It was a good cover story. Plus, she didn't want the memories of everyone she's lost. After Elena breaks down, Damon tries to calm her down and comfort her. Then he told her to turn off her humanity in order to help her. He said it would all go away. It's what he wanted her to do. She stared ahead.
Outside, Stefan told Damon it was a mistake to turn off Elena's humanity, since it was all she had left, and Damon said humanity means nothing if you don't have someone to care about. Stefan said she had Damon, and Damon said he wasn't enough this time -- she'd lost her brother. He truly thinks she wouldn't survive losing her brother because he couldn't. His plan is for them to keep an eye on her, and then Damon will eventually use the sire bond to bring her humanity back. Damon told Stefan their differences over Elena mean nothing now, and Stefan started to tell Damon what he couldn’t actually say -- I love you. Damon said he knew and put his hand on Stefan's shoulder. The brothers went back inside to find Elena with another lit match. This was still the best cover story, she said. Stefan tried to tell her that maybe one day she'll want to come home, but she said she wouldn't. She dropped the match, and then they all walk out as the flames built.
After a few days, Damon in Bring It On, is out on the road with Elena while she pretends to play dead and feed off of her victim. Damon stopped her from nearly killing the woman and had to ask her to show a little restraint. They'd agreed no killing. The next morning at the Salvatore Mansion, we learned that house has the only vervain-free water supply thanks to their fancy filter. While Elena showered, Caroline, Damon, and Stefan made their game plan: Damon would work on finding Katherine and Caroline would take Elena to school for some normalcy. "Sounds like fun," Elena said, not yet wearing the towel she had with it. "What, it's nothing you guys haven't seen before," she said to the brothers. She was fine with the school plan because she had nothing else to do. They all assumed the sire bond was working and trusted that she wouldn't feed there because Damon asked her not to.
Having obtained Klaus' phone records off-screen, Damon paid Klaus a visit to tell him he sucked at two things: Find Katherine and covering up his secret phone conversations with Hayley. Damon tried to convince him to let him speak to Hayley since they're back on the same side again: Katherine most likely wants to shove the cure down Klaus' throat, which neither of them wants to happen. Klaus said Hayley was off-limits but told him about the vampire who should soon be dying of a wolf bite who'd attacked Hayley on Katherine's behalf.
Stefan called Damon, and we got the explanation: the sire bond was based on her feelings for him, so without her feelings, the bond was gone. Damon was busy anyway. He was now at the truck stop, where he was quickly joined by Rebekah. She was back from the island, where, she told him, she saw Shane's dead body. Now she's looking for Katherine, too. They joined forces because she'd brought some of Klaus' blood, which they could use to save the vampire and interrogate him about Katherine. Damon and Rebekah had made their way to the Grove Hill medical center, where Damon believed the wolf-bitten vamp would go to avoid the fun and feed. After seeing the blood supply there was gone and thinking about what Stefan had told him about the Mystic Falls hospital having been robbed, he figured they had another vampire to worry about -- but not now. Rebekah distracted him by telling him that he's better off if she gets the cure because if Elena takes it, she'll go back to Stefan. In Elena's current state, she's still leaning Team Damon.
Back at the medical center, Damon bit a nurse and sent her bleeding to her car as bait for the bitten vampire, who'd be looking for his last meal. Damon grabbed the guy and knew him. His name was Will. Will asked for help, and Damon ripped his heart out. He didn't tell Rebekah he knew him, he just said he was too far gone for help. She had to know he was lying. Damon arrived home and smiled at all the beauties there. He told Rebekah that losing the cure was the best thing that ever happened to her. If she wasn't a vampire, she'd just be ordinary. Stefan text Damon that Elena was AWOL and he needed help. The brothers arrived just in time to stop Elena from staking Caroline after a pretty badass fight sequence in the woods. When the Salvatores stepped in, Damon noted that under other circumstances, Elena fighting another chick would be a major turn on.
In Damon's bedroom, Elena sat impatiently as he looked for something that turned out to be a picture of him and Will. I assume the life mystery he spoke of was how Will knew Katherine. Elena was annoyed that Damon of all people was judging her when he's tried to kill Stefan multiple times. She told him she doesn't care how bad he is now, and that if he were to be honest, he likes her better like this. Next time we saw them, they were in his car on their way to New York City.
InBecause the Night, Damon told Elena that they were in New York City so she could feed -- “There's so much life, a little death goes unnoticed.” While Elena was off getting her hair done, Damon gave Stefan an update over the phone: He’s there because his buddy Will used to get fake IDs for vampires, and he thinks Katherine was one of his clients. He then saw Elena's new haircut and thought it was hot. Damon took Elena to Billy’s, the underground club he frequented in the '70s. He used to kill people to get their IDs for Will, and Will would let him feed in the club. Damon was asked to get a lot of 5’7” brunettes for Will to give a client who was a runner. In a flashback, he was about to feed when Lexi stopped him. “You got Lexi'd?” Elena asked in present day. And then Damon's head was down on the table. It was Rebekah, pissed that he left without her. Rebekah told Elena that Damon was there following a cure lead, but Damon seemed to save it. It was revealed that Stefan had heard about Damon being reckless all the way in Mystic Falls and sent Lexi to find out what had flipped his switch. Elena pretended she was mad because Damon was clearly going to try to Lexi her. He went to the bar, and Elena admitted to Rebekah that she was returning the favor and playing him right back. She wants to find the cure first so he and Stefan can't shove it down her throat.
Lexi didn't heal Damon with Bon Jovi concerts because she could feed with Damon. Flashback to them double-teaming a woman in the club, which is what Damon and Elena did now. He then relinquished his side of the neck to Rebekah. Elena saw Damon sneak off. He was in Will's apartment, Damon phoned Stefan as he searched Will's files. He thought the clients were filed under their birthdates, and he couldn't remember Katherine's. “June 5, 1473,” Stefan said immediately. He discovered a sheet of addresses for Katherine, mostly post office boxes. Elena found him, and they went back downstairs. She wanted him to finish his story about Lexi. Lexi had partied with Damon for months, and late every night, she’d torture him asking him to talk about Katherine. Love is the most powerful emotion, Lexi said, so she thought she could flip his switch if he’d just let himself remember what it was like to love Katherine. Lexi wasn’t giving up -- Damon had asked her to help Stefan back in 1864, and now Stefan had asked her to help him. Damon told her that the person he cared about wasn't Katherine, it was her. They had one hot and heavy night together that ended on the rooftop. Elena grabbed a bottle and wanted to hear the rest of the story on the roof. As Damon led her away, Elena smirked at Rebekah.
Elena made a move on Damon, telling him she'd never done it on a roof and that he didn't have to take the high road now because the sire bond isn't in play. She put her hand in his back pocket, which would have been hot had she not been looking for the sheet of addresses. Damon said he was trying to save Elena from doing the one thing when her emotions were turned off that she can’t take back. When he got his humanity back, Lexi was a walking-talking reminder of all the awful things he’d done. He avoided her until she showed up for Stefan's birthday that time. With the rush of memories came a rush of guilt. That's why he killed her. Out of sight, out of mind. Elena still insisted she's not taking the cure, and Damon assured her she would, even if they have to break her neck or tie her up till they find it. Rebekah was there to break his neck. Damon later wakes up and realizes that Elena is missing. Elena then calls him to tell that Rebekah and her have taken his car and are now going after Katherine for the cure.
InAmerican Gothic, an off-screen Sheriff Forbes proved efficient this episode: She tracked down Damon's car after Elena and Rebekah ran out of gas and abandoned it. She'd also tracked the car they'd stolen after it, so once Damon filled up the tank, he and Stefan were off to the cream corn capital of Pennsylvania, too. Damon was looking on the bright side of things: If Rebekah takes the cure, they can kill her. But then Elena is a vamp forever, Stefan reminded him. “Elena without humanity is a stone cold bitch, and I won’t trust her until we get the old Elena back,” Damon said. Finally, they're on the same page. Later, the boys showed up in the Pennsylvania town, and Damon again insisted that he's over vampire Elena and wants to do whatever it takes to get her home and to take the cure.
When Rebekah was breaking Katherine's hand, the boys sat down, and after Damon gloated about Katherine's predicament, Stefan asked where Elena was. The answer: Off getting kissed by Elijah, who believed she was Katerina. And that’s why Rebekah was reminding us how Katerina had come between Elijah and Klaus. Katherine came clean about her being “friends” with Elijah. Rebekah told Stefan where Elena was meeting “em,” and Katherine agreed to take Rebekah and Damon to get the cure. Katherine took Rebekah and Damon to a home that didn't belong to her. She tried to pretend the cure was stolen from her safe, but they weren't buying it. Rebekah took upstairs and Damon looked downstairs. He noticed the fish tank had no fish in it but a large treasure chest. When the water had vervain in it, he knew he'd hit the jackpot. Katherine dunked his head in the tank as he went to fish out the cure, and she almost got out the door before Rebekah stopped her. To save her life, Katherine gave Rebekah the cure and bolted. Stefan went at Damon, assuming he didn’t really want to stop Rebekah from taking the cure, but Rebekah gasping for air interrupted that. He threw a letter opener at her head, and she caught it. Her hand was cut, but it healed. She was still a vampire. Meaning the cure was still out there.
Damon admitted to Stefan that he had a moment of weakness and let Rebekah take the cure. But afterward, he realized what a mistake he'd made. Stefan said they can’t judge Katherine for repeating her past when they do it, too. Them falling for the same girl has to stop: Once they give Elena the cure, Stefan said, he wants to get her out of his life and get a new one of his own. Elena had called a meeting in the diner with Damon and Stefan to ask them whether they were going to respect her decision not to take the cure and accept who she is now. If not, there would be consequences, she said. The boys didn’t seem to hear that part. Stefan reminded her how she never gave up on him, so he’s doing the same. She asked for another refill and snapped the waitress’ neck. If they don’t let her be, they'll have more bodies on their hands.
In Pictures of You, Salvatore brothers tossing a football back and forth and talking about distributing the cure to Elena without instigating her to commit mass murder. Stefan suggests making her want the cure. The two brothers plot about how to get Elena's humanity back and they decide to bombard her with emotions. And Stefan admitted that it would be Damon to help her through it when she gets her humanity back. That night, Damon presents her with a corsage and she refuses to put it on her wrist so he does it for her. They get in the limo and drive off. The Salvatores and Elena walk into prom arm in arm. The decor is very elegant and nostalgic, which is emphasized by all the digital images of high school memories flashing on digital screens throughout the room. Suddenly, a photo of Elena and Matt from their first day of freshman year pops up and Elena’s face flickers with pain and recognition. “My mom took that when she dropped us off at school,” she reveals. And as that photo fades out and is replaced with one of her and Jeremy she becomes overwhelmed by the sight of it and dashes off.
Elsewhere in the room, Elena pulls out a flask and Damon swoops in to take it from her. “You’re underage,” he states. “You're overage and honestly it's kind of creepy,” Elena retorts. “Oh, c'mon,” Damon says. “What badass senior is complete without a prom date that’s slightly too old for high school?” “Please don't refer to yourself as my date,” Elena groans. “Oh sorry,” Damon says in a mocking a tone. “Your boyfriend.” Upon hearing the “b” word, Elena practically chokes on the hard liquor she's gulping down from the flask. “What are you doing?” she asks. “Trying to stir some feelings in me? Ironic since you, my Sire, are the one who had me turn them off.” She then tries to tear at his heartstrings by telling him that he’s nothing to her and that the only reason that she ever told him that she loved him was because of the whole sire bond. With those words, she walks away, breaking his heart again.
Damon then sees Stefan and Elena dancing and he is pain-stricken. Seeing Caroline is standing around looking lonely and Damon stands next to her with his flask. She laments about how the prom sucks and this is not how she wants to finish off her senior year. He offers her an understanding glance and some booze. “Well, if anyone asks, I'll be at the after party,” she states after taking a sip. At that very moment, Bonnie rushes in to tell the Salvatore brothers that Silas is appearing to her as Jeremy. The conversation is interrupted when April takes the stage to announce this year's Mystic Falls prom king and queen. Stefan suggests that they take Elena home but Damon refuses to because she's safer around people. And then April announces the winners — Matt Donovan and Bonnie Bennett. Damon and the others congratulate them. Damon is getting totally plastered. Stefan joins him and, right away, Damon bombards him about flirting with his girlfriend on the dance floor. Stefan reminds him that they're trying to retrieve her humanity: “I mean, I don’t mean to be a dick, Damon, but Elena and I have history. Memories, laughs, up and downs…it was a real relationship. I mean, what you had was a one night stand that was probably the result of a sire bond.” Damon vamp-speeds in for an attack but Stefan stabs him and says, "Your mind is a dark and riveting place, Damon.” As Damon keels over, clutching his wounded abs, he strains out, “Silas. Where’s my brother you psychic freak?" Silas casually tells him that Stefan is in a bit of pain in the woods as well. He pats Damon and walks away.
Damon, who has shaken off his stab wound from Silas, is in the woods searching for his younger brother. He finds Stefan pinned against a tree. “Let me guess, an extremely handsome man came up to you, claiming to be?” Damon jokes. While Bonnie tries to kill Elena, Damon rushes to Elena’s side as she whimpers, “Damon, help!” Stefan gently asks if she's okay and Bonnie freaks out, “I almost died, the shell of my best friend almost killed me, none of this is okay!” The Salvatores then inject a weak Elena with vervain. “Plan B,” says Stefan. As they lock Elena in the Salvatore board house cellar, Damon and Elena accidentally stumble upon a Plan C. Fear — which just happens to be one of those “pesky human emotions.” “I could see it in her eyes,” Damon contemplates. “Elena thought she was going to die. She was scared.” So they join forces to make Elena's life a living hell from now on and to work alongside Bonnie even though Damon is cautious about teaming up with her since he doesn’t want to underestimate Silas' influence on the witch. And then, out of curiosity, Damon asks Stefan what Silas had said to trick him? Stefan shrugs it off and says that fake Damon had led him out in the woods pretending to have seen Silas. Stefan then asks Damon what went down and he fabricates a story, “[He] talked about his hair. Figured that'd be you.” Stefan forces a quick grin and they make their way upstairs.
In The Originals, Elena is still in no humanity zone. Damon and Stefan are wondering what to do when Katherine walks in. She says Hayley, the werewolf girl, will get Klaus out of their lives for good. Later, Damon feeds Elena blood with vervain in it. He wants her to feel angry or mad or scared. Elena says it'll be interesting to see who breaks first.
In She's Come Undone, Damon gets into Elena's head and shows her all the normal things that she's missing out on, like high school, etc., to bring back old Elena, the girl who has feelings/has humanity all through his special vampire mind tricks and it doesn't work. Caroline, who tries her hand at turning Elena back to her old self, uses the made-up word "intervention-ing." When it doesn't work, she's come around to Stefan and Damon's more aggressive tactics.
Damon and Stefan turn to pain to get Elena back to the way she was, by pulling back the curtain and burning her. They're hoping that by inducing fear, the old Elena will return. "I'll hate both of you for it," Elena says before Damon settles on that unpleasant fact: "Worth the risk." Elena's rage is the first stage of the Salvatore brothers' planning at getting to her core. Instead, she hits targets Damon's sire bond and the fact that she was the one who dumped Stefan. Elena outsmarts the brothers by pulling back the curtains herself and catching on fire, proving to them that they actually wouldn't hurt her -- even though they've repeatedly claimed they would. It was Stefan's idea to bring Katherine in so they resort to using Katherine, their last chance, to scare Elena into some humanity. After Elena escapes the Salvatore cell, thanks in part to Katherine, Damon teams up with Matt to find her, and they come up with a plan along the way.
When Matt finds Elena, she starts feeding on him until Damon and Stefan arrive at the scene. threatens to kill her oldest friend if she doesn’t flip her humanity switch. “You're bluffing,” Elena replies, after which Damon snaps Matt’s neck. That finally does the trick as the emotionless vamp is overcome with tears. While she’s reeling at the idea that Matt is really gone, Damon reveals that her friend is wearing the Gilbert ring. This was all Matt and Damon's plan. Thanks to them, Elena got her humanity back.
In The Walking Dead, Damon and Stefan ended up at the hospital because Sheriff Forbes needed to be brought up to speed on Silas because at least five patients in the hospital had been drained of nearly all their blood. He was fueling up for something, they presumed. Later, Elena wanted to go searching for Bonnie with Damon. She wanted him to tell her where Katherine is. Damon ultimately did, because she's with Bonnie. Damon and Elena came inside, but he didn't want her to go underground because he was afraid Katherine would kill her or Elena would kill Katherine and then feel too much. So Elena staked him and went on her way.
As Damon struggled above in a hallway to get the stake out of his gut, someone walked up...Alaric. Need a hand?" he asked. Alaric pulled out the stake, but slight problem: Damon wasn't sure it wasn't Silas. "So this is either really good or really bad," Damon said. "It's good to see you, too, Damon," Alaric answered. He proved it was really him by opening up Locker 42, and taking out a bottle of their favorite booze. And they hugged. Alaric told Damon the veil is only down within the triangle, so not everyone has a reason to come back to Mystic Falls. Then Damon told Alaric to find Stefan.
Damon stumbled into Silas when he looked like Alaric and put a chain around his neck. Bonnie literally worked her magic and made Silas turn into stone again, like Qetsiyah had. He was becoming his true self, Bonnie said, before it was complete. Alaric and Damon were off burying Silas' body and having a drink themselves. Damon said he thought Alaric had cut back, and Alaric said he thought Damon would take care of the children. Alaric had found the cure in Silas' pocket and gave it to Damon. Damon didn't know what the hell to do with it. "Get the girl," Alaric said.
The day of Graduation, Vaughn shoots Damon with a werewolf venom-lace bullet. Vaughn is temporarily incapacitated after Stefan rips his heart out. Damon hands the cure to Elena, saying he wants her to take it, but she refuses. Now knowing that the sire bond is broken. When Elena figures out Damon is dying, Jeremy suggests that Damon take the cure, but he too refuses and leads Vaughn to dig up Silas. Stefan mentions that Damon is stalling because they haven’t moved Silas. When Vaughn almost kills Damon, Alaric shows up in time, throws Vaughn into the lake, and snatches the cure again.
Later, Damon is shown to be cured thanks to Klaus. Elena asked Damon if he was alright now and he told her he was fine then she slapped him which made Alaric proud and Lexi laugh. Damon was standing in front of the fireplace and said he wanted to apologize, but then realized he wasn't sorry. Yes, he'd rather die than be human, both because he didn't want to age and because he didn't want to age while she remained the same. He's selfish, and no apology would encompass all the reasons he's wrong for her, he said. Elena said she wasn't going to apologize either then. She's not sorry she met him. Not sorry that in death, he's the one who made her feel more alive. Not sorry that even though she knows it'll be the worst decision she's made, she's in love with him. "I love you, Damon," she said. And then they kiss passionately.
As Stefan is loading Silas' body into the trunk of his car, Damon comes out. After agreeing that the quarry will be deep enough to hold Silas's body, Damon offers to keep him company during the ride, but Stefan turns him down, saying that Lexi is going with him. As Damon heads back inside, Stefan tells him that he isn't happy with Elena's choice, but that he isn't unhappy for her and Damon either. Damon thanks his brother and goes back inside. Alaric is looking out the window and sees that the moon is full and that the ritual will soon begin. As Damon pours them a few drinks, Alaric smiles and says that he had finally gotten the girl. He then tells Damon that he'd better not screw it up. Damon looks down and says that with Alaric looking over him, he wouldn't. When he looks back, Alaric is gone.
Damon and Elena have spent all summer being together. While Elena was heading to Whitmore College, Damon promises her he will take care of Jeremy. When Katherine shows up and begs him to protect her as she feels someone is after her. When she picks up the phone and pretends to be Elena, she tells Damon about Jeremy's issues at school. Luckily for Jeremy, Damon is able to compel the principal to lower the charges to a three-day suspension. Unfortunately for them they soon realize they have bigger problems.
Silas walks into the bar as Stefan and greets Damon. He sits and talks but is only there to read Damon's mind. After getting the information he wants, he says bye to Damon, pats Jeremy on the back, and then heads to Salvatore Boarding House. Jeremy and Damon arrive just in time and Damon instructs Jeremy to take Katherine somewhere and not tell him. This leaves Silas to give Damon a crash course on why he looks like Stefan and to tell Damon what he did with Stefan. This leads Damon to call Jeremy and explain he's had a change of heart. Later, Jeremy is on the precipice of death. Damon finds is able to get to him in time, feed him vampire blood and hold him until he comes back to life. And Damon doesn't tell Elena anything that happened.
In True Lies, Damon is trying to find Stefan with the help of Sheriff Forbes. Later he is talking to Elena on phone when she sees Silas (who she thinks is Stefan) on campus. Damon tries to tell Elena that it isn't Stefan but she is compelled to hang up by Silas. Damon quickly hurries to Whitmore and visits Caroline and tells her that Silas is with Elena posing as Stefan, Caroline tells him about the nagging pit that Elena has about Stefan and he tells her that they have to go look for Elena.
Elena and Jesse are talking when Damon arrives and knocks out Jesse. Elena takes him to her dorm room, seduced him in order to tie him to a chair and ready for the kill but Damon figured out that Silas used his mind control power over Elena so he tried his best to make Elena resist the "rage" by thinking about her worries of Stefan. Later, Damon showed her that he'd snagged Stefan's daylight ring back from Silas the day before. And then Damon said he's secure enough in their relationship that her having psychic dreams about her ex-boyfriend doesn't bother him, but it still sucks. They kissed, and Elena told Damon they were going to save Stefan and she would still love him. Then they passionately kissed.
