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.

Damon claims his first two victims at the very opening of the Pilot, 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.

During the episode 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. This story arc continues 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.

Damon first appears in 162 Candles 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.

Damon begins Bloodlines 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 Jonathan 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 suggest 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 visiting 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.

Damon’s first appearance in Let The Right One In is in 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. This continues 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 the season finale, 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.

Directly following the events of the season one finale, Founder's Day, 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 Bennett 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 moon stone 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 wolfs bane 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 wolfs bane so he can tell if she’s a werewolf.) She doesn’t fall for it, able to smell the wolfs bane 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. This story continues 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's 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 Jer’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 Jer’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.” Jer 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. She loved 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.

In Down 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's 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.

And then did it. 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 -- again, despite the fact that she told April that Jeremy was dead way before the fire actually “killed him.” 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 we watched them 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 Casa 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. Again I say, "I don't care how bad you are" isn't the same as "I accept how bad you are," which is what Damon is after. Next time we saw them, they were in his car on their way to New York City.

In Because 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. The flashback continued, and we found out 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. He knew what she was doing all along, because he’d invented that game. In the flashback, we saw Lexi wake up and almost burn. Damon had made sure the door wouldn’t open, so she’d have to stay there, hidden in the doorway all day, while he could make his escape. The difference between him and Stefan is simple, he said: “He’s a victim, I choose to be this way.”In present day, 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.

In American Gothic, an off-screen Sheriff Forbes proved efficient this episode: She tracked down Damon’s car after Katherine 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 PA 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’s 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 shows Elena 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,