In Original Sin, Damon and Elena along with Katherine go in search for Stefan when Elena and Katherine both have a same nightmare about him. While traveling Katherine taunts Elena and Damon about their relationship,annoying them both. After reaching Jo's bar,the place which appeared in their dream, Elena and Damon happily leave a sleeping Katherine in the car.
In the bar, they find Jo whom has a bandage around her neck. Damon compels her to tell him what happened and she reveals about Stefan attacking her and then him burning before Qetsiyah threw him into a truck. She mentions how she knows who's truck it was and directs them to the hut.Before though she offers Damon a drink and he accepts until he realizes it is filled with vervain. Nadia comes in telling them that she threatened Jo's life if she didn't do it. After a violent confrontation with Nadia, Elena decides to save Katherine from Nadia while Damon goes to find Stefan. Before parting ways Damon tells Elena not to risk her life in saving Katherine as she is not even worth a hair on Elena's head and then they kiss.
Damon finally reaches the hut and finds Stefan tied up in veins on a chair. He tries to free him but can't. Stefan mentions how Qetsiyah is back. Qetsiyah reappears and tells them that she is going to create a link between Stefan and Silas so that she can disable Silas' mental powers. Despite Damon's reservations, Stefan agrees to it. She does the spell, in which she begins to fry Silas' brain. Stefan falls unconscious. Damon tries to wake him but it doesn't work. Qetsiyah reveals that he will wake up in time and then mentions to Damon how his relationship with Elena is doomed. She reveals how every incarnation of the doppelgängers, always meets and falls in love and conquers all, saying it is the doing of the universe. She mentions to Damon, that he can leave Stefan with her so that he can continue his relationship with Elena with no interference. But Damon decides to kill Qetsiyah, but she is able to knock him out. Qetsiyah leaves and Elena arrives and goes strait to Stefan not even noticing Damon. Damon is clearly hurt by this.
Back at the Salvatore house, Stefan is still unconscious while Elena appreciates Damon for being a good brother but he doesn't say anything. Elena asks what Qetsiyah said to him back at the cabin. Damon tells her about how she explained that the universe is working against them to bring Stefan and Elena together and so they don't stand a chance. Elena responds by saying that Qetsiyah is crazy and she won't let Silas' 2,000-year-old ex-girlfriend screw things up between them. Damon emotionally tells her how he won't let a stupid idea of destiny stop him from loving Elena or being with her or building a future with her because she is his life. Elena, touched deeply by his words, leans in to kiss him but they are interrupted by Stefan who wakes up and tell them he has no idea who Elena and Damon are.
In For Whom the Bell Tolls, Damon is helping Stefan remember his past.While enjoying a ride together Stefan assumes that Damon is the safe brother while Stefan is the fun one which amuses Damon. Then Damon flips the car and Stefan realizes Damon is actually the fun one. The next day in the grill, Elena visits them and she and Damon discusses about how to deal with Stefan. At the Salvatore mausoleum, Damon is honoring their dead family members by ringing the bell when he gets a text from Jeremy for meeting him alone and so Damon leaves.
Back at the house Jeremy is trying to tell Damon about Bonnie's death. He starts of by telling him that no one can be brought back from the dead without consequences and Damon starts to realize what he is hinting at. Damon begs Jeremy not to say it but Jeremy finally confesses that Bonnie is dead. Damon is furious and starts to walk towards Jeremy angrily looking like he is about to hit him but instead he hugs him.
Elena calls Damon to help him find Stefan while he is trying to tell her about Bonnie's death. They finally find Stefan back at the house but he is still upset with them as they didn't tell him about them being together and leaves the house. Elena tells Damon that they need Bonnie to fix Stefan's memory and Damon finally tells her about Bonnie's death which shocks her. Later, Elena is freaking out as she can't find a dress for Bonnie's funeral and breaks down into tears telling Damon how she can't do this again. Damon hugs her affectionately and tries to calm her down. At Bonnie's funeral Damon consoles Elena as they both mourn Bonnie's death.
In Monster's Ball, Damon showed at Elena's school as she has been avoiding him to accept her invitation to the Whitmore Historical Ball. It's the one time of year that the college's entire collection of artifacts is put on display and people dress up as historical figures. Back in Mystic Falls, Damon told Jeremy that he wants to work with Silas. Since Silas wants to die to reunite with his own true love, why not use his death to reunite Bonnie with Elena. Nature loves a balance. When Silas takes the cure and becomes a witch, he might be able to do a spell that swaps his life for Bonnie's. Silas can't be trusted, and there are consequences when you abuse magic (especially when you're resurrecting someone). She said not to do this, but Jeremy told Damon that she was in.
During Damon's conversation with Silas, we learned that Silas saw Qetsiyah buying a Cleopatra costume, so she'd be at the costume ball as well. And Silas needed Damon to kill Stefan. At the costume ball, Elena and Damon were dressed as Anne Boleyn and and Henry VIII. Damon wanted to dance but Elena wasn't in the mood. She said it's not her fault that Bonnie died but it is her fault that she didn't figure it out sooner. She's not gonna let Megan's death fall through the cracks, too. Qetsiyah approached Stefan at the bar and wanted to buy him an "I'm sorry" drink. It would take a keg, Damon said, and led Stefan away. Stefan critiqued Damon as a wing man -- "Trust me, the last guy to hit on her is still paying for it," Damon responded -- and then Silas was there. "Hello, me." Damon snapped Stefan's neck. When Stefan is "dead," the link between them is gone and Silas has his psychic powers back. Silas was going to pose as Stefan.
Later, Stefan came to. He was pumped with vervain, so Damon could easily snap his neck again after he explained he was doing this to get Bonnie back for Elena. When Silas had a headache again, Stefan tricked Damon and snapped his neck. "How's it feel, brother?" Damon and Elena found Silas. Elena thought it was good that Silas is out of commission. But Damon knew it wasn't. Because they needed him to get Bonnie back.
Back at Salvatore Mansion, a desiccated Silas was on the couch as Elena and Damon talked. The only way for Silas to trade his life for Bonnie's is if he's a witch. The only way to become a witch is to have the cure. Someone was knocking on the door and it turned out to be Katherine. Katherine thought she was there so they could show her that she'd eluded death yet again. They finally did something right for once. How did it feel? "Thrilling," Damon said. And she figured it out. Damon bit her neck and she begged him: She said Silas would need all of her blood and she didn't want to die. "Goodbye, Katherine," he said, and he held her head down to Silas' mouth. Silas' hand came up to her head. Katherine dropped to the floor. But then Damon heard something. Her heartbeat. She awoke. "Am I in hell?" she asked.
In Handle with Care, when Damon and Elena are snuggling on the couch and having a sweet moment, Silas comes in ruins their blissful moment to discuss their plans for his death. Elena is having trouble trusting Silas' word that he will bring Bonnie back before he departs the mortal world for good, so he snarkily offers to pinky swear. Everyone is looking for the anchor now. Silas wants to die and find peace. Silas then refuses to allow Elena to come along when she looks like his true love and doesn't want to stare at her all day. As Elena gets annoyed, Silas uses his magic to shoot the crossbow at Elena's leg. This upsets Damon and he hurries to help her.
Damon, Silas and Jeremy take a road trip to New Jersey only to end up at a huge warehouse full of junk that holds the anchor, so they begin the search for the anchor. When Tessa lures Elena to the cabin in order to use her as leverage against Damon. She wants Damon to kill Silas before the sun sets, or she will kill Elena. Damon tells Jeremy that the deal is off and Bonnie isn't returning because he has to kill Silas to save Elena. Damon walks back into the warehouse and is greeted by a Traveler speaking a foreign language, and is soon ganged up on. They manage to neutralize his daylight ring (reminiscent of the witches in Mystic Falls), and say that they don't want Silas dead yet...right before Damon kills them both. At the warehouse, Amara is stumbling around murmuring to herself, “leave me alone.” Damon finds her.Damon and Jeremy are throwing a pity party for themselves due to their failure to bring Bonnie back. They let Elena in on the big twist for the episode though, and Damon introduces Elena to Amara.
In Death and the Maiden, after Silas is no longer interested to bring Bonnie back, Damon turns to Qetsiyah for help.He asks Qetsiyah to perform a spell which can make Bonnie the new anchor to the other side.She agrees to help them since with that switch, Amara will die and the Other Side will remain existent so she can be there with Silas for the rest of time. To perform the spell she needs blood from all three doppelgängers, Elena, Katherine and Amara to which Damon sarcastically replies "You want Doppelgänger blood? I've got Doppelgängers coming out of my ears."
During the spell, Silas intervenes and tries to stop it. The power goes out and in the chaos, Stefan who just wants revenge against Silas after what he has done to him kidnaps Amara while Silas and Qetsiyah start fighting. Damon comes in and catches up with Elena on where is Amara gone and she tells him to go find Stefan because he wasn't thinking right. Silas might have put him in that safe but they were the ones who were supposed to get him out of it. Damon reaches the scene and finds Amara dying. He does everything he can to keep her alive for a few more minutes so that Qetsiyah is able to complete the spell. They are finally successful as Qetsiyah completes the spell in time and Bonnie becomes the new anchor. At the end of the episode, Stefan admits to Damon and Elena that he wanted it to be them who would find him and get him out of that safe.
In Dead Man on Campus, Elena calls Damon to invite him to her party and also suggests to invite Stefan. Then Damon tries to talk to Stefan, but he's freaking out, reliving his repeated drowning. Damon can tell something is wrong, but Stefan won't tell him.
Later, at Elena's request, Damon decides to get answers from Dr. Maxwell. In Maxfield's lab, Damon pokes through his lab samples. He explains to Maxfield that he's going to inject him with a disease and he'll heal him with his vampire blood if Maxfield talks. Damon thinks that it’s sick that Dr. Maxwell turns innocent kids into vampires just for an experiment. Damon gets another tube of some kind of virus, it’s “rabies” into Maxwell. Then Maxfield explains he was trying to create a new kind of vampire that doesn't feed on human blood but instead he feeds on vampire blood. Damon tells Elena about Jesse feeding on vampires, and she makes him promise not to kill Maxfield. In the lab, Damon slices his wrist to heal Maxfield of the various diseases he's injected him with, but Jesse storms in, wanting answers from Maxfield. He sees Damon's bleeding wrist and attacks him. Damon isn't worried, since he's a much older vampire than Jesse, but he soon finds out the usual strength-age rules don't apply. Jesse tackles him out a door and into the hallway. Jesse overpowers Damon and begins to feed on him when Elena finds them. With Jesse attached to his neck, Damon tells her Jesse's about to rip his head off. Elena grabs a shard of the broken door and stakes Jesse, killing him, just as Caroline runs up in time to see it. Elena feels awful, but Damon tells Caroline she had no choice and leaves to deal with Maxfield.
Back in the lab, Damon cleans up as Maxfield secretly works his way free from his restraints. Damon plans to compel the whole thing out of Maxfield's head. When he sees a bag of labeled blood in the fridge, the number jars his memory. Damon remembers his own number from trials 60 years ago. Maxfield realizes Damon was an Augustine vampire, too. Maxfield breaks free and Damon is unconcerned as he runs to the opposite side of the lab. But then Maxfield hits his "emergency procedures" button and atomized vervain fills the room, dropping Damon. Damon wakes up in a cell that is hauntingly familiar. His initials are scratched into the wall and memories of his time in captivity, being tortured, come rushing back.
In The Cell, Damon wakes up in a cell with Wes Maxfield injecting him with vervain. He tells Damon that because he killed their test subject last night (Jesse), Damon's going to take his place. Maxfield tells Damon that after training Jesse to crave vampire blood, he's ready to take his research to the next level. Later Wes captures Elena too in a cell next to Damon. She wakes up and Damon confesses he's been there before and tells her about Whitmore's torture, including cutting up pieces of them every day. He was there for about five years. He made a friend, Enzo, a soldier in Europe during WWII, who was also a vampire. Elena tells Damon that her dad worked with Whitmore and was an Augustine. She doesn't want to believe he'd be part of a place that would cut Damon's eyes out and breaks down. Damon confronts her and promises her that he'll get her out of there.
Damon continues to tell her about his past and also tells Elena that Enzo's friendship is what kept him alive and holding onto his humanity. But the craziest part is that he also reveals he never told anyone, including Stefan, what happened during his Augustine imprisonment, so Stefan won't know where to look for them if he even notices that they're both missing. Damon explains how he escaped. They let the vampires out once a year for the Augustine's New Year's Eve party to show them off. They were weak from vervain and captivity. Whitmore demonstrates vampire blood's healing powers, using Mrs. Fell as a volunteer. She drinks vampire blood to heal her hand after he cuts it. Enzo comes up with a plan, suggesting one of them drink both of their daily rations of blood for a year so that when they're let out next New Year's Eve, one of them will have the strength to fight. They play rock paper scissors and Damon wins. Elena wants to know what happened, but Damon is not forthcoming with the details, saying only that it wasn't pretty. Elena convinces him to tell her by saying that she loves him and doesn't care what he did to escape. Damon finally tells Elena his shameful secret: he left Enzo to die during his escape. After massacring the party on New Years Eve and knocking over a candle, he tried to break the cage to free Enzo but the bars were vervained and he couldn't get him out. Damon flipped his humanity switch so he would stop caring about Enzo, and left him to die in the ensuing fire. Elena was horrified that Damon left Enzo.
Aaron comes down to the cells in the basement with his gun. He accuses Elena of killing Megan and possibly of killing his parents. Damon stops him, and says it was him. Damon explains that with Enzo dead, he had to carry out his revenge plan himself. He planned to kill all the Whitmores in a generation, except one, then let him grow up and start a family, and then kill all of them except one, and so on. Elena is disgusted and asks when the last one was. A few months ago, Sarah in Charleston. It was a weekend trip. Elena realizes they were together then. Aaron shoots Damon leaving Elena upset. When Damon wakes up, he finds Elena's cell empty realizing that Wes has taken her.
In Fifty Shades of Grayson, Damon uses the last of his remaining strength to punch at the stone wall until a chunk falls out. He reaches through the grate for the bullet Aaron dropped when he came down. Damon puts the bullet in the lock and bashes at it with the rock, then kicks the door until it opens.
Damon visits Stefan and tells him they have to go get Elena, but he doesn't know where she is, so they need leverage. Damon and Stefan find Aaron Whitmore and Damon tells Aaron to call his uncle to get Elena back, or Wes gets to try to reattach Aaron's arms. Aaron calls Wes and he agrees to meet them in his classroom. The Salvatores arrive with Aaron at Wes's classroom and find Enzo waiting for them. Damon tries to skip over introductions, but Enzo is eager to tell him how he survived the fire that Damon left him to die in. He reveals that one of the scientist spared him. Damon is ready to get on with killing Aaron, but Aaron mentions some files Wes gave him that are in his dorm room. Enzo tells Damon to stay with him as Stefan goes with Wes.
Back in the classroom, Damon continues refusing to react to Enzo's guilt trips. Enzo mentions that Wes poisoned him and he has to return for the antidote. Damon suggests they work together to save both Enzo and Elena. Instead, Enzo tells him that Wes said he couldn't return until Damon was dead. Then Enzo throws him out the window. Enzo keeps trying to come after Damon, but Damon refuses to fight him. Enzo is too weak from the poison to really attack. Damon tries to get him to tell him where Elena is, but Enzo desiccates before he can talk. Enzo wakes up in a lab. Damon tells him he injected him with everything labeled antidote. Damon reaches inside Enzo's chest and tells him he had to flip off his humanity to leave him. Enzo tells Damon that he was the most important person in his life and he ruined him and that he is just a monster and always will be.
Later at the Salvatore house, Damon finds Elena reading through her dad's journal. She found a reference to Megan in her dad's journal. He cured her from a congenital heart defect, which is why Megan had a picture of Grayson Gilbert in her phone. Damon isn't surprised that Elena is able to find the one positive thing out of all the torture. He doesn't understand how Elena can keep looking past all the terrible things that he has done. She says she loves him and accepts him and because she chose him. Damon replies that now he is choosing and he chooses to let her go. Elena begs him not to run away because she has done horrible things too and that she won't judge him after finding out that he was tortured for 5 years. He shouts at her to stop defending him. Damon confesses that he can't change who he is but he refuses to change Elena and leaves. Elena is devastated and starts crying.
In 500 Years of Solitude, Damon is having a tough time dealing with his break up. Jeremy and Matt find a drunk and depressed Damon at the Grill. Both are shocked as to why Damon would dump Elena. Later in the Boarding house, Damon pours Matt and Jeremy shots for all the horrible things Katherine has done to them through the years. Elena,Caroline and Bonnie also arrive and join the toast game. Stefan comes downstairs to tell everyone they're being insensitive, but Damon warns him not to let the fact she's an Elena lookalike could the fact she's a manipulative psycho. Stefan mentions her seducing both him and Damon, turning them into vampires and starting a war with the town that got them killed. But he goes on to say that before that she was just a frightened girl shunned by her family, and she became a survivor, so that's what he'll drink to. Damon mocks Stefan for being so easy on her after one night of passion. Their moment is interrupted by Nadia who explains she has found a way to save her mother. Damon forbids anyone to help, which Nadia expected, which is why she buried Matt in the safe somewhere on the property, without his ring.
When Elena and Stefan volunteer to save Katherine in exchange for Matt, Damon decides to spend his time torturing Katherine by controlling her mind. Damon picks up a pillow to smother an unconscious Katherine. But Liz Forbes comes in and stops him. "Every awful thing I've done is linked to her. She taught me how to kill, how to enjoy it. She ruined me and I can't take any of that back," he says. "Look at how much control she still has over you, Damon. Prove her wrong," Liz says. Damon continues to toy with Katherine but is stopped by Nadia by snapping his neck. Damon wakes up on the floor but stays still and listens as Katherine tells Nadia that she's been selfish her whole life and just wants to do the right thing for once. She asks Nadia to let her go. Damon is surprised by Katherine's act of selflessness.
After Stefan says his goodbye to Katherine he and Damon talk about their eventful days. Damon understands why Stefan was being nice to Katherine. She helped pull Stefan out of a dark place. Stefan tells him to fix whatever is going on with him and Elena. Stefan tells Damon that she is the best thing that has ever happened to him and Damon doesn't deny it and confesses that he can't live without her but he doesn't think he's any better than Katherine and Elena will be better off without him. He's trying to be selfless. Stefan gives him a look and convinces him to get her back. Damon jokes that when he gets Elena back and the whole universe freaks out for keeping the doppelgängers apart, Stefan should remember he's the one who talked Damon out of doing the right thing for all mankind.
Later, everyone gathers in front of the fire, going through bourbon. Jeremy hears Alaric. "Where the hell have you been? I thought you bailed on us to go find peace or something," Jeremy says. Alaric replies "Do you honestly think I'd leave Damon in charge and never look back?" Jeremy translates to Damon that Alaric says you are a dick. Damon's face lightens up as he realized Rick is here too and they toast.
In The Devil Inside, Damon has buried Katherine's body and won’t tell Stefan where. Nadia is also there telling the Salvatore brothers she wants her mother's corpse. Damon tells her she’s out of luck. Nadia gets mad and tries to make Damon give it to her but he quickly tells her no. At the grill, Stefan is trying to talk Damon into giving Katherine’s body to Nadia. Stefan is also giving him a pep talk about Elena. Caroline shows up, Damon starts calling her out on her hate for him.
Enzo is waiting for Damon at the Salvatore mansion, with a huge body bag. Inside is Aaron - still alive. He did some research into Damon's revenge plot and thought that he would want to finish it off. Damon is trying to mend his ways and get back with Elena, so when Aaron wakes up, Damon snaps Enzo's neck. “I didn't see that one coming,” remarks Aaron. Damon rips off his vervain watch and compels Aaron to leave town immediately. Then he is off to the party. Elena makes it to the party and sees Damon and she falls into his arms, but Mia completes the ceremony, and in the comforting hug, Elena becomes Katherine for good. Damon makes an impassioned speech for them getting back together - that he knows he screwed up and gave himself too much credit for thinking he would change her and her not enough for thinking she couldn't change him. Katherine is having none of that. “I'm glad that I make you a better person, but that is too much pressure. I can't be the only thing you live for.” Damon is absolutely crushed when Katherine/Elena says goodbye.
Aaron is on his way out of town, just as Damon compelled him to do. He stops when he sees a man laying in the road, and gets out to help. The man sits up - it is Enzo. Damon appears behind Aaron and informs him that he is here because of Elena. “She thinks I am a monster. She's right.” Then he brutally feasts on Aaron's blood.
In Total Eclipse of the Heart, Damon is first seen in Salvatores living room, when he is sleeping on the couch. Stefan comes to him and asks about this mess he has done to the room and about Aaron's corpse in his car. Damon and Enzo are telling Stefan that they are going after whole Augustine institution, to get the full revenge on them. Stefan says to Damon that he is better than this, but Damon says that he is better like this.
Enzo and him have captured Diane, who works for the Augustine and compel her to talk all she knows about Wes Maxfield. When they get all the information from her they kill her and are trying to find Wes on their own. Damon then seeks out Bonnie and Jeremy, so Bonnie will find someone to do the locator spell or Enzo is going to kill Jeremy. While Jeremy says that Damon is not going to hurt him, because Elena would never forgive him, Damon proves him wrong and says that Elena has already given up on him and takes Jeremy hostage while Bonnie is trying to figure out how get some witch for locator spell to save Jeremy. When the witch seems to fail, he tells Enzo to give them more motivation when it is taking too long to find Wes. When Katherine and Stefan find Jeremy, Stefan and Enzo then fight each other. Damon then appears and tells Enzo he found Wes' location as Damon is about to walk away, Stefan tells Damon "Don't bother coming back" and Damon replies "I wasn't planning on it."
Damon leaves with Enzo to kill Wes, with Stefan looking upset about Damon's bad choice to leave with Enzo. But they then walk straight into a trap and are ambushed by travelers who are attacking them. While the Travellers are holding Damon and Enzo down, Wes infects Damon, turning him into an Augustine Vampire. Damon then tells Enzo that if what Wes injected him with what he thinks he did they're going to have a problem. At the end of the episode, Damon finds another test subject vampire who is bleeding and then begins to feel his body elevate at the smell and sight of his blood. Damon then violently feeds on the test subject to the point where Damon rips his head off. Damon then turns to a shocked Enzo seeing they have a problem then stares at Damon who stares menacingly back at him in shock of what has happened to him. The episode ends, with Damon looking at the camera with him covered in blood.
In No Exit, Enzo and Damon just got done killing a couple at a Farm house. Enzo is keeping tabs on Damon, tracking his eating habits. Enzo is making their victims into vampires so Damon can feed. The farmer tells them his wife left him for a pharmacist, then Damon kills him. The Travelers appear and trap the pair in the house. Wes is also there, he wants to run another test, trapping him in there with his only source of food, his best friend. Later, Damon and Enzo are still stuck in the farmhouse. Damon is getting antsy. Enzo tells him “calmer heads will always prevail”. He also tells them he should call one of the Mystic Falls gang for help. Damon tells him he won’t feed on him and he'll find another way. Enzo ties him up. He tells Damon that Damon's problem is that he runs. Enzo tells him that he’s calling for backup. Damon gets mad. Enzo calls Stefan’s phone and tells her what’s going on. Katherine tells him to text her the directions and they would be there soon. Wes shoots Enzo so Damon can smell his blood. Wes wants to know how strong and desperate Damon will get for blood. Damon starts feeding from Enzo whom is begging for him to stop. Damon starts choking. The Travelers did a spell to make Enzo's blood like acid. Wes tells Enzo he can come with them or stay with Damon. Damon tells him to go but Enzo is hesitant. He leaves with Wes.
Katherine shows up, Damon is begging her not to come in. Damon asks them to leave but Stefan tells him he's not leaving. Stefan tells Damon he isn’t afraid of him when he goes to attack him. Katherine walks inside saying “neither am I” but then gets stuck in the house. Katherine even cuts her hand, Damon is trying so hard not to hurt her. Katherine keeps pushing him. Damon starts feeding from her and Stefan tries to get Damon to stop. Stefan picks up a piece of glass and cuts his arm. Damon goes to feed off Stefan then Stefan snaps his neck. Stefan is talking to Damon whom is strapped to a chair in the basement. Damon tells him one day he will kill him. Stefan tells Damon he isn’t going to give up on him and he never will. Damon brings up Elena, he knows that Elena has given up on him and that “she” wanted to kill him.
In Gone Girl, Stefan fills Damon in on Katherine is in Elena's body. "She's brilliant," is all Damon has to say. Stefan assures him to not to worry and that he has a plan. Later, Stefan feeds Damon 4 ounces of his blood, figuring that some every few hours will stave off his hunger. Stefan decides to call Katherine feeling that she won't say no to him like she has shrugged of everyone's attempt to meet her but Katherine instead calls Damon, wanting to talk. He invites her by the house. When she hangs up, Katherine assesses that Damon would never put Elena in harms way again after nearly killing her so he must have known that its Katherine. Stefan and Damon come to the same conclusion: Katherine knows that they know about her being inside Elena's body. Caroline and Stefan try to figure what to do next and then Damon suggests a locator spell.
Later, Tyler is guarding Damon and sits outside the cellar. Damon asks him what he's still doing in Mystic Falls with his whole family dead. He thinks Tyler is convinced there's still a chance with Caroline. Damon taunts him about Caroline until Tyler comes close enough and then Damon bites him and breaks free running to find Wes. Damon reaches Wes' lab and threatens him to make him a cure for the ripper virus but Wes refuses and Damon ends up killing him.
Damon reaches in time at the Salvatore house when everyone is planning to kill Katherine for good. Katherine taunts him by saying "But I never got to say what I needed to say to you. I’m sorry. You blame me for who you are, and I’m sorry. I’m sorry I turned you. I’m sorry I drove you to abandon the war. I'm sorry that you didn't get to die as a forgotten nobody on a bloody battlefield, that your father didn't get to live another day to be disgraced by you. Damon, I'm sorry that I gave your life passion, purpose, drive, desire. I'm sorry that you are who you are, because I'm the one who taught you how to love." Damon simply ignores her and adds ""I'll see you in hell, Katherine." Stefan then daggers Katherine with the Traveler's Blade killing her permanently.
Later, Damon along with Stefan is waiting for Elena to wake up. Damon tells Stefan that he plans on to tell Elena everything he did in her absence and is ready to face the consequences. He's determined not to be another Katherine and spend his whole life running. Elena then wakes up and Damon smiles at her. Elena greets Damon happily and assures him that its really her. It is then revealed that Katherine injected Elena's body with the enhanced Ripper Compound that Wes had made making Elena a vampire ripper just like Damon.
In While You Were Sleeping, Damon is being fed blood and watched by Jeremy and Matt. They taunt him about how Elena doesn't know Damon killed Aaron Whitmore but he warns them he will be the one to tell her. Elena is also locked in her dorm room because of the ripper virus and calls Damon after Stefan informs her of the ripper situation. They both are happy to hear each other. They are flirting when Elena asks him how Katherine broke his heart. He shrugs it off saying he doesn't remember. She then says "The last thing I remember I was running into your arms and I felt so safe," and he replies "It was all downhill from there." Elena then tells him how she wanted to fight for him and still want to, Damon joyfully replies "Oh Elena..the second we are cured of this and don't want to rip each other's heads off, I am going to hunt you down and give you the most mind-blowing night of your life." Elena excitedly says that she can schedule him in.
The werewolf venom insides Elena makes her hallucinate stuff which leaves her disturbed, she calls Damon again and ask him to distract her. He mischievously asks what is she wearing making Elena blush. He then tells her about Klaus and Caroline. Elena asks why they don't just hunt down Wes for the antidote and Damon confesses he killed him. Elena is upset saying that he was the only family that Aaron has. Elena's hallucinations start going worse and makes her believe she killed Aaron. Elena calls Damon in a panic, she can't tell what's real anymore. She tells Damon she thinks she killed Aaron. Damon promises to tell her everything, but says now isn't a good time. She freaks out, yelling that everyone is lying to her. Damon gets worried and manages to free himself from the cell while Elena threatens Liv to drop the seal and then goes out of the campus.
Damon finds a disturbed Elena and tries to help her. He gives her Stefan's blood to drink. "She won, Katherine won," Elena said. She rants about nearly killing Liv and killing Aaron Whitmore. Finally, Damon tells her she didn't kill Aaron but he did. Damon then reveals why he did, because the only person he believed could change him from being a cold blooded killer to a better person instead told him that he could never change. He waits for her to say something, but she sees Enzo there with the antidotes.
Back at the Salvatore Mansion, Damon offers Elena a drink to which she declines and then goes says how Damon should have noticed that it was Katherine not Elena. If he had, Aaron would still be alive, there'd be no virus. Damon points out she's blaming Katherine for his mistakes and making excuses for him. Damon says he killed Aaron because she broke his heart and this is how much control she has over him while Elena says that even after all this she is still here and this is how much control he has over her. He calls their relationship toxic and Elena confesses how she has to compromise her morals again to make excuses for him and she does it because she loves him. He tells her to stop loving him, but she yells that she can't. Damon replies that this is the problem and they mutually decide to end their relationship. However they both gaze at each other longingly and Damon then kisses Elena to which she reciprocates. They begin to make out and Elena rips his shirt. They are then in Damon's bed and end up having hot passionate break up sex.
In Rescue Me, Elena and Damon stay woken up for 3 hours without saying anything after their night together, post break up. Elena's phone buzzes to remind her to go to Jeremy's parent-teacher conference. She starts putting on her clothes while Damon greets her. Elena says they're still bad for each other and still broken up and last night was a mistake. "Maybe we should keep making mistakes," Damon replies. She leaves, despite his offer of a naked breakfast. Damon heads to the Grill to drown his morning sorrow in booze. He seeks relationship advice from Tyler and Matt and mentions that Caroline is off doing something with Stefan, although he taunts Tyler by assuring him they're just friends. Later he sees Bonnie's new witch friend Liv hanging with Jeremy.
Damon then visits Jeremy's school to attend his parent teacher conference and surprises Elena. Waiting for the teacher at school, Damon flirts with Elena, who tries to keep him on task. Damon mentions seeing Jeremy with Liv and a bottle of booze this morning at the Grill. Elena is sure Jeremy's not a cheater. Then the teacher comes in and complains about Jeremy saying "Jeremy's missed 11 days of school, he's started three fights and he's been caught cheating in math class twice." When the teacher realizes that Damon and Elena have broken up she tells them that Jeremy needs a stable living situation.
After talking with his teacher, Damon points out that Elena is making excuses for Jeremy, just like she always does with people she loves. She thinks he wants to talk about last night. He corners her near the locker and admits he doesn't know what to say, but just wants to take her into one of the classrooms and kiss every square inch of her body while people who drive minivans listen and wish they were them but then adds that it is probably a bad idea. Elena tries hard to breathe and with great difficulty whispers right. Damon leaves by saying see you in class while Elena is left completely shaken. Later in chemistry presentation, Damon wakes a lost Elena. Unknown to him she was daydreaming making out with him and frustrated with their sexual tension she leaves the class room. Damon then finds Elena with Liv who is about to kill her. Damon saves Elena and starts torturing Liv for information. Liv doesn't cooperate and he is about to kill her but Jeremy stops him. He convinces Damon and Elena that Liv will help them protect Elena from the travelers.
At the Salvatore house, Jeremy tells Elena and Damon that he has decided to live with Matt and Tyler leaving both of them upset. Later, Elena is packing her stuff and Damon asks her to not leave but she says that when they are together they do bad things for each other and she can't live with that. Damon offers to drive her to Whitmore but Elena confesses that if he does that then she won't be able to control herself around him and thus they are gonna end up back here. Damon then slowly walks up to Elena, then she believes he is going to kiss her. Instead Damon then shushes her and does the selfless/right thing, he takes his hands around her neck then slowly kisses her forehead and tells her Travel safe. Elena then seems shocked by Damon's act of selflessness as he walks away, she then seems upset that he finally let her go.
In Resident Evil, Damon is playing pool with Enzo to distract himself from Elena. Enzo tries to understand how things are going with Damon and Elena. Damon turns things around on Enzo and asks about his missing girlfriend, Maggie, who the Travelers were supposed to help him find before they all attempted suicide. They then get a call from Caroline who informs him about the weird visions Stefan and Elena are having about each other. He asks her to bring a witch and come to the house. When Caroline and Elena arrive at the house, Damon and Elena have an awkward post break up reunion. Caroline and Enzo leave them alone and eavesdrop their conversation from another room. Elena and Damon try to act normal but when she suggests to be friends, Damon cringes at the idea. Damon then changes the subject to her visions about Stefan. Soon they are interrupted by Liv's brother Luke who happens to be a witch as well.
Luke tells them about Travler's leader Markos and how he is back from the other side. He suggests the visions are the Travelers drawing Stefan and Elena to them, but they need more clues. Later that night, Damon drinks outside, "listening to the universe laugh at me," he tells Elena. "We were doomed from the beginning, Elena. We were always going to end up here." She assures him the universe doesn't control anything and the dreams are not real. She then has another vision in which she sees the house address and hence announces where to find Markos. Damon and Enzo go in search of Markos and he explains to them that the doppelgänger prophecy is not true and the reason why doppelgängers are drawn together is because of a spell that he casted 1500 years ago because travelers needed their blood.
Markos then takes Damon to a walk and reveals the history of travelers that when Silas and Qetsiyah created the immortality spell, it created a schism in the Traveler community and gave rise to the witches, who tried to keep the Travelers scattered because they're more powerful together. The witches put a curse on them that kept them from settling down together as a tribe. Doppelgänger blood can fix it. He tells Damon they don't want to hurt him and he'll end the visions. Damon then watches several travelers coming forward who have passengered themselves inside residents of Mystic Falls. All the travelers together finish the spell and the visions stops.
Damon returns to his room and finds Elena waiting. She tells him that the visions were indeed a fantasy but they weren't real and even though Damon and her are messy and complicated they are real. But Damon replies they are still bad for each other. Elena says she still wants him in her life but Damon becomes flustered and tells Elena that he doesn't want anything to do with her as he can't be friends with her. Elena then leaves the room while trying to control her tears.
In Man on Fire, Damon is focusing on dealing with the Travelers situation. He drops in on Matt and Jeremy at Tyler's house to take the Traveler knife but unfortunately they can't find it and neither have they heard from Tyler. Damon becomes angry and calls Enzo asking him to go on field trip in search of the travelers but Enzo refuses as he has some other plans. However later he calls Damon and asks him to check Stefan's journals from November 8, 1960. Damon tells him Stefan burned them all. Enzo then reveals how he thinks Stefan is responsible for killing his one true love, Maggie and that he has Stefan and Elena captured for revenge. Damon leaves a message for Caroline while meeting with her mother to get the report on Maggie's death. Damon looks at the crime scene photos and recognizes it. "Stefan was right, he didn't kill Enzo's girl. I did," Damon tells Liz.
He then hurries to Whitmore and finds Enzo with Stefan and Elena tied with vervain ropes. He reveals to them that on November 8, 1960, he got a message at the house that a woman wanted to interview him. He didn't know she was Enzo's Maggie. She wanted revenge from him for leaving Enzo behind in the fire but she didn't stood a chance against Damon. Damon had killed her and made it look like Stefan did it because of his grudge of Stefan not coming to get him the five years he was in Augustine captivity. Damon asks Enzo to resolve this among themselves and not to include others. Enzo confesses he can't hate Damon because then he has nothing left. He realizes there is another option and switches off his humanity.
No humanity Enzo is in a joyful mood. Damon suggests Enzo to leave with him and slips Stefan a shard of glass to free himself. Enzo bites Liv and attacks Damon on his neck with a broken glass. Stefan breaks free and pulls Enzo off, but Enzo gets free and grabs Elena and runs. Stefan stays to feed his blood to mortally wounded Liv and Damon goes after Elena. He leaves Enzo a message begging him not to kill Elena. He then finds an unconscious Elena outside Whitmore College and carries her to her dorm room. He lays her on the bed and caresses her face. As she starts gaining conscious he vamps speed out before she can see him.
Later at the Salvatore house, Damon tells Stefan that he will find Enzo and fix all of this. Stefan hides the fact that Enzo is dead and tells him that what happened with Enzo wasn't his fault. Damon talks about how Enzo kept him sane in captivity, reminding him he was lucky to have any family at all. Every time Damon wanted to give up on Stefan, Enzo urged him not to lose faith in his brother and hence Damon owes him. Enzo's ghost watches over the brothers as they share a drink. "It's too late to make amends, Damon. You know me, never let go of a good vendetta. And this one is just getting started," Enzo says.
In What Lies Beneath, Damon is seeking Luke's help to track Enzo who is unable to find anything. Damon tells Stefan a vampire with his humanity switch flipped who wants him dead is worth finding, but Stefan suggests Enzo has a witch performing a cloaking spell on him and doesn't want to be found. Tyler comes in to announce the problem of the week. After some conferring, they expect the Travelers will be coming for Stefan and Elena today to break the witches' curse so they can settle in Mystic Falls. Damon orders Tyler to commune with the Traveler inside him to find Markos, he tells Luke to perform an anti-locator spell to hide doppelgängers Stefan and Elena from the Travelers and he tells Stefan that they're going to take their ex-girlfriend on a secret trip to keep her and Stefan safe.
Damon, Stefan, Elena and Caroline decide to hide in Caroline's father's remote cabin from the travelers. They take Luke along with them so that he is able to perform an anti-locator spell which will hide them from the travelers. While Elena is unpacking her stuff, Damon visits her and they talk about the cabin and Caroline's father. Damon then mentions how he should be avoiding her and Elena asks him if that is what he still wants. Damon replies "Yes. No. I don't know." Elena offers him an out and Damon asks if she is kicking him out. She repeats his words saying "Yes. No. I don't know." They share a flirtatious smile and the conversation soon becomes awkward when Damon mentions Enzo. Elena is feeling guilty about lying to Damon about Enzo's death by the hands of Stefan and leaves making an excuse.
Later, Damon preps cocktails while Caroline makes clues for charades. The theme is "secrets people think they're getting away with," and she thinks "Team Stelena" will do fine. He picks up on her "judgy little hinty voice." She thinks they're being secretive. Damon thinks she got cagey when he brought up Enzo, but Caroline thinks it's more about the two of them. In the evening, the gang is playing charade and there is still no sign of any secret. Then Damon suggests to play "Never have I ever." It goes around until Caroline says "Never have I ever kissed a Salvatore brother -- today." Then Damon says "Never have I lied about where Enzo is." Stefan and Elena are silent and the evening comes to a screeching halt. Elena gets up and leaves for bed.
While Elena is taking a bath, a ghost Enzo who now has the power of touching things in the real world tries to drown her for revenge. When she's able to come up for air, she screams for Damon. He comes to rescue her and wraps a towel around her. He tries to calm her down while Elena panics about what happened. Damon then wonders why a ghost would wanna attack Elena. She finally admits the truth about Enzo's death. Damon joins Stefan and Caroline and they figure out that drowning Elena was just a distraction, Enzo figured out a way to kill them all. He has taken Luke somewhere making it possible for the travelers to track them.
Damon asks Stefan what he thought he'd do when he found out Enzo was dead. "Hate me," Stefan says. Before Damon could answer him, they hear a voice from the shed and find a barely alive Luke inside. Damon spells the gas just before Enzo yanks down a light to ignite it. The cabin is quickly engulfed in flames. Enzo manages to trap both Stefan and Damon inside the shed by attacking them. Damon asks Stefan to run with Luke while he manages to convince Enzo to let go of his revenge by promising him that he will bring him back. Damon then runs away from the shed. Back at the Forbes cabin, Stefan starts to apologize to Damon, but Damon punches him. "I had to do that, for Enzo. But it's the last time you'll hear about it from me," Damon says.
Later, Damon is packing up the car in order to move to a new location when Elena approaches him. He tries to brush her off and warns her to hurry as the travelers must be coming. She apologizes for keeping Enzo's death a secret and he says he doesn't care about her lies. She is confused and asks him why is he behaving like this. He then confesses that he knew she lied because she was afraid that he will spiral out of control again but he didn't this time despite every nerve in his body wanting him to because for her. Elena smiles slightly to herself and playfully asks if he is still mad at her. He further confuses her when he says "Of course I'm still mad at you because being around you drives me nuts, and not being around you drives me nuts." They stare at each other for a while when Damon finally runs towards her and kisses her passionately. Elena whispers what was that for and he mentions how he had a really bad day and he needed it. He goes inside the cabin while Elena has a brief moment to enjoy the glow when suddenly the travelers arrive there paralyzing her brain and Markos grabs her from behind.
In Promised Land, it has been four days since the travelers took Stefan and Elena and Damon has been desperately searching for them. He is torturing a Traveler inside a guy named Sykes. He asks him where Markos is as the Travelers want to break the witch curse so they can settle, it also reverses the witch's spell that created vampires and they all die. Damon ungags the Traveler long enough for him to say there's nothing they can do to stop Markos. Later, he gets a call from Stefan who informs him that he and Elena have managed to free themselves from the travelers but don't know where they are. When Stefan tells him that he has Elena hunting squirrels, Damon jokes that Elena will shoot Stefan's eyes. Damon tells him that he will find and kill Markos and asks him to have both him and Elena return home safely.
Damon gets off the phone and gets a knife in the chest from ghost Enzo, reminding Damon to keep his promise to bring him back. Damon points out to Bonnie that he's busy with Markos, so he suggests she get Liv to include Enzo in her spell to save Bonnie from the collapse of the Other Side. Bonnie doesn't get a chance to tell her there is no such thing because Damon leaves with Jeremy to get the real bodies of the travelers which are lying inside the caves. He along with Matt and Jeremy return with the unconscious bodies of the travelers and start placing them around the boarding house. When Damon is dismissive of passengered Tyler, chained up in the basement, Caroline accuses him of just being grumpy over Elena. Caroline warns him to not to go against the passenger inside Tyler until she figures out how to save Tyler.
When Markos finds Damon's note in the caves telling to contact him for missing wannabee witches a.k.a the Travelers, he decides to visit Damon at the boarding house. At the house, Markos seems unconcerned about the fates of his people. He stabs one in the neck to prove his point, telling Damon he doesn't care if they never get back in their original bodies. He explains that Travelers are everywhere and are willing to die for a better life. Markos also tells that after they perform the spell and it's affects ripples out from Mystic Falls, only Traveler magic will remain all over world. While they are talking, Julian whispers to Damon from the basement that Markos doesn't know he's there and Damon should use that. Damon makes an excuse to go downstairs and slip Julian a key to free himself.
Julian finally manages to attack Markos but it's too late as the Travelers have already started the spell and hence his fangs start disappearing and Damon's ring stops working. As the spell is being performed, the travelers inside the Salvatore house start waking up. Damon suddenly gets a bullet wound in his chest, exactly similar to the one he got when he died as a human. Markos explains that as the spell will unravel spirit magic, vampires will continue to die as they were supposed to die as humans. Damon and Julian start running away to the door to run away from Mystic Falls. Before Damon leaves, he takes one last look at the place he has called home for over 100 years and is clearly upset. Damon makes it to the road, where Jeremy picks him up.
Elena, Damon, Stefan, Bonnie and Caroline plan to meet in Whitmore and travel far away so that they are unaffected from the traveler's spell. When Damon reaches Whitmore, Elena rushes to him and kisses him passionately. When he asks what was that for, she repeats his words from their last kiss, "I had a really crappy day and I needed it". She also confesses that she thought she would never see him again and couldn't think of a worse way to die. They are both enjoying their little happiness when Stefan says that he will wait for Caroline and Bonnie. Damon and Elena then leave in the car together and Elena says her goodbye to Jeremy.
In Home, Damon and Elena find out about Stefan's death from Caroline. Damon knows that Bonnie has a plan to bring her and Enzo back and thus he is confident that they will bring Stefan back as well. When Bonnie reveals that the Traveler who knew the spell to get people back from the other side is sucked into darkness, Damon breaks down. He starts throwing things around as the realization of losing Stefan forever hits him. He even threatens Bonnie to do something. Enzo interrupts them and reveals he has found another Traveler. Damon then meets Matt and Jeremy at Whitmore to plan their Travelers massacre. Killing them all will overwhelm the anchor and with the help of a spell they will be able to bring people back from the other side.
Later, Damon tells Elena that Matt and Jeremy are going to blow up the Grill and then he tells her that someone has to set off the explosion. Elena says no and asks if he sees a future with her. He says it’s all he has seen since the moment he met her. She asks why then would he go on a suicide mission and he says it’s only half of one because if he dies, he will be brought back with the others. He tells her it’s his choice and she has to respect it. He promises her that he will make it back to her. Elena looks at him for a moment and then kisses him passionately. When they pull apart Damon says it again "I promise."
While waiting for the signal from Liz, Damon sits outside of the Town's city line and drinks a bottle of alcohol. When he gets the confirmation from Liz that the plan is on go, he sits in the driver's seat of his car and proceeds to drive into town, but Elena gets in the passenger seat besides him. Elena says, "You said to respect your choice. Now you can respect mine." Damon looks somewhat shocked that Elena would be willing to die with him so that they're together rather than let Damon die alone. Seconds later the car plows through the Mystic Grill filled with the Travelers, Damon and Elena give each other one last longing look. Elena is about to tell Damon that she loves him but he tells her he knows. They both die ending up on the Other Side.
Elena and Damon find Bonnie. She tells them to pass through her, find their bodies on the Other Side and come back quickly. They both nod and pass through Bonnie. Damon wakes up on the Other Side but sees Liz on the ground. He tries to help her but struggles. Alaric finds him and together they rescue Liz. He then says "Friendly advice, when you get the girl, don't blow her up." Damon laughs and says "Good to see you too, buddy." Later they both go to Bonnie to pass through her and return to the land of living. Alaric goes through Bonnie and Damon pauses to find out where Elena is. Bonnie assures him that she has returned and then Damon tries to pass through her but nothing happens. They realize that Liv who was performing the spell to bring them back has stopped it making Damon unable to return.
It is time for Damon to say goodbye to Elena. He finds her crying hysterically in the crypt and she says "You lied to me". A ghost Damon says "Even if I wanted to apologize, you couldn't hear me, so I won't." He strokes her face and she appears to feel his touch but can't see his hand. Damon then says to Elena, "You are by far the greatest thing that has ever happened to me...The fact that I got to die knowing I was loved... is the epitome of a fulfilled life...It is never going to get better than this. I peaked." Elena distraught with grief makes one small plea to Damon, "Please, please come back to me." Damon then says goodbye and disappears.
Later, Damon finds Bonnie and the ground begins to shake underneath them. "This place is going down isn't it?" Damon says. She knows there are a thousand other people they'd both rather be with, but they take each other's hand as the light gets brighter and they wait for whatever is coming. "Think it'll hurt?" Bonnie asks. "I don't know-" Damon says, and then he's cut off by the bright white light. The fates of Damon and Bonnie are left unknown at the end of the episode.
In I'll Remember, its been four months since Damon and Bonnie died. Unable to accept Damon's death, Elena is seen eating special herbs that lets her hallucinate Damon. She describes her day to him and asks about his. Damon jokes about Alaric coming back to life to become a college professor. They both laugh and then embrace each other. Later, Elena hallucinates Damon in a car, he wonders if she's not visiting Bonnie because he knows Bonnie would agree with Luke that she needs to move on. Elena asks him to not talk about this.
Taking these herbs is making Elena very thirsty and so she decides to feed from a girl who she encounters on the road. Elena gets out to offer directions, but instead chomps down on her neck. Damon tells Elena to go easy, saying she nearly killed the last one and the one before that, and the one before that. Elena says she's still hungry and continues. She is later stopped by Caroline who confronts her about what she has been up to. After her talk with Caroline, Elena returns to her car and is comforted by Damon.
Later at the crypt, Elena chugs another potion of her herbs and when Damon shows up she tells him he's not even real, just her subconscious tricking her. She says seeing him is making her hurt people. He tells her to move on if she needs to. Elena thanks him for saving Stefan and Alaric and giving her a love full of passion and adventure. She tells him good-bye. She kisses him and expects him to be gone, but he's still there as Elena can't let him go. Then he starts asking her how long until she goes running back to Luke, telling her she's going to feel a lifetime of agony and grief. She trashes the crypt and collapses crying. But Damon is still there. At the end of the episode, we finally see Damon and Bonnie. He makes Bonnie breakfast and the two smile at each other, leaving it unknown where they are.
In Yellow Ledbetter, it is finally revealed what happened to Damon and Bonnie. The episode starts with the continuation of the ending scene of Season Five finale, Home. After the bright flash of light on the Other Side. Damon and Bonnie open their eyes to find nothing has changed. They're still standing in the forest, but now it seems like they're alone. They walk into Mystic Falls and Damon can tell he's still a vampire. The Mystic Grill is still standing despite the fact Damon blew it up an hour ago. There are no people anywhere.
After a while, Damon and Bonnie still haven't found anyone but notice all the cars seem at least 20 years old, but new. They come upon Elena's not burnt to a crisp house and Damon picks up a newspaper. It's May 10, 1994. Bonnie recognizes it as a week before something. Suddenly, there's a solar eclipse. Bonnie reminds Damon about her Grams telling Bonnie that she made a sacrifice so Bonnie could find peace. She figures Damon tagged long when they held hands as the Other Side disappeared and if magic got them there, it should be able to get them out. Bonnie tests her magic, but it's still gone.
Later, Bonnie comes home to the Salvatore house to find Damon making pancakes, chugging booze and dancing to Salt N' Pepa's "What a Man." She got a grimoire from her Grams' empty house and hopes she can reteach herself magic. The paper says May 10, 1994 again. They're both surprised when suddenly there's another solar eclipse. Sometime later, a sad Damon is seen reminiscing about a memory of Elena. During dinner, Bonnie tells him she misses everyone too. Damon notices Bonnie finally got the crossword clue that was stumping her (Yellow ledbetter). But she didn't. It's filled in, but neither of them did it. They both realize there are not alone after all.
In Welcome to Paradise, Damon and Bonnie go for shopping in a grocery store. He is not willing to admit that someone else must have filled in Bonnie's crossword puzzle. Then she notices pork rinds aren't on the shelf where they have been for the last four months. He doesn't argue. They hear music playing and Bonnie goes outside to see a kid's carousel turning. Damon tries to look for a mechanical reason for the carousel starting. Bonnie reasons that if there's someone else there, it's not Damon's hell, which means her Grams put them there and there's a way out.
Damon is ranting about Bonnie being useless without her magic when he notices his car in the parking lot. Overjoyed on seeing his car, he goes and sit inside it. He then remembers his last moment with Elena when she was about to say I love you. He then tells Bonnie that when he returns to Elena, the first thing he will say to her is how much he loves her. Damon is forced to admit someone must have put his car there. Then they both see something between the cars.
Damon and Bonnie inspect the cars in the grocery lot and realize what they saw was a tarp on a truck blowing in the breeze. Then the carousel starts itself, on a timer. Damon thinks he left his car in the lot in 1984 and Bonnie finished the crossword puzzle. He thinks it means they're never getting out. Bonnie gets angry about his lack of hope and tells him to just end it if he's serious. Damon heads to the empty, full-stocked liquor store. He sees someone eating chips in a lounge chair. He introduces himself as Kai and offers Damon a pork rind.
Damon quickly loses patience with Kai, who he realizes has been following them. Kai urges Damon to have a drink before he explains. Damon takes a long pull of his favorite bourbon off the shelf as Kai confesses the reason he's been following them is because he wants to kill Damon. As Damon has a sip of his bourbon, he spits out vervain realizing Kai spiked his drink. With Damon lying wounded on the floor, Kai breaks an umbrella in two and jams it through Damon's hand. Damon manages to get up and comes after him, but Kai cracks all the bourbon bottles with the umbrella, shattering their vervain-laced contents all over Damon. Then Bonnie shows up. He taunts her as the "useless" one. Bonnie surprises him when she is able to lit a candle with her magic. She asks Damon to run, then she surrounds Kai with flame as Damon comes up behind him and knocks him out. Kai wakes up tied to a chair by Damon's fireplace. Kai tries to convince them that he is on their team. He knew Bonnie would save Damon and get her magic back. He says her having magic is the key to them getting out of there.
In Black Hole Sun, Kai wants to know what Damon did on May 10, 1994 but Damon doesn't want to talk about the worst thing he ever did. But he finally starts telling his story. In 1994, a no humanity Damon shows up on Stefan's doorstep, wanting to make amends. Zack Salvatore, the owner of the house, allows Damon in on Stefan's promise that he'll keep him in line. He further tells about Zach and Gail, the girl who was pregnant with his child. Kai guesses that Damon killed the pregnant woman. Damon then threatens him to reveal answers. Kai explains that they will return home by harnessing the power of the eclipse using a mystical relic called an ascendant and he just made a replica of it. He tells Bonnie his family had it last in the Pacific Northwest and asks Bonnie to perform a locator spell.
Later, Bonnie's locator spell works and homes in on Mystic Falls, and something very close to her. She puts her hand on Kai's pocket and he reveals he had the ascendant. He says it was another test of Bonnie's magic. Kai announces that Bonnie is ready and it's time for them to go home which makes Damon very happy. Kai stares at the sun through the ascendant. Bonnie notices a newspaper headline that reads "Family Massacred in Portland." The whole family was killed and the 22-year-old son Malachai is missing. Kai points out that not everyone died, he had a soft spot for one of his sisters. He cheerily tells Bonnie and Damon how he slaughtered his siblings members of his coven, although he has no powers. He says the Gemini coven banished him here. Bonnie deduces that this place is actually a prison created for Kai to which he replies "Yep. This isn't your hell, Damon. It's mine."
Bonnie announces to Damon that they can't let Kai out. She asks Damon if Kai killing a bunch of kids isn't a big deal to someone who's murdered a pregnant woman. Damon then finally reveals he in fact did killed the pregnant women. He says it was a relief when he killed Zack as he reminded Damon of his terrible deeds. At night, Damon is shown seeing a pic of him and Stefan showing that he misses his brother too.
Later, Damon finds Bonnie eating pancakes. She reminds Damon that Gail liked pancakes and Damon has made them every day. She thinks he's punishing himself, which means he feels remorse and this is what makes him better than Kai. Damon suggests they take the ascendant from Kai, but Kai sneaks up and explains why that won't work. He doesn't have magic of his own, but he can take it from others temporarily. He grabs Bonnie, then uses her magic to paralyze Damon as he lays out his ultimatum that he can either kill them both and use Bonnie's magic to go home, or they all can go home together.
In The World Has Turned and Left Me Here, Damon is extremely excited to return home and is already planning a date with Elena. However, Bonnie is skeptical as she still doesn't trust Kai. Kai then greets them and asks Damon to dig into the tunnels below because that's where they will wait for the eclipse as Bonnie performs the spell. Kai still doesn't tell Bonnie the spell and leaves to get some important things for the spell.
Damon finishes his hole and Kai comes back with his things. Bonnie insists that he show her the spell, but he refuses. So she dares him to take her magic. He grabs onto her, but she assures Damon it's ok and he won't kill her. Kai leaves her and Bonnie is now sure that Kai doesn't know the spell which means they no longer need him. Then she uses her magic and kills Kai. Bonnie pours over a spellbook as Damon drowns his sorrows over a drink as he thinks she ruined their chance of getting home by killing Kai. Bonnie suggests the Gemini Coven used a Bennett spell to make Kai's prison and that's why her Grams sent them there. She recites a few lines of a spell and Kai's ascendant opens. She realizes Kai couldn't kill her because he needed a Bennett witch to open the ascendant. With the eclipse about to start, Damon and Bonnie get ready to start the spell.
They go inside the tunnel and Bonnie puts a few drops of her blood on the ascendant and begins reciting. The ascendant responds and Damon takes her hand. She's about to start the spell when suddenly an arrow hits her in the side. Damon turns around and sees a very live Kai standing there with a crossbow. He tells them he's tried to kill himself many times but this dimension doesn't let him. Damon rushes to Bonnie and starts to feed her his blood, but then has to rush to Kai when he goes for the ascendant. Kai stabs Damon in the ribs with an arrow and Bonnie tries to inch toward the ascendant on the ground.
Kai and Damon continue struggling, with Kai twisting the arrow in Damon. Bonnie makes it to the ascendant. She tells Damon she's not going to make it, but he will. She uses her magic to flip Kai off Damon and drag Damon into the shaft of light caused by the eclipse. Then as Damon is yelling at her to stop, she tosses him the ascendant. It opens and the spell works, lifting Damon up into the real world.
Damon first visit Stefan who he is in their family crypt talking about how depressed he is post Damon's death. He confesses he's not doing well without Damon and can't seem to start over because he's lost. He throws his bottle and to his surprise Damon catches it. Damon says "What, I'm gone a couple months, you think it's ok to waste a perfectly good bottle of bourbon." Damon assures him he's back. Stefan can't believe his eyes and touches Damon to make sure he is real. Both of them hug tightly while crying with joy.
In The More You Ignore Me, The Closer I Get starts with where the previous one ended. Damon and Stefan are hugging each other and Damon tells Stefan he missed him too. He then tells him about being stuck in 1994 with Bonnie and that she sacrificed herself so that he could return. But the version they tell others is different that Bonnie was never there with him so that they don't feel the pain of losing her all over again. He then says he has to go meet Elena. But Stefan stops him and tells him about her compulsion to forget her love for Damon. Damon is shocked to hear this but ensures Stefan that the moment their eyes will meet, everything will be okay again.
Damon goes to see Elena, but she won't let him in her dorm room. He tries to reminder her how she felt about him and that the compulsion is a lie. Elena is about to open the door when Damon says "I hear you breathing. You have no idea how long I wanted to hear you breathe." This makes her scared again and she stops. Damon tries a little more but at last says he is gonna kick the door open. Elena then finally opens the door, but jumps out of the window before he can see her. Damon then visits Alaric in his office who is happy to see him and asks him how he has been. Damon sarcastically says that he is great. He is not happy with Alaric's compulsion of Elena, but Alaric explains that Elena was a mess without him. He'll lift the compulsion when Elena is ready. Damon is not pleased, but leaves peacefully.
Later, in Elena's dorm room, Damon notes that there are no pictures of him anywhere. So he picks Elena's graduation picture and draws a cartoon picture of himself around her. Jeremy enters and wants to know why Bonnie didn't come back. Damon says Bonnie wasn't with him and found peace in a better place. Damon calls Bonnie's phone to thank her and apologize when he gets a call from Elena who says she can't avoid him forever so she is ready to meet. She asks him to come by her dorm room and Damon says he will be there in a bit lying about the fact that he was already there waiting for her. Damon then checks his appearance in the mirror and hears someone walk in. He think its Elena but its actually Tripp who manages to capture him.
Damon wakes up chained in the back of Tripp's van with Enzo, who tells him Stefan probably didn't tell him about the hunter in town because Stefan's the one who put him there. As they are approaching the Mystic Falls border, Alaric shows up and asks Tripp for a lift. Tripp ends up driving them all across the border. Stefan manages to save both Damon and Enzo in time but not Alaric. Though Jo, the Whitmore doctor saves Alaric, it is only after he has turned human which means he can no longer give Elena her memories back.
Later, over drinks, Damon is whining about how Elena is happy while he is miserable to Stefan. Stefan gives him the kick he needs to go see Elena and see what happens. Damon goes to see her and knocks at her door. They both take a deep breath and Elena finally opens the door. The episode ends with a cliffhanger of Damon and Elena coming face to face for the first time since his return. Damon has a look of awe on his face while Elena looks at him nervously.
Going into the next episode, Do You Remember the First Time?, Damon and Elena finally face each other for the first time since he returned. Damon is hopeful that Elena might be remembering something but she confesses that all she remembers is the pain he has caused all the people she loves. She apologies and says she just doesn't feel anything anymore. A heartbroken Damon leaves. Later, he visits Alaric in the hospital and says that he is glad that he is alive but still taunts him saying that if he would have actually died then the compulsion would have weared off and Elena would have remembered loving him. Jo then arrives and releases Alaric so he can come as her date to the hospital fundraiser.
At the fundraiser, Damon meets Alaric and Jo and she is surprised to see him. Alaric teases him and says he is here to stalk Elena. Elena enters then but she is not alone, Jo tells Damon about Liam who is Elena's date at the fundraiser. He introduces himself to Liam, prompting Elena to have to explain why Damon isn't actually dead. Damon says it was more of an emotional death. He compels Liam away to dance with Elena. During the dance, Damon tells Elena about the first time they danced at the Miss Mystic Falls pageant and how they both got lost in that moment. She tries to explain again that she doesn't remember them and leaves to get some air. However after some time, Elena finds Damon and tells him she wants to try to remember them. She asks him to take him to the last place she told him she loved him.
Damon takes her to the Mystic Falls border, the last place she told him she loved him. But Elena doesn't remember joining him in the car to crash into the Grill. He tells her about their most memorable moments, a motel ice machine, the night of her graduation when she told him she was in love with him, and his favorite, the summer night before she went off to college when she took him to watch a meteor shower and it started raining. Elena stops him and says that this is not working and confesses that all she sees in him is a stranger. Elena then takes a deep breath and crosses the Mystic Falls border while Damon tries to stop her. Memories come flooding back but unfortunately she starts drowning. Damon yanks her back across just in time and tells her that he wont risk her life for her to remember their love.
Damon walks Elena back to her room and she tells him she remembered a tiny bit of the meteor showers and the rain. She asks him what happened after that, but he tells her that she's better off without him and he lets her go. She again asks him what happens after it starts raining but he lies and says they both got wet and muddy and hence drove home. Out in the woods, Damon remembers what actually happened the night it rained under the stars. She wanted to wait for it to stop raining but they ended up kissing each other. In between their kisses, she asks him to promise her that this is forever and he does that. Back in the present, Damon carries his bottle of bourbon through the cemetery, drowning his sorrows. Then he sees Bonnie's teddy bear leaning against a crypt and knows it means she is still alive.
In Fade Into You, Damon, Stefan and Alaric make a trip to Portland to talk with Gemini coven so that they can help them bring back Bonnie. On their way, Damon and Alaric tease Stefan about Caroline. They keep telling him about her wonderful qualities and so Stefan should date her. They reach the supposed location of the Gemini coven that Stefan visited four months ago but its just an empty field. Damon taunts Stefan with Bonnie's bear about how he broke Caroline's heart. An annoyed Stefan grabs it and drop-kicks it into the field. As the bear crosses an invisible plane, the bear's Bonnie magic kicks in, revealing a house.
At the Gemini house, Alaric remembers what Jo said about putting her magic somewhere and they deduce Bonnie put hers in the bear to keep Kai from using it to get out. Stefan and Damon can't enter the house as they haven't been invited in so Alaric gets inside and looks around. Alaric has found pictures of Jo and news articles about the attack. Damon notices a picture of Jo and Kai together and realizes they're siblings. A man joins them out in front of the house and introduces himself as Joshua Parker, Kai's father. Damon shakes his hand and Joshua uses magic to make everything invisible again. As a result, Alaric and Stefan can't see them while Joshua paralyzes Damon and takes him inside.
Damon wakes up inside the Gemini house and Joshua explains he just wants answers. Damon is happy to provide them in exchange for the ascendant, but Joshua isn't inclined to give him the key to his sociopathic son's prison. He explains to Damon that if Kai gets out, he'll go straight to Jo and kill her for her power. Damon suggests he could just kill Kai, but Joshua says if Kai manages to kill Jo he becomes everyone's problem. Joshua starts a spell to kill Jo as she has the ascendant. Damon tries to stop him from hurting Jo but he paralyzes Damon again. Stefan manages to enter the house after Jo invites him in over the phone. He tries to stop Joshua but he uses magic and becomes invisible again.
Damon, Stefan and Alaric prepare to leave Portland, but Alaric refuses to get the ascendant from Jo and risk her life by possibly freeing Kai. So Damon compels him to do it. Later, Damon is drinking at the bar and Elena joins him. She tells him that he should have told her about Bonnie and then taken her to their search trip. He continues to taunt her about the compulsion thing. Elena then asks him about what did he and Bonnie did for months. He says bicker mostly. He tells how he still can't really believe she sacrificed herself so he could come back, but knows it was because of how much he talked about Elena. Elena tells him about her break up with Liam and then says there is this feeling inside her that she can't seem to shake. But she is at a crossroads if she should live a normal life or risk everything for this feeling. Damon asks what is its gonna be and she asks Damon to help her bring Bonnie back so Bonnie can help her decide what to do with her feelings. She holds his hands and Damon smiles and says sure.
In I Alone, Damon and Stefan are waiting for Alaric to show up with the ascendant after stealing it from Jo. Stefan warns Damon that Alaric is going to hate him for compelling him. But Damon instead taunts him about his and Caroline's ruined friendship. He says it might seem easy being the bad guy but soon you will feel lost and talk to strangers on the road. Alaric then shows up with the ascendant and Damon compels Alaric again, to forget any of it any happened. After getting the ascendant, Damon and Elena meet Liv in the woods. She gives them vials of her blood to drink to link them to her so she can find them and bring them back, plus an extra for Bonnie. She tells them they have about eight hours to find Bonnie and bring her back. They her blood and then Liv pours the Bennett blood on the ascendant and recites the spell. They both land up in the Prison world.
Elena and Damon first go to Salvatore House and search for her but she isn't there which makes Elena wonder if Kai has done something to her. Damon tells her to not be negative but Elena finds Bonnie's blood on the cushion. Damon then uses a pager to contact Kai. While waiting for Kai's call, Elena wonders around the house and comes across Damon's video journals which he made during his time in the prison world. She starts playing it but Damon stops her from seeing it. He tries to cover it up by saying its an audition tape but Elena doesn't believe him. She tries to ask the truth but then the phone rings. Its Bonnie and she reveals to them how Kai left her to die in Portland and stole her blood. She tells them that she can make it to Mystic Falls in seven hours. As she hangs up, Damon starts to worry that Kai might be already out.
Later, Damon and Elena make blueberry pancakes together in the Salvatore kitchen. They sit down to eat them but before Damon can eat his, Elena makes fangs with the cream just like he used to do. Damon smiles and they start eating. Elena sees the news story about Kai's murderous rampage and wonders why Jo would hand over the ascendant. Damon tries to change the topic but is finally forced to admit that he compelled Alaric to steal it from her. Elena storms out of the kitchen and Damon goes after her. She thinks that his dedication to bring Bonnie back is only for her to see what a great guy he is and so she falls for him all over again. Elena lashes out at Damon for being so selfish and leaves.
Damon goes to see Elena on the Gilbert porch. He tells her that on May 10, 1994 he was mad at Stefan and acted out and a lot of people died. He has felt guilty ever since, which is why he thought that this was his personal hell. But Bonnie wouldn't let him believe it and had hope for both of them. He confesses that they finally managed to become friends and that he is doing this for Bonnie and not for her. Elena smiles at this and Damon goes and sits beside her at the swing. When Elena says that the swing used to squeak, Damon says it did but he fixed it. He confesses that he used to come here everyday because this was the closest he had of a picture of her. Elena starts to get nostalgic about her old house and Damon encourages her to go inside. Before opening the gate, she apologizes to Damon for compelling away the memories saying it was of both of them. He smiles and say they will make new ones and touches her face gently. They both smile and are having a moment when they feel something changing around them. They find themselves back in the cemetery in real world. Tyler and Liv are there and they both look sorry as Tyler says Kai is after Liv and they have to go to Mystic Falls.
Elena and Damon are sitting beside the grave site, sad that their plan failed. But Damon gives her hope saying that as long as they have the ascendant they can try anytime. But then Kai finds them and uses magic to break the ascendant. Damon is eager to kill him, but Kai still has Liv's magic and incapacitates him. He goes towards Elena who is trying to fix the ascendant but he starts a spell to burn both of them. He uses invisibility to protect himself from Damon but he menages to locate him and sends Kai across the border to Mystic Falls. The fire stops but the ascendant is destroyed. Damon comforts Elena and asks if she is okay as Kai tells them he is ready to create havoc in Mystic Falls without any vampire to stop him.
Later, Alaric confronts Damon in the woods. He doesn't want to hear Damon's excuses that Kai getting out isn't their fault and punches him. Elena arrives and tries to comfort a sad Damon. He tells her he left Bonnie a note to meet them at the porch and knows she has probably reached there right now. He confesses how she sacrificed so much for all of them and they were supposed to be there for her but now is left all alone in the prison world.
In Christmas Through Your Eyes, Elena and Damon are still looking for a way to bring back Bonnie. They are looking in Alaric's books for something that resembles an ascendant. When Damon catches her staring at him, he asks her if she is watching him sleep. She teases him that she is watching him drool all over Alaric's textbook. Damon continues to search while Elena keeps staring him. When Damon notices it, she thanks him for helping Bonnie. Alaric then calls them to inform that Jo has gone missing. They all gather at Jo's apartment and Elena reports about the stabbing victims brought into the hospital last night and now one of them is missing. She also says that no one has seen Jo. Damon says they should find Kai and kill him. He thinks that since he hid the knife in a painting at Jo's apartment, Kai will come looking for it and he will kill him. But when he sees the back of the painting the knife is not there.
Later, Damon is searching for the twins at Whitmore and finds Luke. Rather than threatening him, Damon points out how dangerous Kai is and if he merges with Jo then how powerful he will become. Luke seems convinced and spills Kai and Jo's location. Damon and Alaric go to find Kai and Damon tries to apologize to Alaric for compelling him but Alaric doesn't forgive him. When they reach the tomb where Kai is holding Jo captive, they try to lure him out. Damon rushes towards him but Kai pushes him over the magic border. Damon starts to burn and steps back across, then Ric sneaks up on Kai on the other side and holds a gun to his head. He is ready to fire, but Jo comes out and tells him not to, because Luke and Liv will have to do the merge if Kai dies. Jo says she can beat Kai with some time to get stronger. Damon tries to convince Alaric otherwise but Alaric listens to Jo and spares Kai's life.
Sometime later, Kai is chained up across the border but Damon still tries to hurt him by throwing rocks. Alaric finds Damon and tries to reason with him. Damon is angry they won't let him kill Kai and Alaric points out how selfish Damon is being. Damon is talking to Elena through phone but the reception is horrible as unknown to him, Kai is sucking ll the travelers magic which was used in the anti magic spell in Mystic Falls. As he takes away all the magic, Mystic Falls is no longer magic free which means they all can go home again.
Damon tells this to Elena over phone who says that she doesn't know what they were or are supposed to be but after a horrible day she wants to see him and has something to tell him. Damon asks her to come over, he will cook her dinner and they can talk about their crappy days. While he is preparing for their dinner, he hears a familiar noise of his car and finds it hard to believe. He goes out and sees Stefan has repaired his car. He is rejoiced and hugs Stefan. When Elena reaches the Salvatore house, she sees a Mistletoe hanging on the door and laughs at Damon's clever antics. She knocks and Damon opens the door but he sees no one there. He closes the door and Elena is shocked when Kai appears behind her saying that he put a cloaking spell on them and then knocks her out.
In Woke Up With a Monster, Damon wakes up in Liz's room, who has been hospitalized after learning of her disease. He tells Liz that Elena texted him that something came up so she had to cancel their dinner date and that he is letting Jo practice magic in his house as he feels guilty for compelling Alaric. Caroline enters the room to check up on Liz. She tries to convince Liz to drink vampire blood and asks for Damon's support. However, Damon tells Caroline that he has never heard that vampire blood can cure cancer. He then leaves to check on Alaric and Jo.
When Damon reaches the Salvatore Boarding House, he gets a call from Elena. She quickly says that Kai has her at Mystic Falls High School and cuts the call. Damon then reaches Mystic Falls High School with Liv and waits for her to perform a cloaking spell on him so that he can free Elena from Kai. But Luke appears and makes Liz disappears as they have something important to do. Damon then calls Alaric for a back up. Jo agrees to help them as cloaking is something which she has performed as a child as well. Jo arrives at the school and cloaks Damon and herself. When they are sure that Kai can't see them, they go to find Elena.
Damon finds Elena in one of the class rooms and frees her. Jo is able to make Elena invisible as well but she isn't strong enough to hold the spell for long. While in the hallway, Jo is ready to fall over and Kai finds the trio after her cloaking spell wears off. Damon tells her to run as he faces Kai, not prepared for how powerful he is. Kai cloaks Elena then stops Damon in his tracks. Damon is able to throw a broom handle into Kai, but it's only an illusion of him and it is actually Elena. Kai brings Damon to his knees then he takes off after Jo. However, Alaric and Jeremy arrive in time and manage to knock down Kai.
Later, Damon removes the spear from Elena, but she is still weak and gasping. She thinks there is a splinter still insider her. As Damon tries to find it, she gasps for breath and tells him if there is anything he wants to say, now is the time. Damon starts panicking but then she starts laughing, revealing that she was tricking him. They both hold hands as they smile at each other. Alaric and Jo arrive and he asks Elena if she is okay. Elena looks at Damon and says, "I have never felt more alive".
Later, they all are at Alaric's apartment, making arrangements to keep Kai unconscious. Elena asks Damon on a dinner but Damon tries to tease her saying that every time they try to go on a date, something bad happens like him being sent to a prison world or Elena's feelings getting compelled. Elena tells him to stop sulking and let her take him to dinner tomorrow. Damon replies that they are going to find out about it tomorrow and both share a flirtatious smile. Jo then offers to clean Elena's wounds and Elena leaves with her. Alaric arrives and tries to convince Damon that Jo will be manage to defeat Kai and win the merge. Damon still remains skeptical but toasts with Alaric to their women making crazy decisions and them loving them more.
In Prayer For the Dying, Damon is with Elena in Alaric's room and notices she has a new daylight ring due to Kai melting the other one. Elena tells him it's his job to keep a watch over Kai and not smother him with a pillow. They joke a little bit before she walks out the door and is called to down to find out that Caroline fed Colin vampire blood and and it sped up the cancer and killed him instead. Jo and Damon then talk and since it's a magical problem with Liz, he hints that he has solution. He and Elena then talk and says that everyone cares about Liz and they'll fix what's going to eventually happen to her. Colin confronts Caroline and tells her he wants to die, and then Damon extracts Colin's heart out. He tells her that the blood transfusion didn't work and she didn't just kill him, but also her mother. He catches Tyler pulling out the wires and oximeter from Kai, but Damon grabs his throat and hears what Tyler has to say and thinks Kai can siphon the magic out of Liz. Damon calls Liv using Tyler's phone and tells her that he wants to talk to Joshua. He asks him if the Mercury-Venus conjunction could help with the Merge and tells him to get the twins to merge since Kai is going to be on the loose and hell-bent on merging with Jo instead. Kai wakes up and tries to use magic on Damon but can't since it all drained away. Damon tells Kai that he can get more magic for him and where to get it, but Kai has a fee he wants. He tells Kai to siphon the magic out of Liz and Jo walks in asking what he's doing there. They talk and he tells her that Kai wants to merge that night and she says she can't since she's not ready. Before Damon can say anything else, Kai breaks his neck. After waking up, Damon walks in and sees Elena trying to compress Liz when she doesn't respond and she tells him to find a doctor. He comes in with one and the doctor shocks Liz. Unfortunately the doctor cannot get Liz to wake up. A few minutes later she does wake up and he and Elena then kiss after she wants to get out of the room for a few minutes. Damon arrives at the park where Luke and Kai merged, and notices Jo cradling Luke's head in her arms. He offers to give Luke some blood, but she says it wouldn't work and Luke takes a breath and opens his eyes, but unfortunately dies. Kai is standing near them grinning and Damon moves towards him, but Kai disappears.
In The Day I Tried To Live, in the kitchen, Elena lets Damon know she's OK with them having kissed by kissing him again. They're interrupted by Kai. He needs their help finding Jo. He explains that after the merge, in which he killed Luke and took his powers, he seems to have absorbed some of Luke's humanity. And he feels bad, which is really harshing his sociopath buzz. He tried writing a letter to Jo and found himself crying over Jo. "I really feel strongly that Jo needs to know how sorry I am for destroying our family," Kai says. Elena thinks of something he can do for them in return. Kai says he can't repair the ascendant. Damon plays on Kai's newfound emotions about it being Bonnie's birthday and convinces him to send a message about where to find magic. Damon suggests they tell Bonnie to go to Nova Scotia and find Qetsiyah's magic-soaked blood on Silas's tombstone. Kai prepares Elena, Damon and Jeremy to pay a ghostly visit to Bonnie. He recites a spell and suddenly they're in 1994 Purgatory. But she can't hear them and they can't touch anything. They see Bonnie watching footage of her with Damon and then cracking the oldest bourbon in the house. Damon tells them about a pact they made if they couldn't take Purgatory anymore: drain the bourbon then kill themselves. Suddenly they're all back in the real world. Kai's nose is bleeding from the magic drain. Damon scribbled notes about Nova Scotia in a book, they just need to get her to see it. Jeremy volunteers to go alone, even though it could mean he gets stuck there. Damon heads for the same bottle of bourbon Bonnie is drinking, determined to drink it with her. Elena wonders if she'd be with Damon if she were still human. He says she wouldn't. Elena doesn't love the answer and tries to leave the room, but she's blocked by a spell. Liv goes looking for Kai. Damon hears Liv below them and kicks a hole in the fire place, then drops the special bottle of bourbon down. The booze hits the flame below and knocks Liv off her feet and frees them. Damon feeds Kai his blood to heal him, Elena is able to wake up Bonnie. Later, Elena tries to give Jeremy permission to move on. She encourages him to go to art school like he wants. Elena finds Damon and gives him a speech about being ready to move on from her human past, and acknowledge that no matter what happens, she keeps finding her way back to him. He kisses her and they fall into bed.
In Stay, Elena and Damon sit down with Jeremy's principal to try to convince him to let him graduate early to go to art school. The principal isn't buying it, so they try it Damon's way. They already compelled him into art school, so they compel the principal to let him go. At the Grill, Damon and Elena bring Jeremy the good news that he "graduated," although Elena 'fesses up to the compulsion. Damon even got him a going away joint. Damon finds Liz in her office with her open case files. Damon helps her close a few by confessing to most of them. She worries that Damon is behind Elena's parents' death, too, but he promises he's not. She plays him an urgent message Miranda Gilbert for her two hours before her death. Liz asks Damon why he and Stefan were in town the night of the crash. He came to lay flowers on his mother's grave. Liz doesn't entirely believe him, but he changes the subject to why the Gilberts were on Wickery bridge when it was out of the way, pointing out there were no skid marks and the trunk was full of luggage. They were going somewhere. Liz calls Elena and Jeremy, but Elena is too stoned to answer. When Damon calls, he tells her to sober up and get to Liz's. Damon sees Liz get light on her feet. Later, Elena relays the news to Damon, who tells Liz. Jeremy remembers his mom caught him smoking pot in his room that night and put on a big show of getting mad and calling the sheriff. The luggage was from a planned surprise trip to the lake house that was ruined by a storm. Liz remembers the storm also put a power line across the shorter route home, which is why they were on Wickery. The bridge had a drainage issue before it was renovated and was probably slick, thus no skid marks. Liz sadly realizes there's no mystery. She asks Damon to call Caroline and tell her she can surprise her tomorrow. Liz leaves her badge on her desk and walks out. At the Salvatore house, Elena gets the update from Damon but urges Jeremy to go on with his plans to leave town. Alaric offers to take him to the airport. Damon gets Liz settled into her own bed. He can tell she's disappointed there's no bigger reason for the Gilberts' death. Liz allows herself a few moments of self pity and gets upset that she's lived a life as a good person and is still dying. Liz tells Damon to tell Caroline how proud she is of her, but he says she can tell her herself. Damon tucks her in and takes her hand. Damon shares that he wrote his mother's eulogy but then didn't go to the funeral. Liz asks him to write her -- just nothing dirty. Liz asks for a drink. Damon turns around to get it but when he turns back, Liz is unconscious. He takes her to the hospital and she slips into a coma. Stefan shows Caroline how to share dreams and Liz slips away while everyone is at her bedside.
In Let Her Go, in the kitchen, Damon is trying and failing to write Liz's eulogy. He thinks it's Liz's way of making him deal with not being there when his mom died. Caroline is just trying to get through the next few days, but Damon tells her those aren't the bad ones, when she's surrounded by friends trying to make her feel better, it's what comes after.In the morning, Caroline makes a to-do list following her mother's death. She wants her mom celebrated and buried by the end of the day. Damon remembers back to after his mother died. Stefan can tell that Damon is struggling with the eulogy. But Stefan has other things on his mind. "I need your advice, and I need you to not be a dick about it because I have no one else to ask," Stefan says. Stefan tells Damon about kissing Caroline. Damon asks Stefan if he's in love, then seeing that Stefan isn't, advises him to bail now before Caroline gets hurt -- just not today. Damon is still laboring over the eulogy. Elena worries that Caroline isn't handling things well. Elena suggests the eulogy isn't about Damon, or even Liz, but about Caroline and what she needs to hear. Damon remembers the past, arriving after his mother's funeral. Young Stefan is in tears and upset that Damon didn't just stay good-bye. Liz receives a full policeman's funeral. Then it's Damon's turn. "Liz Forbes was my friend. In her last moments she asked me to pass along a message to her daughter....Your mom wanted you to know how proud of you she was, and she should be. You're a beautiful, strong woman and a generous friend. A bright light in a sea of darkness. She said you were extraordinary and you are, and so was she," Damon says, adding that Liz was a hero to everyone including him. Stefan keeps looking at Caroline as Damon talks. Caroline gets up and sings "Go in Peace" for her mother. At the Grill, Stefan compliments Damon on his eulogy. He remembers failing Stefan by not doing their mother's eulogy and he didn't want to fail anyone. Stefan tells Damon he thinks he was wrong, he definitely feels something for Caroline. Damon tells him to stop wasting his time with him. "I think she could use a piece of news like that today," Damon says. Damon comes home, leaving a voice mail for Elena and finds pancake fixings in his kitchen -- and Bonnie, surprising him, leaps into his arms. Bonnie tells him she was in his house in 1903 in the prison world. She still had her camcorder on and plays it for him. Damon sees the woman Bonnie saw. It's his mother.
In The Downward Spiral, him and Kai are at The Salvatore Crypt. Damon is breaking open his mothers coffin. Kai talks about Bonnie and how happy he is shes no longer stuck in the 1994 prison world. Damon is annoyed with Kai and continues to break open Lilys coffin. Damon tells Kai that his mother died and that wasn't her in the recording in Bonnie's camcorder in the 1903 prison world . Kai tells Damon its possible if shes a vampire. Damon finally breaks open the coffin to see no one is in there. He realizes now its possible his mother is a vampire. Later at the at the Salvatore boarding house. Damon receives a phone call from Stefan. They talk about Caroline, her humanity being off and her feelings for Stefan. Stefan asks Damon to look in the area for any missing people. Kai is there listening to their conversation he asks Damon why he didn't tell Stefan about Lily. Damon tells him its not the right time. Damon asks Kai for the ascendant so he can send him to the 1903 prison world to confirm if his mother is alive or not. Kai agrees only if Damon take him to go see Bonnie. A while later Bonnie and Damon talk over the phone to talk about Caroline, Elena and Kai. Damon tells her to have fun at the rave. Kai heard the phone call and still wants to see Bonnie. Kai tells Damon about Lily he tells Damon that Lily was in New York on her way back to Mystic Falls. Damon and Kai arrive at the the rave where Kai sees Bonnie. Damon arrives at Bonnie's dorm. Shes angry at Damon so she tortures to make him feel what she felt what Kai did to her he leaves. Damon goes back to the boarding house. Damon has a talk with Kai and he wants to know why Lily is stuck in the 1903 prison world. Kai tells him shes there for a reason. Damon is very angry so he grabs Kai's throat and forces him to talk. Damon wants to get Lily back. Kai tells Damon that Lily is a ripper. Kai then tells Damon that she and the heretics were captured and sent to the 1903 prison world. Kai also mentions that Lily has killed thousands of people. Damon doesn't want to hear anymore he demands Kai to shut up.
In A Bird in a Gilded Cage, when Stefan arrives home, he quickly asks Damon where they keep all of the weapons. Damon confronts him about turning off his humanity. But Stefan breaks Damon's arm before he can inject him with vervane, then warns him to stay away and leaves. Elena comes home to find Damon working out his rage on the furniture, hitting a chair repeatedly with a bat. He tells her his mother is alive and a ripper. "It makes perfect sense, Stefan was always a mama's boy," Damon says. Elena gets an idea, but Damon thinks you don't fix one ripper problem by unleashing another. Damon goes to Bonnie for her help to work with Kai to get to 1903 which she reluctantly agrees after some convincing. At the Salvatore house, Bonnie, Kai, Damon and Elena prepare to go to the 1903 prison world. Once they transport, they are greeted by the world covered in snow, Bonnie and Kai break off to look for the 1903 ascendant, because it can't travel between worlds, and Elena and Damon go to look for Damon's mother. Damon and Elena finds his childhood home, Elena finds a picture of Stefan but thinks that it is Damon and makes a comment that he was so cute. Damon reply's with that's Stefan and hands her a photo of Damon. Once Damon is done swearing that his mother is dead to him, she arrives. Lily serves Damon and Elena tea and explains her life. She drained all the blood nearby and now survives on two drops a week. When laughs when Damon tells her that Stefan ripped their father's throat out. When Lily admits she hated her husband, Damon guilt's her for leaving him and Stefan with him. After Damon and Elena explain the need to turn Stefan's humanity back on, she agrees. Then she mentions her "traveling companions". She introduces them to a table full of mummified vampires. Lilly explains the mummified vampires saved her from herself and her ripper tendencies. She says they gave up their blood rations for her and she learned to control her blood lust. Damon thinks she's wackadoodle. When Lily goes to get the last of the blood to revive them, Elena notices the ascendant is on the table. Damon tells Elena that Bonnie isn't looking for the ascendant. As the aurora borealis begins, Bonnie joins Damon and Stefan. When Damon explains to Lilly that they're short one witch and her friends can't go, Lily refuses. She insists that the vampires are her family and she won't leave without him, but Damon threatens to leave her, too. As Bonnie recites the spell, Kai arrives and watches Damon, Elena, Lily and Bonnie disappear out of the prison world. Back at the Salvatore house, Lily admits to Damon that she did visit Stefan the night of her funeral. Stefan only remembers her as an angel. But when she leaned down to whisper in his ear, all she could hear was the pound of his blood, so she fled for their sake. She assures Damon she missed them twice as much as they missed her. When Lily asks again about getting her friends back, he assures her they'll be going back soon. Elena tries to convince Damon to give his mother some time. She points out it's never a waste of time to look for the best in someone. Damon and Elena start taking each other's clothes off making out very heavily. To then be interrupted by Bonnie who looks startled. When Elena leaves, Bonnie thanks Damon for helping her find closure. Damon turns on the water so his mom can't hear, then tells Bonnie the crazy woman upstairs wants to go back to 1903. But he agrees they're never going back. Bonnie gives him something from the 1994 prison world, the cure for vampirism that she got on her road trip to Nova Scotia. He's not sure if he wants it for Elena anymore. "It's up to you," Bonnie says.
In I Never Could Love Like That, inside the house, Elena and Damon have a cozy morning with his mother playing house downstairs. When Elena goes to get dressed, Elena nearly stumbles upon the cure but was luckily looking the other way when it was is sight. Damon looks at the cure, and then shuts the drawer. At breakfast, all Lily can talk about it returning to her prison world to get her friends. Lily casually brings up the fact of being human hinting that she heard Bonnie and Damon last night. Elena then gets a text from Jo that someone has been killing people at Whitmore, and apologizes for having to leave. Damon makes an angry gesture to his mother as Elena leaves. On the road to Whitmore, Damon tries to prepare his mom to talk to Stefan and bring his humanity back. She states that she overheard Damon and Bonnie talking about the cure. She knows he's afraid he'll lose Elena if he gives it to her. He tells his mother that she needs to give a performance of a lifetime because she claims that she wasn't coming back to America for Stefan and Damon like he thought. At Whitmore, Lily worries how she's supposed to connect with Stefan. Damon suggests she tell the story of how she came back to get them, but Damon realizes she wasn't coming to get them. Lily admits she's been struggling to reconnect with how it felt to be their mother. She explains her "new" family helped her find herself again, but she lost any feelings she had for her old family in the process. Damon calls Elena, who then suggests that Lily would just simply try lying to Stefan if they hope to get him back. Damon orders Lily to give it her best shot, but she was assurances that they'll go get her people. She points out he's lying to Elena by not telling her about the cure and he gives her the ascendant as assurance. Stefan and Caroline are interrupted at the bar when Damon and Lily walk in. Damon gives Tyler his keys to his car to take Matt for help. Caroline realizes Lily is there to turn Stefan's humanity on, and then he's supposed to turn on hers. So she stakes Stefan in the back and runs out of the bar. With Stefan, Lily tells her she's a ripper like him. She pours on the motherly warmth, telling Stefan the story he wants to hear about visiting him the day of her funeral. Damon watches as she reacts the sweet sentiments he fed her earlier. She promises never to leave him again. It works. He turns his humanity back on and hugs his mother with tears in his eyes. Stefan takes a few moments to contemplate all the killing he's responsible for then resolves to go find Caroline. Elena tells Damon she was jealous when she heard about Jo's pregnancy because she always wanted a family and knows it's never going to happen not that she's a vampire. Damon asks how she could feel if things could be different, but doesn't elaborate.
In Because, Stefan takes Caroline to a B & B for a break, telling her his mom was full of lies. It's part of his plan to convince Caroline his humanity is still off, then torture her until she breaks. He calls for towels, planning to eat whoever brings them. Going over the plan with Damon and Elena beforehand, Damon is delighted to tell Elena that Stefan and Caroline slept together. They plan to drain Caroline and make her weak, then overwhelm her emotions. Elena has a letter from Caroline's mom that arrived after Caroline flipped her switch. Damon arrives with the towels and shoots Caroline with vervain darts, then Stefan to stage the scene. When they wake up, Stefan tells Caroline they got caught. Their room has been vampire-proofed. Damon drops by Bonnie and breaks the news about leading his mom on about returning to the prison world. Bonnie isn't happy to learn Lily might be her problem soon. She also can't believe Damon hasn't told Elena about the cure yet. Elena is reeling from the fact Caroline burned the letter from her mom. Damon asks Elena where she'd be in five years if she was human. In a loft in Tribeca, with Damon owning a bar and Elena working in the surgical residency program. She wants two kids. From upstairs, Caroline gets annoyed eavesdropping and decides to distract herself by kissing Stefan. Damon interrupts with crime scene reports of all Caroline's kills, asking Caroline what her mom would think of it. Caroline turns on them and asks Damon what it feels like to not be able to give Elena the life she wants. With Damon, he prods Elena into admitting she will never be 100 percent OK with being a vampire, but she's OK with that if it means spending eternity with Damon. They're interrupted when Lily calls to demand Damon return the ascendant. She found the cure and threatens to destroy it if he doesn't. Damon finds Bonnie in the dorm at Whitmore about to destroy the ascendant. He tells her his mom has the cure, but Bonnie doesn't want to risk her life by letting the heretics out. Bonnie says if he wanted to give Elena the cure, he would have by now. She dares him to take the ascendant, knowing it could mean a life without Elena. He walks away. Damon goes to see his mother. She tosses the cure box in the fire when he says he didn't bring the ascendant, saying she's doing him a favor. Lily tells Damon the last thing she wants is for him to get to spend eternity with Elena. She tells Elena that Damon was never going to give her the cure. Elena realizes what Damon was getting at asking about her thoughts for five years from now. He confesses to Elena that he didn't stop his mother when she threatened to destroy the cure because he's a "selfish idiot" who doesn't want to lose her. Elena suggests they give it to someone else, but Damon tells Elena she's going to take it -- and so will he.
In I'd Leave My Happy Home For You, Alaric grades papers alone at school at night when he sees a figure streak past the door. Suddenly, someone throws a bag over his head. At the Salvatore house, the bag is removed from Alaric's head and Matt, Damon and Stefan wish him a happy bachelor party in a room filled entirely with hot young girls. Damon tells Alaric his plan to feed on Elena after she becomes human, becoming human himself. Alaric can't believe that Damon hasn't told Stefan yet. Damon texts Elena telling her to meet him on the clock tower. At the top of the clock tower, Elena worries Damon will resent her if he becomes human. They enjoy the perks of being vampires and jump gently down to the ground stories below. Damon asks Elena her favorite parts of being a vampire. He likes the heightened sense and being able to compel people and plant memories. He shows Elena her old house. He tells her he'd give everything up to spend a lifetime with her. He has the cure with him. She admits she wants to take it and he says he's ready. "I love you," she says. "Til death do us part," he says. Elena drinks it. She gets woozy and starts remembering her erased memories of Damon. She remembers their first date, then kissing him on her porch, then everything else wiped away. She pricks her finger and it doesn't heal. Stefan calls Damon to warn him not to take the cure because their mom is on the loose. When Damon gets off the phone, Lily appears and snaps his neck, leaving Elena human and alone with her. Stefan finds Damon and tells him Elena is safe. Stefan is upset at Damon for not telling him about the cure, but they pause their argument to find Lily. She inside the Grill, wallowing in self pity. She doesn't see any point in getting better if she's alone. She grabs a table leg and prepares to stake herself but Stefan pleads with her to stick around for her sons. Lily charges Stefan to attack, but Damon injects her with vervain. Damon finds Elena at home. She remembers every moment in their relationship, including when she asked him to take the cure with her on the island and he walked away. She tells him he needs to think things through. Lily wakes up in the cell in the basement with Enzo waiting outside. She begs to be let out and Stefan arrives. Lily shuns him. Stefan is prepared to wait centuries until she sees him as her son again. She promises him she's going to get her people back, no matter what it takes, and then he'll know devastation.
In I'll Wed You in the Golden Summertime, Stefan drives Damon to a house in the suburbs, one of the ones he lived in during one of his many attempts to turn human. He doesn't think Damon has thought things through, like neighbors and a mortgage. Stefan is trying to give Damon a taste of what it'd be like to be human, complete with nuked TV dinner and stacks of paperwork. Damon will also have to figure out a way to make money. He won't be able to get any from Stefan because if Stefan knows where Damon is, anyone could torture him for information on Damon. Stefan explains that sooner or later word will get out that he's human and all the people who've wronged him will come after him. But Damon has a plan. They'll live above a bar that Damon owns in the Northwest. Stefan calls Elena to check in. She's on her fourth champagne. Stefan explains that, despite Elena's fears, Damon has thought through his life with her. Elena urges Stefan to push Damon and make him see that he wouldn't be happy. Stefan pulls out the big guns, asking Damon what happens if he and Elena break up. He reminds Damon that four years ago, he and Elena were soul mates, too. Stefan gives Damon a glimpse of their future two years in, when Elena comes home late from work with no time for Damon. Then seven years in, when Damon comes drunk from the bar and blames her for not being able to do the things he did as a vampire, saying that becoming human was a mistake. Damon snaps out of the vision and accuses Stefan of trying to change his mind because Stefan doesn't want to lose Damon and Elena. Finally, Stefan points out that Elena is human and could die at any time. He gives Damon a look at his booze-filled, sad and lonely life without Elena. Stefan confesses that this look at his human life was Elena's idea. When Damon asks what he should do, Stefan says Damon has to want to be human for himself. Damon finds Elena her. After Stefan left suburbia, Damon saw an older couple getting out of their car,in the chapel and explains to her that he will take the cure and become human for still flirting and in love and he made up his mind. They finish their literal roll in the hay in the barn and realize how late they are to the ceremony. The ceremony begins. Jo's dad walks her down the aisle. Jo and Alaric wrote their own vows. Damon and Elena picture themselves as Alaric recites his vows to Jo, talking about the many ways they've dodged fate in their lives. Jo begins hers but suddenly starts gasping. Stab wounds appear in her abdomen, then Kai appears. He cripples everyone in the barn with his magic then blows out the window, sending Elena crashing to the floor.
In I'm Thinking Of You All The While, Damon attempts to feed a wounded Elena his blood. Damon worries that Elena won't take his blood and that she won't wake up. Stefan and Caroline awaken, brush the fallen rubble off of themselves before rushing over to find a broken hearted Damon hovering over a lifeless Elena. They suggest that Damon rush Elena to the hospital, and like that, Damon picks up Elena in his arms and using his vamp speed, races over to the hospital. Damon calls Bonnie to tell her Jo is dead and Elena won't wake up. Bonnie tells him that for some reason, Kai drained hers and Matt's blood but left them both alive. They both seem confused. Damon gets a text : "Ty werewolf, Kai vampire". Then Kai shows up with the werewolf bite in his neck. Damon offers to go get the cure in New Orleans (from Klaus) if Kai tells him what he did. Damon finds Bonnie bleeding internally with a collapsed lung. Kai tries to encourage Damon to walk away, to leave Bonnie to die and go live the life he always dreamt of with Elena. Damon apologizes to Bonnie, then kisses her on the forehead, Bonnie attempts to move her head out of the way, then walks away. Kai is outraged Damon gave up on her so easily. But Kai doesn't stay upset long as Damon sneaks up behind him and suddenly takes off his head with one clean swipe of his arm. Damon then rushes to feed his blood to Bonnie whilst stroking her head, comforting her. The next day, everyone regroups at the Salvatore house. Elena is asleep in a coffin. They take turns saying good-bye. Caroline and Bonnie go first. Jeremy arrives and rushes over to his sleeping sister and grabs her hand. Damon and Stefan close Elena's coffin in the crypt. "If word gets out that her body has the cure in it, every vampire will come after her. Bonnie is going to spell it shut." It's Damon's turn to say good-bye. Elena finds Damon lying in the road where they first met. She gets up and start to question Damon and claims that she knows something bad has happened. Elena asks Damon again how bad it is. He tells her what Kai did. She tells him to live his life and enjoy himself. They slow dance in the middle of the road. Stefan sits down with Caroline, and tells her he made a list about all the ways loving her has changed his life. He understands if he has to wait for her, and says he will. "When you're ready for me, I will be ready for you," he says. Damon and Elena finish their dance and Damon prepares to spend the next 60 years of his life without her in it. He sadly kisses her. An unknown amount of time passes. As it appears, Mystic Falls is now a war zone; Matt still looks like he did as he patrols the abandoned streets in his sheriff car and Damon stands on the clock tower, watching over a, seemingly, destroyed Mystic Falls.
In Day One of Twenty-Two Thousand, Give or Take, he, Alaric and Bonnie have been traveling in Europe trying to get over their grief. He saves Bonnie from getting hit by a car even if if she would've died, Elena would be there. Damon arrives back in Mystic Falls and sees that the Heretics have moved into his house. He goes to Bonnie and they talk about how he almost got her hit and that she is his best friend. She tells him that she wants to fight the Heretics and take their town back. After Bonnie is attacked by Malcolm, Damon comes up from behind him and extracts his heart.
In the flash forward of three years, Stefan feeds a desiccated Damon in Brooklyn, New York and tells him to wake up. He tells him he didn't want to be awoken until Elena was. Stefan tells him he needs his help, but arrows and bullets start flying towards them and Damon says she's back and she won't stop until Stefan is dead.
In Never Let Me Go, Damon and Stefan have decided to crash at the Lockwood Mansion. Stefan realizes Damon killed Malcolm and reveals that Lily took Caroline in retaliation of Malcolm's death. Stefan tells him that he's going to over to the house and fix what he's done. Damon is at the house and he tells Lily that he was the one who killed Malcolm, not mentioning that Bonnie was involved. He tries to bargain with her to swap him for Caroline and when he tries to walk in, he wonders why he can't walk in. Lily reveals some papers that the deed was changed and she tells him she has to go bury her son. Damon sees Stefan go over blueprints and tells him that they no longer own the house. He calls Bonnie and she reveals to him that Alaric wants to raise Jo from the dead. He and Stefan talk while waiting for Bonnie's text that her spell worked and when they receive word, Damon takes the front door. Enzo answers the door and they bicker a little bit. Enzo reveals that Lily and the Heretics went to the Salvatore crypt where Elena is and Damon then leaves quickly. Damon arrives at the cemetery and the group appears behind him. Lily tells him that Malcolm was a vital part of the group and how he helped all of them. She reminds him of the time when he broke Lily's grandmother's vase and he wouldn't admit it. Damon tells her that Elena isn't a toy soldier and she tells him Malcolm wasn't a vase. After hearing what they say about Malcolm, Damon then asks what she wants. Damon tells Stefan that Lily wants him out of town for good and away as far as he can, and that Lily has Elena. Damon then says that Lily wants him and Stefan to be mad at each other and they make a plan. Damon says he's going to find the last member of the Heretics and that they're going to negotiate a trade.
In Age of Innocence, Damon, Alaric and Bonnie head to Myrtle Beach to find Oscar and negotiate a swap with Lily. At the Myrtle Beach hotel, they make a plan on how to capture Oscar and they go to his room. Oscar opens the door and recognizes Damon, which leaves him a little confused. It is then revealed that Oscar knows Damon is Lily's son and that he met him at a bar near Gettysburg in July of 1863. Oscar then tells him that Lily just wanted to know that Damon and Stefan were okay and that she did love them. Damon asks Oscar if he can siphon the visions Bonnie saw and they don't tell Lily they saw him. After siphoning, Oscar asks where the Phoenix Stone is and uses magic on them. Damon catches up to Oscar and tells him he does remember him. He then fights with him, while Bonnie uses a pain infliction spell on him and Alaric shoots Oscar with three vervain darts. He calls Lily and tells her he knows about 1863 and that he has Oscar detoxing from vervain. He tells her to give him Elena and she'll Oscar back.
In I Carry Your Heart With Me, The episode starts with a flash forward to three years from when Damon's standing in the Alaric's doorway. Ric says "step behind daddy," to the girls, proving that they're his children. Damon threatens Ric that if Ric doesn't oblige to what he wants to be done, he'll kill someone. And in present Damon getting a phone call from Lily, who asks to see Oscar. Once Damon tells her that he's about to wake Oscar up from a "vervain nap" Lily tells him that once he gets Elena's body back from her, she'll still be asleep and in a box. Damon hangs up the phone and opens the curtain to the room in which he's keeping Oscar's body, and finds that he isn't there. He opens the closet door and finds Oscar's dead body.Stefan and Damon start arguing about how Damon was using Oscar to get back and that the way Stefan sees it, that Elena was in more trouble than ever because of Damon. Damon accuses of Stefan of being on Lily's side, to which Stefan responds that because Damon can't be with Elena, he makes all of his bad decisions about her. The scene ends with Damon telling Stefan that he needs to get rid of Oscar's body and Stefan tells him that he has to get rid of it. Nora and Mary Louise go to the university in which Stefan and Damon are to ask for Oscar back, while they're moving his body. Mary Louise asks for Oscar back and Damon tells her that he just left. Damon tells Nora that he's been binging hence the reason he smells like blood. She walks around breaking things until Damon changes his story, saying that Oscar knocked him out and took off and that he lost his bargaining chip.
In Live Through This, Damon and Stefan corner her and ask to go find Julian with Valerie. They drive down to Myrtle Beach to get Julian,So while Damon tells Valerie every little word that his little brother wrote (and Damon memorized) in his diary about her breaking Stefan’s heart, she tells them about how awful Julian is. She says he once massacred a whole coastline, but Damon says that’s just run-of-the-mill vampirism. We know the real reason, and we know it’s understandable why she wants to set the guy on fire. So she’s going to do exactly that once they finally find his body — yes, as well all suspected and Damon and Stefan are just learning: Julian is dead. Valerie tells the Salvatore brothers that’s the reason Lily needs the Phoenix Stone. and they learn It’s not a stone to bring people back to life; it’s a stone that captures vampire souls.And Damon calls Bonnie so she can tell Alaric about whoever's hanging out in Jo is not Jo. Valerie is trying to kill Julian, but it doesn’t take. And before she can say “incendia” (again), Mary Louise, Nora, Beau, and Lily arrive. Valerie spits out that Lily was the one who gave Kai the idea for the Elena “Sleeping Beauty spell.Damon is so outraged to hear about Lily’s part in Elena’s coffin-ing that he wants to kill her. But once he finds out that Enzo has the Phoenix Stone, which of course he hands over to Lily without question, Damon hopes that Lily brings Julian back. He wants his mother to see the man she’s missed for 100 years and to be able to hold him — so that when Damon rips off Julian’s head in front of her, he'll be breaking her heart, as well. “I want to destroy her,” he says.
In Best Served Cold, three years from present Damon arrives at Rick's home to talk about Caroline, who is now a production manager at a news channel and engaged to Alaric, appears on television bloodied announcing there is a message for Stefan Salvatore. Heretics are ready for a peace party inviting the whole town, which means Stefan and Damon. Damon doesn't want to go. He wants Lily to enjoy her life with Julian — for exactly six months, when maximum happiness has set in, so then he can kill Julian and really hurt his mother. Stefan wants to kill her boyfriend tonight. Damon decides to attend the party simply to stop his brother from killing Julian so that he can kill him himself six months later. Damon prods Stefan repeatedly throughout the party to explain why he needs Julian dead so quickly, but he never gives the full answer… He keeps saying it's not his secret to tell. Matt takes out Damon with his own bourbon: He vervains it and then vervains him even more with a syringe to the neck. With Damon out of the way, Stefan goes to the kitchen to stab Julian and throw him in the fire. But when Lily comes in and saves him, Stefan loses his nerve. Damon comes to just in time to get the fallout from the attempted murder on Julian.
Back at the Lockwood mansion, Stefan finally tells Damon why he's so eager for Julian to die posthaste: He killed his unborn son. Like any good brother would, Damon agrees to help Stefan kill Julian now, and abandon the six-months-from-now plan.
In Mommie Dearest, Stefan invites Lily over so he can calmly remind her that she's shacking up with a psychopath. He tells his mother than he got Valerie pregnant in 1863, and when Julian found out, he got rid of the baby.Lily isn’t buying it. Valerie is a liar. Stefan concedes, pours his mama a drink, and watches as she falls to the floor from a nice glass of concentrated vervain.
Lily wakes up tied up to a chair. Her two sons take turns comparing Julian to their father a man who served a 12-year-old his pet turkey for Thanksgiving dinner. We learn that Giuseppe Salvatore forced Damon to eat poor Sammy. Bring on the nightmares. Over at the Lockwood Mansion, Damon goes back to that awful Thanksgiving night. As if eating your own pet turkey wasn’t bad enough, Giuseppe accused Damon of stealing money. It’s clear that Damon didn’t take it, but he confessed in order to protect Stefan. His punishment? A cigar to the forearm. Current-day Lily looks wounded and defiant at the same time. She claims that she knew Giuseppe was a monster. And then, her neck begins bleeding. Through choking breaths she reminds her boys that she bound herself to Julian. If he dies, she dies.
Damon shoving the miniature sword he snatched from Enzo into Julian's body. He scoffs at the Hamlet Community Theater of it all — his mother linking her life to a boyfriend who engages in a duel with the one guy who pines after her. Enzo didn’t know Lily was linked to Julian. He punches Damon out of anger before Julian cracks Enzo’s neck. Julian stabs Damon; Stefan arrives and cracks Julian's neck. Everyone lives because the “special sword” doesn’t permanently kill vampires. Julian runs to Lily, tattling on Damon for trying to kill him, ergo, trying to kill her. Julian picks up the sword and leaves with his bloody girl. Notice that Julian picked up the sword.it just needs one thing to possess the power against immortal foes — the Phoenix Stone. Without it, the sword is just a blade.
In Hold Me, Thrill Me, Kiss Me, Kill Me, Lily, Damon and Stefan carry out a risky plan to take down Julian which requires Lily and Julian unlinked with the help of heretics. Valerie discloses about Julian to the rest heretics who are now on her side completely except Mary Louise.Damon and Stefan finally corner Julian, but are interrupted by the heretics. Julian forces Lily to choose between killing Valerie, or Damon. Not realizing they are no longer linked, Lily decides to kill herself in order to protect her actual children. The heretics and Stefan bid heartfelt goodbyes to Lily while Damon in his unforgiving self, gives a crisp one "You made your bed. Have a nice nap!"
Rewinding back to the three-year flash forward at the beginning of the episode, Damon is held captive by some woman whom he hallucinates as Lily; he asks for forgiveness as he bid her goodbye in the harshest possible way. At the end of the episode, the unknown woman says that Lily's been dead for years and that Damon will die soon as he has been poisoned with werewolf toxin. She kicks him on his face and the screen goes blank.
In Cold as Ice, Damon, Stefan, Nora and Valerie put Lily to rest. Later, as Christmas rings in the air, Stefan and Damon's search for Julian leads them to a town outside Mystic Falls, they end their search at a bar filled with dead Santa's. After a while, Julian appears and there is a tiff between the brothers and him which later aggravates back home. Later at salvatore boarding house Julian arrives and Damon burning Lily's clothes and asks for Mary Louise which Damon didn't know Stefan had kidnapped and Stefan arrives,The Salvatore brothers-Julian fight finally leads to Damon being staked by the Phoenix stone-dagger and getting trapped inside his hell.
Three years from now in Chicago, Stefan is picking up some stuff from Valerie's place. He burned his Porsche so he has to borrow her car to travel to Dallas to rescue Damon. Nora pushes the dagger inside him, after siphoning out Bonnie's magic. It is shown that Damon is reliving his Civil War days while being trapped in the Phoenix stone.
In Hell Is Other People, Damon's soul is trapped inside the Phoenix Stone, where he's stuck reliving his own personal hell in the middle of the Civil War, with his dead mother wandering around creepily. He wakes up to a groundhog day amidst war and receives a sad letter from Stefan asking him to return. According to higher orders, in order to take leave Damon has to arrest deserters and union sympathizers. So he and his pal Henry, round up deserters — and they end up shooting all of them. Its all weird until Lily shows up and he starts to realize that nothing is real. In the next moment, Bonnie is shown to bring back Damon who wakes up only to realize that his brother is also stuck in the stone and his body has disappeared. Bonnie does a locator spell figuring out that Stefan's body is with Julian. Damon rushes to Julian who's miffed with Damon and thus scorches Stefan's body – Lily shows up again. Damon quickly realizes he's still stuck in hell. He keeps shuttling between the war day and real life on a loop unable to save the deserters. Eventually, Damon is exhausted and under the influence of Stefan, he realizes that he needed his mother the most. Finally, as he returns back to the very first vision of hell he had, he sees Lily. Overwhelmed by emotions, Damon starts sobbing and apologizes to her saying that he missed his mother when he needed her the most and how angry he has been at himself for not bidding her goodbye the way she deserved in the last two chances. He begs her to give him one last chance to serve her and receive her love but death intervenes. Lily dies in his arms and Damon is left devastated.
This time he actually comes back to real life, broken and perplexed, unable to believe that he lost his mother again and begs Bonnie to send him back. As Stefan tries comforting and explaining to him that all of it was hell faux, he loses it completely and goes on an attacking spree over Stefan, Caroline, Matt & Bonnie, killing them all. As the show ends, Damon is mentally & emotionally drained as he staggers to stand still, looking around and realizing that this time... this was real.
In Things We Lost in the Fire, Damon is standing among the bodies of his friends and family. Luckily it doesn’t take him too long to realize this might be real, so he gives blood to the mortals in the room. And just as he's apologizing to Bonnie, Caroline stakes him. When he wakes, he’s chained up in the Lockwood mansion. Damon starts yelling and wakes up his brother from a strange dream. Damon expects to get the regular repent for what you’ve done” speech from his little bro, but Stefan says because of what Damon had to endure in the Hell Stone, he gets a free pass. And then he shares this little tidbit from his own experiences: “Post-hell is much worse. Stefan explains that even once you're free from the Phoenix Stone, its effects bleed into the real world. Stefan is haunted by Damon, and Damon is haunted by Henry. And if the Phoenix Stone effects weren’t enough, Julian has converted Mystic Falls into a haven for the extras of Sons of Anarchy. Damon is not going to like this. When Stefan frees him, they head to a bar, where Julian “welcomes” them. He says that this was Lily's home, now it’s his, he's not going anywhere.Julian has been through this whole Phoenix Stone rebirth before. maybe he has some tips? These two clearly aren’t handling it well on their own.
Damon wanders out of the bar when he sees Henry, but Henry just follows him out. Damon doesn't want to hear what he has to say, though, so he just rips out his heart … and then sees that it's a total stranger. Stefan walks by and gives his characteristic “you should be better” look to his brother. Stefan finally opens up to Damon, explaining to his older brother that he saw him everywhere when he woke up from the Phoenix Stone. He couldn't think of anything except Damon. He was so consumed with it, he didn't even notice Julian taking over the town. He thought the only way to rid himself of Ghost Damon was to burn up the body of Real Damon. So he doused him in gasoline and was about to light him up when Caroline saved them both. It’s a touching story … except he's been telling it to no one a fact he realizes when Julian busts his window with a baseball bat and tells him as much.
Damon calls Tyler, who's back in town for the twins' baby shower, and asks him to see Elena. Tyler says no for a hot second, but then drives him to a nearby shipping yard. Damon pulls Elena's coffin out of the container and opens it, only to find Henry. Tyler tries to shoot Damon, but Damon puts him to sleep instead. Nothing good is going to come of this.
Damon dousing “Henry's” body with gasoline and setting it on fire. Ghost Henry appears behind him, and in that moment, Damon sees he’s burning up Elena’s body, but there’s nothing he can do to stop it.
The next we see him, he's sitting back at the Lockwood Mansion staring into the fireplace. Stefan comes in and asks him where he’s been. Damon explains that he's been dealing with his demons: “My true self is dark.” Stefan explains that his demon is Damon, but that he won’t let him go: “You're also my brother. I'm not going to give up on you. Not now, not ever. ”Damon looks as if he's going to tell Stefan what he did, but instead he just tells him they need to refill their bourbon.
In Postcards from the Edge, old school Damon waiting for a victim flat on his back in the middle of a wooded highway.When a guy named Cooper avoids hitting him, gets out to check on the person in the middle of the road, and asks him what he’s doing there, Damon says, “I don't know. I thought it would make me feel better.” Cooper, give Damon a hug. He just burned up his girlfriend.Cooper can kind of relate: He ran over his girlfriend's cat. Instead of eating him, Damon asks Cooper for a ride. He spills his guts to him, saying how he thinks the lesson of the Phoenix Stone was that he’s always going to be damaged.Damon then says he doesn’t think he can feel for anyone ever again, so he decides to go ahead and eat his ride anyway. Sorry, Cooper, maybe you should have hugged him.
Next Damon Salvatore spiraling-out-of-control tour: picking on the Big Bad. Julian is shooting apples off the heads of his friends, while blindfolded, at the local bar. Damon makes his entrance into the bar by chopping some guys head clean off. Julian's mad… until he realizes that Damon wants to make Julian mad. He puts two and two together, Damon must have lost, or killed, his. Damon finally admits what he did: “I burned her alive.” Julian takes a little bit of credit for this and says he wants to play a game with Damon. Damon dealing with Burning Elena by becoming a member of Julian's fight club. There's only one rule. The rule is losers die. Julian says this raw, physical brutality is the best way for Damon to get over his mental anguish. When Valerie is telling Stefan that his brother has a death wish. She observed it at the bar while she was there telling Julian about the notecard she received from the huntress. And she’s right: Damon makes quick work of his first challenger, so Julian has a better opponent for him: Sam, who has never lost a fight. This fight is tougher for him, and Damon is only able to win because a woman from the crowd throws him a stake to use to kill Sam.
That just pisses Julian off, so he says he's going next. And that's when Stefan comes in to save the day. Valerie tells Stefan about Damon and he takes off. When Valerie returns to the room to tell Caroline, the pregnant lady gets angry. She says that Valerie just wanted Stefan to kill Julian to defend her and prove he still cares about his first love. She sends Valerie to the fight club to help Stefan.
And he needs it. Stefan is trying to talk Damon out of fighting Julian, but no one wants to listen. Julian tells his goons to drag Stefan out of the room, and Damon gets on with the fight.
Julian has 300+ years on Damon, as Julian makes fun of Damon and attempts to rip out his heart, Stefan and Valerie use magic cloaking and headaches to try to get Damon to safety. Only problem is Damon doesn't want to leave. He wants to lay there and die. But he doesn't want his brother to die, Stefan says if Julian killed Damon, Stefan would have to kill Julian, and then Julian's friends would kill Stefan so Damon agrees to go.
Once outside the fight den, Damon tries to wander off. Stefan tells him not to turn off his humanity, and what his brother says surprises him: Damon doesn't want to turn off the switch, he wants to feel the pain. And then he tells him why: "I killed Elena." When Stefan realizes what Damon says, he gives his brother the pain he wants; he punches him over and over and walks away.
Damon is back home, well, the Lockwood home, when the mystery woman who threw him the stake during his fight with Sam walks in. She's brought tequila with her and clearly has one thing in mind. When she kisses him, he pulls back and it’s not just for a second. You can almost see him truly contemplating it.
In This Woman's Work, Enzo calls Damon and threatens that he'll tell Bonnie what Damon did to Elena, if they don’t bring him Rayna's sword. Damon doesn’t want his friend Bonnie who found out about his fling from last week, "Krystal with a K," and was super cool about it to find out about his other, bigger mistake. They go to Bonnie's dorm room, where she pulls out the sword, but she doesn't want to hand it over before Damon tells her what Enzo has on him. "Damon, it's me I'm your best friend," she says. Damon asks her to leave it alone, but she gives him the sword anyway. They take it to Alaric's old classroom, where they find Enzo tied to a chair. Next thing they know, Rayna is there, demanding her sword. When they say no, she shoots Bonnie in the stomach with an arrow. This woman is not very patient. So Damon throws the sword out the window for her to go retrieve.
Damon and Bonnie arrive at the hospital: He takes on Rayna while Bonnie goes to help Valerie with the baby magic-stealers. While Damon is telling Rayna how much she looks like Elena ("You look a lot like my girlfriend and her three doppelgängers") Damon is barely putting up a fight with Rayna; he's ready to go back to hell, but just as she's about to stab him, Stefan steps in front of the blade. It doesn’t go all the way in, but he's been marked and as his moments with Caroline flash before his eyes he realizes he has to get out of town. "I'll see you brother," he says before fleeing. After his brother takes yet another fall for him, Damon is feeling particularly angry, so he goes to take it out on Enzo, who's still tied up in Ric's old classroom (Whitmore). He’s ready to end him when Enzo shouts out what we all knew/suspected: Elena is alive. It turns out that Tyler has been working with a group Enzo is mixed up in. The coffin Damon burned up was empty; the real Elena coffin is safe in New York. Damon calls his brother to give him the good news, but even that can't cheer up Stefan.
In Moonlight on the Bayou, Damon has promised Stefan a way to rid him of Rayna so Damon and Bonnie head to the mysterious Armory where they meet Enzo, who has been working for the Armory for several months to help capture Rayna Cruz. He tells Damon that if they can get Stefan to come to the Armory, Rayna will follow and they can capture her. Damon and Bonnie agree to this so Damon contacts Valerie and tells her of their plan. When Damon mentions "Armory", Valerie warns Damon that it is "a black hole of lies". And once they capture Rayna they'd be happy to let her kill Stefan. Damon goes back into the Armory and tells Enzo that he can't get a hold of Stefan and it's time for him and Bonnie to leave. Enzo knows this means Damon knows exactly where Stefan is and Damon tells that he also knows Enzo allowed him to believe Elena was dead so he'd help him kill Rayna. He tells Enzo they are leaving and are going to come up with a plan "B" just as Enzo shoots Damon with vervain darts and pistol whips Bonnie over the head.
Damon wakes up on a cot with an unconscious Tyler Lockwood on a cot next to him. Tyler has apparently been in a coma since Damon beat him when he hallucinated burning Elena's body. Enzo tells him Tyler also works for the Armory and that it is a full moon, thus the reason for Damon's cellmate. If Damon gives up Stefan's location, Enzo will let him out. Damon tries to break out, but this wakes the sleeping Tyler who starts to transform despite the sedative Damon gave him. Damon calls Stefan who happens to be in New Orleans at a bar with Klaus so Damon ask if there was any chance he could bring home a cure for a werewolf bite. Stefan tells him that he will see what he can do. Meanwhile, Bonnie shoots Enzo with a vervain dart and drags his hand to open the door to find Damon. When she sees the trouble Damon's in she runs back to Enzo and chops off his hand with an ax. She opens the door and Damon and Tyler tumble into the hallway wrestling around while Bonnie tries to hit Tyler with and I.V. pole. Tyler snatches it from her hand and rams it into her causing her to fall back against the wall, hitting her head so hard it bleeds and knocks her unconscious. Damon tells Tyler to get out or he will kill him. Tyler sees Bonnie and runs away. Damon tries to heal her with his blood but nothing happens because Enzo gave her something to mute her magic. Damon picks her up and carries her away.
Next Bonnie is in a hospital bed, still unconscious. Damon is telling her that as soon as the crap that Enzo gave her is out of her system, he will heal her. He tells her that she is a terrible friend for almost dying because he'd have to go through years of guilt and self-loathing. He tells her that since she and Stefan won't stop trying to help him all the time he's going to "take himself out of the equation."
In I Would for You, Damon and Bonnie are still at the hospital. Bonnie's magic is returning again. Damon seems very cheerful as he has a plan for killing Rayna Cruz. He tells Bonnie he will be executing his plan alone, but Bonnie is doubtful that he even knows how to kill her. Enzo has continuously been calling her but Damon refuses to let her answer her phone as he wants her safe.
At Mystic Grill, Rayna, with her sword pointed at a vampire; Matt, with gun pointed at the vampire; and Penny watching, Rayna is instructing them on how to get information out of a vampire. Damon startles her from behind and engages her in witty banter and tells her he has an ally who told him where she was. Matt turns his gun on Rayna and shoots her as Damon vamps over and rips out her heart. Penny is horrified at Matt. Damon gives Matt Rayna's sword and tells him to get rid of it. He also asks Matt where he can get a buzzsaw.
Damon has Rayna's body dismembered and stuffed into several trash bags at the bottom of a well. He casually waits in a lawn chair for her to phoenix back to life. Smoke starts coming out of the well. Once it's cleared, Damon throws down some of Elena's clothes for Rayna saying again "you two look exactly alike". She tells him it is her very nature to kill Stefan after Damon kindly asks her not to. Damon receives a text from Bonnie stating that Rayna's lives are limited and she only has two left. So Damon shoots her down in the well and then buries her so on her last life she will suffocate in the ground. Meanwhile Bonnie learns that when Rayna dies her last death everyone who bears her mark will die too. Damon frantically digs Rayna up and tries giving her blood. He then does mouth to mouth resuscitation and then tries chest compressions. Finally Rayna sits up and coughs up lung full of dirt. Rayna grows stronger with each life and as this is her last life she easily grabs Damon by the throat and throws him across the clearing. They fight in the clearing, Rayna clearly an equal match for Damon; when she is about to stake him several people from the Armory show up and shoot her with two dozen tranquilizer darts before she finally is put down.
Stefan is finally able to come home. Damon tells Stefan that they can't actually kill Rayna and why. Stefan says they need to find a way to get rid of the scar. Damon tells him to get on it and hands him two sealed envelopes. He tells Stefan he's not a good brother when he's not with Elena so he's gonna stay by her side and desiccate until she wakes up. Damon tries to reassure Stefan that it's temporary and they'll see each other again. He walks out the door.
Damon is in New York with Elena's coffin and his. He hears Bonnie's voice behind him say "You weren't even gonna say goodbye." She can't believe he would leave her because if he desiccates until Elena wakes up then she'll never see him again. She says she is not ok with his decision and it's selfish and he does not get to say goodbye. Damon gets in his coffin and desiccates.
Three years later the coffin opens and Stefan is frantically trying wake him and feed him blood. He says he needs him; that his scar opened up that morning. Rayna has caught them both. She tells Stefan there's a way to transfer the mark to Damon since he's the one who deserves it. Stefan asks "You want to pit us against each other?" Damon speaks from behind Rayna saying "Except it wasn't her idea. It was mine."
In Days of Future Past, Damon and Rayna Cruz are still in the news studio trying to convince Stefan, who is all tied up to a chair, to trade his mark over to Damon. Damon is bent over and very sick from the werewolf venom. Finally Stefan says his phone is in his back pocket and Damon can use it to call Valerie to do the transfer spell. As Damon is pretending to get Stefan's phone, he unties Stefan's hands and tells Stefan that he is so full of werewolf toxin that he can't even feel his face. Stefan stands up quickly and shoves Damon halfway across the room and into Rayna, knocking her down. Stefan quickly grabs her sword and speeds away with it. Damon and Rayna fight with each other until Damon chokes her with cables; right before she passes out she's able to grab her vervain dart gun and shoot Damon. They both collapse to the ground, passed out.
Damon wakes up only to find Rayna already awake, suturing her own arm that had been deeply cut. Rayna says she would love to kill Damon first but her target (Stefan) and her sword are on the move. She says her "mystical nature calls". She reminds Damon that if he transfers Stefan's scar to himself and she lives another sixty years or so he'll never see Elena because when Rayna dies, so do all those who carry to the mark. She leaves him there to contemplate all that she has said. The phone rings at the news studio; Damon groans in pain as he struggles to get up to answer it. Stefan is on the other end and tells Damon that Valerie is coming to siphon Damon's werewolf poisoning. Damon tells him to come back to the studio. Stefan doesn't like the idea so Damon tells him to just keep driving. Damon has rigged a way to charge his cell phone and calls Enzo and asks him if he is still friends with those "nut-jobs" from the Armory. Damon tells him he needs to set up a meeting with them. Enzo tells him he knows the perfect spot: the Armory uses an airfield near Dallas.
Damon is sweaty and shaking with fever as Valerie approached and siphons the werewolf venom out of him. She mentions he is healthy now so they can do the transfer spell. Damon quickly jabs Valerie with a vervain dart and she falls asleep instantly.
Damon is driving with Valerie just waking up in the passenger seat. Her hands are tied with vervain-soaked ropes. Damon confronts her about how long she's known about the transfer spell: he thinks she's known all along. Damon accuses her of lying to Stefan; knowing that she could have transferred the scar three years ago but she knew he'd spend it with Caroline. She confesses that she did know all along but the spell requires transferring it to a blood relative. And Damon has spent the last three years in a coffin. Damon tells Valerie that he was a piece of crap before, then he met a girl and she made him good. Stefan calls and Damon says he has a good plan. Stefan says "so you're not taking the scar?!" Damon simply says "I have a plan". Valerie, sitting next to Damon in the car tells him she should never have trusted him. Just then Damon and Valerie hear a shot from a gun through the phone. Rayna gets on the phone and says to Damon "I'll catch you later". Valerie tells Damon that they're too late and blames Damon; Damon says "screw it I'm in". He wants her to give him the scar immediately. Damon and Valerie finally pull up the airport to see Stefan laying on the ground. Valerie says she can bring him back: she's done it before. Damon is wondering aloud where the sword is. Valerie and Damon each blame themselves. Damon reassures Stefan's body that he'll get the stone and make it right.
In I Went to the Woods, Damon sat next to Stefan's body on the blacktop at the airport. Valerie tells Damon that Nora and Mary Louise didn't know that Rayna had stabbed Stefan and his spirit was trapped inside the Phoenix Stone. Damon tells Valerie that they need the get going. Valerie tells Damon that she's not going anywhere with him and that he could have prevented all this by taking Stefan's scar, putting Stefan first for once in his life. Damon tells her that he is trying to make it right. He wants to find Rayna and get Stefan's spirit back in his body. Valerie argues that the stone is destroyed and Stefan's spirit with it. Damon isn't convinced but she continues to insist that logic and a sense of reason dictate that since the Stone was destroyed so was Stefan. Damon tells Valerie that if Stefan is truly gone, he will feel a tremendous amount of responsibility, and spend and eternity haunted and will see his own self-loathing reflected back at him in everyone's eyes. He's not ready for those kind of things. Therefore, Stefan isn't dead. He begs Valerie to try things his way: it's less depressing. Damon suggests that Valerie do a locator spell to help him find Rayna. Valerie walks away saying she's going to do exactly what Damon suggested, only she's going to do it on her own. She mutters "invisique", turning herself invisible so Damon cannot follow her.
Damon goes back to where they left Stefan's body only to find it gone. He calls Valerie while while driving slowly through town and gets her voicemail. He starts to questions her voicemail about why she took Stefan's body when he sees "Stefan" walking toward him.
Damon and "Stefan" go out to dinner where "Stefan" isn't at all shy about being a vampire: he bites right into the waitress' wrist. Damon eyes him carefully and gets up from the table and makes a call to Alaric asking him "when did you realize Jo wasn't Jo?" Valerie is with Alaric and she tells him that Damon needs to keep "Stefan" close as they will need his body. Alaric tells Damon that that is not Stefan. Furthermore, if the real Stefan is in a human body, he has about three days to live. Alaric and Valerie piece together that the real Stefan is living inside a body wanted by the police: a Marty Hammond in Arkansas.
Damon gets off the phone and sees that "Stefan" has exsanguinated everyone in the bar. They leave and as Damon drives, "Stefan" reads Stefan's journals, making snide comments and pretends to actually be Stefan. Damon tells him to give up the act, as he knows he isn't Stefan. "Stefan" says that he had to try and that he never plans to give back the body. "Stefan" rolls down the window and chit chats with Damon for a minute, asking how far away Memphis is. Then he bails out of the car through the open window. Damon screeches to a halt but cannot find him anywhere. Damon calls Ric to tell him what happened.
Damon goes to a police station and puts on an officer's coat, and pretends to be Matt Donovan. An officer tells him they raided a cabin where "Marty Hammond" had been staying at, but it looked as though he had left. With the snow storm rolling in, there's no way he'll survive the night in the woods with these temperatures. A woman comes in to the police station saying that she saw Marty Hammond and he attacked her. Damon tells the officer that he'd like to question her. She tells him exactly where she saw "Marty". Damon tells the rest of the cops to head the opposite direction. The woman also tells Damon that she dropped her cell phone on the ground when "Marty" supposedly attacked her. Damon calls her number and Stefan is so relieved to hear Damon's voice on the other end. Damon is already on his way to get Stefan. He tells Damon that he his legs are totally numb and he can't tell if his tremors are from withdrawal or hypothermia. Damon tells him to get up: this is not how Stefan Salvatore dies! Stefan tells him that he sucks at playing the hero. Stefan is finally able to stand and start walking. Stefan asks Damon if he remembers playing hide-and-go-seek when they were young. They reminisce for a minute until Damon asks him why he asked about hide-and-go-seek in the first place. Stefan replies "Because you're never gonna find me". He then collapses into the snow, in the middle of the road. Damon pulls up seconds late and carries him to the car. When Stefan wakes up, Damon gives him donuts and Stefan eats greedily until his nose starts to drip blood onto the donuts.
Damon tells him that they have less than forty-eight hours to find his real body since human bodies cannot sustain vampire spirits.
In One Way or Another, Damon and Stefan (who is still trapped inside Marty Hammond's body) are in the car. Marty's body is deteriorating rapidly. Damon encourages him to stay alive by sitting back, relaxing, and finding his happy place. But Stefan continues to vomit blood into a bag. Damon dials 911 to get an ambulance to come to them. Alaric also meets up with them. Damon had planned on Valerie arriving with Alaric so they could do a soul-swap. Damon sees that Alaric has come without Valerie and says "where's my witch?". Alaric tells Damon that Valerie was able to do a locator spell on the vampire inside Stefan's body. His name is Ambrose and he is hiding out in a frat house by Memphis College. Alaric recommends that Damon stay with his brother and say his good-byes; Damon gets mad that he would suggest such a thing when they could be out, saving Stefan's life. Damon and Ric head to Memphis College. On the way there, Damon fishes for information regarding his best friend: Bonnie Bennett. Damon apologizes to Alaric for not saying good-bye in person before his three year nap.
Damon breaks down the door to the fraternity house where all the frat boys were encouraging Ambrose to chug on someone's neck until they died. Damon cannot enter the house, as he's not invited in. He runs back to the car and tells Ric that he's up. But Ric isn't as enthusiastic as he once was. Damon tells him that he is "still in the game", he can tell because Ric pointed a rifle at him when he knocked on his door. A girl knocks on Damon's window with a cell phone in her hand. She says that if Damon doesn't answer the phone she's supposed to run into traffic.
Damon talks to Ambrose. Ambrose tells him he doesn't care much for the taste of blood. He likes the mind games, the eavesdropping, killing college kids; but making them kill each other is his favorite. Ambrose proposes a deal. He wants Rayna Cruz dead. She made his life a living hell. Ambrose says he'd be willing to jump into the body of a transitioning vampire and he'd gladly give Stefan's body back. All Damon has to do is find a witch who can soul-swap him.
Damon and Alaric find the taxi Rayna was in. The driver seems very rattled and afraid. He had been compelled to stay where he was. He tells Damon that some guy with an accent shot at the car and dragged his passenger away. Damon immediately calls Enzo and tells him to bring Rayna back. Enzo plays dumb and then he asks Damon how Bonnie is. Damon tells him they aren't talking about Bonnie they are talking about Stefan who is currently dying. Enzo suggests they find another way to save him because they aren't getting Rayna.
Alaric explains to Damon that Bonnie and Enzo are in a romantic relationship together. Ambrose calls Damon while him and Ric are on the road. Ambrose tells Damon that "modern Greek life is even less dignified than it once was". Damon tells him about the snag in their plan.
Damon and Alaric arrive at the frat house to see a girl, with blood all over her and carrying a broken beer bottle who does not look at them when they call out to her. Damon and Ric head to the doorway of the frat house and this time Damon is able to enter without being invited in. Everybody is dead inside. Damon tries to call Ambrose; the phone rings next to a body on the floor. Alaric gets the idea that perhaps Ambrose heard Damon say where they were taking "Marty". Damon calls the EMT and finds out that they are just meandering along on their way to the motel to meet Valerie. Damon yells at them to drive as fast as they can with their lights on. Just then there is a crash.
Stefan is hiding from Ambrose in a house that Ambrose can't get into. Ambrose rolls into the house an open tank of gas and as he throws the flame toward the house, Damon shows up on the porch and catches the flame. Damon says "Fun's over". Ambrose retorts "On the contrary. Fun's just begun". He splits a piece of wood in two, forming a stake. He's about to throw it at Damon when he is shot from behind with a vervain dart by Alaric, who states "I hate how good that felt". Damon gets a smug grin on his face: his old buddy is back.
Damon and Alaric get both Ambrose in Stefan's body, and Stefan in Marty's body to the motel for Valerie to perform the spell. Damon makes her promise she can do the spell. She promises. During the spell Valerie gets weak and starts to bleed from her nose. Damon catches her as she falls, demanding that she finish the spell despite Alaric's protests that she isn't strong enough. Valerie continues. Stefan awakens, in his own body.
Alaric storms out the door with Damon on his heels. Alaric tells him he wants to go home. Damon is full of apologies for abandoning him. He begs Alaric to tell him what he needs to do to make amends. Alaric tells him that the last three years of his life have been the best ever for several reasons but the last reason is: Damon wasn't there to barge in and screw things up. Alaric does not want things to go back to the way they were like Damon does. Damon thanked him for his honesty. Just before he leaves, Alaric tells Damon where to find Bonnie: undercover at a psych ward. Damon stands at the door to Bonnie's room in the psych ward with a bouquet of flowers. Enzo has just delivered some terrible news to Bonnie and they are embracing. Damon says "Bonnie" quietly. She walks toward him with tears falling down her cheeks only to slam the door in his face.
In Somebody That I Used to Know, Damon goes to see Bonnie again, flowers in hand. This time Bonnie and Enzo are packing. Damon says to them "I have an idea".
Enzo takes Bonnie to a small cabin and Damon follows them. He tells Enzo that he can see why Enzo likes it: it's lonely, cramped, and like a prison cell. Damon enters the cabin and remarks on its coziness and on how it's a big step to move in together. Enzo takes Damon down to the storm cellar where Rayna has been kept. They find her scribbling on scraps of paper that cover the floor. Enzo explains to Damon that Rayna's brain is full of visions and that she is still connected to all of the vampires who escaped when the Phoenix Stone was destroyed.
Damon has an idea an tells Rayna that Enzo and he would be a hit squad for all the vampires left on her list because they want her to die. Since she's on her last life, and is sick of living, they would take her life and transfer it to Bonnie, who is dying. Rayna isn't sure it'll work; however, Bonnie who is schooled in the kind of thing thinks that it will. She tells them that they need to prove that they can kill the vampires on her list so she can clear her head. Damon asks for the list and Rayna hands him a stack of messy papers. She tells them that those vampires could be anywhere and they better get started since the anti-magic pills in Bonnie's system will wear off within forty-eight hours. The Armory will then be able to track her again.
Damon calls Rayna while they're on the road for instructions. She wants them to head back toward Texas. That's where the Hell Stone was destroyed so all the souls blasted outward from there. She says their next target is in Richmond, inside a bright clean room. Damon sarcastically replies "Oh yeah. I know exactly where that is". Then Rayna says she's seeing a lot of teeth.
They catch the vampire at a dentist's office. It takes Bonnie, Enzo and Damon to take him down. Ultimately, it's Damon who chops the vampire's head off. Damon realizes how much work this is going to be so he calls Stefan and asks him if he can get his hands on a vamp arsenal and that needs backup. He tells him that Bonnie is in trouble. Stefan tells Damon that he's with Ric and asks what they can do.
Damon, Bonnie and Enzo go after vampire, after vampire. After shooting a couple vamps through the heart Bonnie remarks to Damon "I just picture your face as the target".
Alex tracks Enzo down to a furniture warehouse. Damon and Bonnie overhear part of the conversation before Damon grabs Bonnie and vamps her to safety and they drive away. As they are driving, Damon tries to comfort Bonnie by telling her that Enzo can take care of himself. Bonnie says she tired and doesn't want to talk to him. She's worried about Enzo so he needs to stop trying so hard. Just then Enzo calls Bonnie. While she's on the phone, Damon noticed a huge sore appearing on the back of Bonnie's left hand. Bonnie asks Enzo how much time she has after the first scab appears. Damon hears Enzo say "A week, maybe less". Stefan calls to inquire as to Bonnie's health and Damon tells him.
Rayna calls with more leads. They arrive at a restaurant and begin killing all the vampires when one says "Lorenzo! Don't! I'm a friend!" Enzo doesn't recognize him and apologizes for that fact. The vampire says "It's me, Beau!", one of the heretics who, in his natural body couldn't speak due to Rayna's scar. Damon wants to kill him. Bonnie wants to save him because he helped save Caroline's life and the lives of her children. Damon vamps over to Beau and rips his heart out.
Damon and Enzo get into an argument in the parking lot. Damon reminds him that sparing Beau's life would've been a deal breaker with Rayna. He goes on to say he does things others don't want to do. He reminds Enzo that he gave his girlfriend pills that will kill her. Enzo just keeps his cool as always and reminds Damon that he just goes and lies down in a coffin, hoping that when he woke up all the messes he made will have been cleaned up. Damon grabs Enzo by the neck and explains that he chose to desiccate because he didn't want to hurt his friends and that he is holding Enzo personally responsible if anything happens to Bonnie.
Bonnie interrupts them saying "DAMON"! Enzo storms off. Damon admits to Bonnie that he shouldn't have run away three years ago. Bonnie whispers back to him "But you did". She tells Damon that she got over it. He remarks on how she still carries the letter he sent her. She says she keeps it as a reminder not to trust the wrong people. Bonnie tells Damon how Enzo has been there for her every day: hiding her, protecting her. Damon yells "Poisoning you"!
Back at the cabin, Damon goes to Rayna to get another name for the list. He calls Stefan about how Rayna was going to add a few more names to the list. While he is on the phone he is seeing Rayna passed out and the floor and walls are covered with new names.
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In Hello, Brother, the episode opens much like the first episode of season one with a couple chit chatting, driving through the fog when they have to swerve to avoid hitting Damon but they actually do hit Enzo. The couple sneak over to check on Enzo when Damon starts clapping from behind them, leaning against their car. Damon tells them it's a slow night as Enzo sits and pops his broken bones back into place. The two vampires drive the couple to an old slaughterhouse.
Damon and Enzo chat about how they are serfs, slaves or lackeys who are being mind controlled. And their job is to bring the worst of humanity to the slaughterhouse. Damon makes each of them tell him what the worst thing they have ever done was. The man is the winner so the woman gets a quick death by Enzo, feeding on her. He then takes he body to dispose of it while Damon takes the man into the main part of the slaughterhouse where many pieces of humans are hanging all around. Damon takes him to where they are standing over a grate. Below the grate is a pool of blood. Damon jabs a giant hook into the man's back; he screams out in pain. Damon pushes some buttons that lift the man up, open the grate and dips him down into the blood. The hook comes back up with only a small piece of the man remaining.
Later, Damon is kicked back in a lounge chair reading "Fifty Shades of Grey" by the bloody pool without the grate. Enzo asks Damon how many more bodies does that "thing" need?! Damon reminds him that it can hear him. Enzo asks Damon if he has any control of his own mind left. Damon tells him that he has flipped his humanity switch. Enzo yells at the bloody pool that has started to bubble "I'm sorry, did we wake you? When does this end"?! He wants to know how many more bodies until its full. Damon then kicks Enzo into the bloody pool. The monster grabs his face with clawed hands and pulls him back under. He is then released and able to climb out. Damon asks him if he got an answer.
Stefan finds the slaughterhouse where Damon sees him and says "hello brother". Damon starts mopping the floor and tells Stefan that he's doing daily chores. Stefan asks him what has a hold on him and what was in that vault? Damon says that it doesn't matter; only that he's been killing bad people. Damon tells Stefan to go home. Stefan observes out loud that Damon has flipped his switch and that he can help him flip it back. Damon tells him that he's seen how this ends and his humanity can't save him from it. He tells Stefan that he's talking about hell; he's seen it, tasted it, touched it. Stefan tells him that he's not making any sense. Damon replies with an "okay". Damon tells Stefan that he needs to go because "it" doesn't want him yet. Stefan says "not without you".
Bonnie finds her way to the slaughterhouse just as Damon says that Elena doesn't matter to him anymore. That he hasn't just flipped his switch, he's ripped it off the wall. Every bad decision he's ever made sealed his fate. His path and Elena's are not the same. He tells Stefan again to go but Stefan snaps a mop in two and stabs it through Damon's body, making him fall down. Bonnie approached and tells Stefan to get him in the car while she finds Enzo. When Stefan looks back Damon is gone and Enzo mouths the word "go" to Stefan, showing he still has his humanity. Enzo then fakes being emotionless toward Bonnie and they leave unharmed.
Damon and Enzo go to and art show where they confront and artist who painted entirely with blood. The artist whispers in Enzo's ear what he did with the victim that he got all the blood from for his art piece. As they leave with the artist, Damon tells Enzo that he might want to consider flipping his switch so "it" can't hurt those he cares about.
Damon and Enzo take their latest victim to feed the monster. When out of the bloody grate climbs a woman, who is singing to them without opening her mouth.
In Today Will Be Different, Damon chats with a businessman about guns. Damon tells him that he is going to bring him to his buyer as she will find him irresistible. Damon takes him to meet Sybil who is swimming in a pool and she begins to sing to the man. The man starts walking down into the pool toward her. Sybil asks Damon if he enjoys this and Damon answers in a bored tone "I don't know. You're the psychic, you tell me". She tells him she needs Enzo to be like him: all in. She then drowns the man.
Later, Damon is catching a nap in a lawn chair and dreams of when he first met Elena. He watches himself like a spectator as he calls her "Katherine". Sybil then yells at him to wake up.
Damon and Enzo sit on a park bench while out on a hunt for Sybil when Damon suggests a game of twenty questions. Damon describes Enzo to a tee. Enzo tells him that that isn't how you play twenty questions but what Damon is tying to do is get Enzo to realize that while he is here, looking for Sarah Nelson aka Sarah Salvatore, he isn't having any fun. Enzo tells him he doesn't understand what the "boss lady" is up to; why she's pushing pause on her master plan. Damon tells him that her new priority is to give Enzo a spanking, to get him to flip his switch. Damon confesses that he's not so much afraid of Sybil as he is of the eternal damnation she showed them when she got into their heads. Enzo insists those were just mind games and none of it was real. Just then, Sarah Nelson walks toward them on the sidewalk. They pull her aside and down to the parking garage where she jabs Damon with a vervain dart.
Damon rushes up behind Caroline, who has been talking to her kids on the phone in the hallway of Sarah's apartment. Damon removes her daylight ring, throwing it down the sunlit hallway along with her phone which he smashes.
Damon jumps through Sarah's window where her and Stefan are talking. Damon grabs her, wrapping his arms around her head, with a murderous look on his face. Stefan pleads "Damon don't"! He quickly explains to Damon who she is but Damon thinks it's impossible. Stefan tells him that Sarah isn't on his list of sins; he didn't kill her in utero. Stefan tells him that letting her go is what Elena would want. Damon lets her go, telling her to run. As soon as Sarah opens the door to escape, Sybil is there blocking her way and she stabs Sarah in the abdomen. Stefen vamps over to Sybil and breaks her neck the goes to give Sarah his blood but just before he gets to Sarah, Sybil whispers in his ear "I'm a lot tougher than I look". She makes it so Stefan cannot move then she asks "So, who's Elena?"
Sybil reprimands Damon, as it he did not kill Sarah. She wants to know how he is disobeying her. It takes a shred of humanity to defy her. She reaches inside his mind and sees Elena. She sifts through every memory of Damon and Elena; she replace Elena with herself. Meanwhile, Sarah is still bleeding out on the floor and she dies. Damon is completely devoted to Sybil.
Back at the swimming pool, Damon is feeding off a victim's wrist while Sybil makes out with the victim who appears to be dead. Damon rushes over to Enzo and thrusts his hand into Enzo's chest, grabbing his heart. While Enzo is weak, Sybil gets a peak into his mind.
In You Decided That I Was Worth Saving, Damon and Sybil are bystanders at the Gilbert car accident on Wickery Bridge. It's revealed that he's reliving a past memory though Sybil has changed the memory so that Elena has died too. Altering his memory results in Damon telling Sybil that he had never met Elena.
Back at the hotel, Sybil is having trouble unlocking Enzo's mind. She encourages him to be more like Damon who looks quite content, sitting in a chair reading Fifty Shades Darker. Damon suggest they kill Enzo as he has a high tolerance for torture. Sybil says they are moving onto to Bonnie; Ezno assures her that Bonnie means nothing to him. Sybil asks Damon to kill Bonnie, which he has no problem with.
Damon interrupts Caroline's wedding dress shopping with Bonnie by killing the attendant and catching the practice bouquet toss. Caroline tells Bonnie to run and tries to attack him but Damon grabs Caroline around the throat as he realizes Stefan's getting married. He tells Caroline to consider this his R.S.V.P. and throws her across the room. He hunts Bonnie down but she fights back allowing Caroling time to stab a wooden pole deep through his stomach, pinning him into the adjacent wall, allowing time for the girls to flee.
Enzo and Sybil track him down and as Enzo removes the pole from Damon, Sybil is admiring herself in the mirror with a wedding dress held up to her. She says to Damon "So you got beat up by a girl." Damon explains that there were two girls which makes Enzo laugh. This makes him susceptible to Sybil's interrogation methods and she is finally able to see what Bonnie means to him. Since Damon doesn't fight her, she looks for Bonnie in his mind and finds their friendship. She replaces Bonnie with herself.
Damon calls Stefan from the high school and tells Stefan he needs a favor. He says that whatever desire he has to save him, he needs it right now. Stefan finds him sitting on a picnic table outside the high school. He tells Damon that if this is a trap he might as well spring it. Damon assures him that he just needs his help but can't tell him what he needs help with. He tells him that Sybil has LoJacked his brain and when he tries to form the words to tell Stefan it just comes out as "applesauce penguin." He opens the trunk of his car to reveal a knocked out and tied up Enzo.
Damon and Enzo are compelled to fight each other to the death when the clock strikes three. Damon brought Stefan as backup to help him kill Enzo. Damon and Enzo argue about their friendship. Stefan tells Damon that if Enzo can fight this, he should be able to also. Stefan tries to reason with him on all points. Enzo tells Stefan it isn't going to do any good because Sybil has been toying with his brain.
When the clock strikes three Damon and Enzo go for each other. Stefan puts himself in the middle, pushing them apart. They continuously push him out. Damon gets himself in a position where wooden handle is piercing through his back and Enzo is dangerously close to staking him. Damon calls to Stefan for help and Stefan throws Enzo off. Stefan is about to chop Enzo's head off with a shovel when Caroline stops him saying she promised Bonnie. Damon snaps her neck and Enzo snaps Stefan's. Enzo goes after Damon with a saw while Damon can almost reach Enzo's chest. They fall and Damon plunges his hand inside Enzo's chest. Bonnie enters and pleads with Damon not to do this. Sybil shows up behind her and tells her to choose which one to save. Bonnie chooses Enzo. Sybil tells Damon to remove his hand from Enzo's chest.
Sybil tells everyone that no one has asked her what she wants. Damon is an asset. Enzo is a burden. Sybil tells Bonnie that she chose wrong so she's going to have Damon kill Bonni