In the 1950s, Damon was captured and tortured by the Whitmore family, of which the members experiment on vampires for a "bigger purpose" and during his 5 years of captivity, he meets another prisoner, Enzo, whom he becomes good friends with. Eventually, the plan the two made failed at a critical moment and thinking Enzo "died" because of him, Damon ‘turned off’ his humanity to suppress the guilt and sadness. He sought revenge, an act of hunting down every member over generations which he finally ends with Aaron Whitmore's death.
Damon's sole purpose in coming back to Mystic Falls was to free Katherine Pierce, the vampire who turned him and the woman he deeply loved. After realizing that Katherine never loved him, his love for her fades as his friendship with Elena, Katherine's descendant and doppelgänger, grows. Due to her impact on him and the strengthening relationship with his brother, they begin working together and protect Elena, her friends and family. He currently lives with his brother, ex-girlfriend Elena (when she isn't away at college), and her brother Jeremy Gilbert in the Salvatore Boarding House.
Throughout the series, his bond with Elena continuously grows and they eventually fall in love with each other. Shortly after her death and subsequent transition into a vampire, Elena's feelings for Damon are heightened which makes her admit her love for him and they start a romantic relationship.
In Season Five, he discovers Enzo's undead status and they become friends once again however once "Elena" breaks up with him, he puts an end to his diabolical plan against the Whitmore Family and is then injected with a dangerous compound by Wes Maxfield, causing him to become an Augustine Vampire and the only one in existence.
Damon was born to Giuseppe Salvatore and an unnamed mother on June 28th, 1840 in the small town of Mystic Falls, Virginia. His younger brother Stefan Salvatore is six years younger than him, and the two were very close. He joined the Confederate Army at some point, coming back when he was on leave to spend time at the Salvatore Estate. It is unclear when Damon first met Katherine Pierce, but he left the Confederacy and returned to Mystic Falls to spend more time with her. His father disapproved of what he considered Damon's poor sense of duty.
It is uncertain how or when Damon found out that Katherine was a vampire, but unlike Stefan he did not fear or reject her, and willingly drank her blood. She once demonstrated to him one of her tricks for securing victims: lying in the middle of a road to stop any travelers that may come to pass. Though he showed an initial hesitance, Damon even kissed her while a victim's blood still stained her lips.
Damon wanted to give up his human life and spend an eternity with Katherine, and he begged Stefan to keep the secret from their father, who was a member of the Town Council and a vampire-hater. When Stefan inadvertently revealed that Katherine was a vampire, she was taken away by the townspeople. Their father was furious and scolded Damon for trying to conceal her secret and protect her. Damon was furious with Stefan, but Stefan agreed to work with him to rescue her. In the midst of their daring plan, they were both shot and killed by Giuseppe, who was ashamed of his sons for sympathizing with and loving a vampire. They both died with Katherine's blood in their systems, but Damon awakened first and witnessed the burning of Fell's Church, where the townspeople had imprisoned the vampires, including Katherine.
When Stefan awoke the next morning, Damon told him that Katherine's death meant his reason for living was gone, and he wouldn't complete his transition into a vampire. Later that day, when Stefan returned after being unable to resist feeding on his own father, and inadvertently completing the transition, he forced Damon to drink from a young woman's neck, causing Damon to also complete his transition. He promised Stefan an eternity of misery, not for making him turn but for the fact that Katherine had turned Stefan as well, instead of just Damon. At some point Damon received a daylight ring from Emily Bennett. She told Damon that she had spared the vampires in the church, which Damon kept secret from Stefan until 145 years later, when he would be able to free Katherine from the church.
Damon saw Stefan in 1912 for the first time since they transitioned; both had returned to Mystic Falls for their nephew's funeral. After an initial hesitance, Damon agreed to have a drink with Stefan and catch up. When he was feeding on a human alone, the vampire Sage found him and commented on his lack of enjoyment for the feed. Damon seemed content to feed just enough to survive, but Sage encouraged him to enjoy it, to take pleasure in being a vampire. Once he was persuaded, he tried to get Stefan to enjoy the feed, and talked him into feeding on human blood again. Stefan fed so hard on his victim that he tore her head off, shocking both brothers. Furious with Damon for making him drink human blood, he ran off and Damon did not pursue him.
Damon was living in New Orleans with a vampire he had turned named Charlotte. Damon soon noticed a pattern of strange behavior from the woman, in that every order he gave her, even seemingly innocuous ones, she followed with frightening enthusiasm. He sought guidance from the witch Valerie LaMarche to break the sire bond between him and Charlotte, and the witch told him she needed a human sacrifice of 12 people to do the spell. Damon killed the 12 people, but could not find Val to perform the spell he needed. He ended up ordering Charlotte to count every brick on every building in New Orleans and meet him at the corner of Bourbon and Dumaine. He left New Orleans soon after...
Stefan and Lexi found Damon while he was in New Orleans. At Lexi's insistence, Stefan sought to make peace with his brother before shipping out to the North African front of the war. After an initial hesitance, Damon seemed happy to reunite with his brother after thirty years apart, and the two spent the evening talking. Damon even suggested he might join Stefan and leave for war with him, but Lexi made it clear she did not approve of the idea. Her concerns seemed warranted especially after Charlotte brought a bleeding victim to the bar where they were talking and Stefan started to lose it at the sight and smell of human blood. Later, Damon was all ready to ship out with Stefan when Lexi talked him out of it, citing his profligate lifestyle and how Damon's behavior would not be good for Stefan's rehabilitation. Realizing she might be right, Damon decided not to go, and he left the train station without explaining to Stefan.
1953 - 1958
In 1953 Damon was lured to Mystic Falls by Joseph Salvatore, he injected him with vervain and Damon killed him. Dr.Whitmore entered the room and injected him with another dose of vervain. When he woke up he was strapped to a table and Dr. Whitmore cut one of his eyes out, in order to experiment with his healing factor. Damon was brought to a cell and in the cell next to him was another vampire named Enzo. The two vampires bonded and it was Enzo's friendship that allowed Damon to hold on to his humanity. Dr. Whitmore continued to torture and preform experiments on him and he called him 21051.
Every year Whitmore would show the rest of Augustine Damon and Enzo and demonstrate his research on the annual New Years Party. Enzo then came up with a plan for one of them two would drink the others blood ration in order to build up his strength until the coming New Years Eve. Damon was the lucky one and when the next New Years Eve Party came he broke free from his chains and he slaughtered every member of Augustine while the building set ablaze. Enzo was still trapped in his cage and Damon tried to free him, but the cage bars were soaked with vervain and couldn't get him out. Damon knew that if he was going to save himself he had to stop caring about Enzo so he turned his humanity switch of. Now not caring he left Enzo to burn alive. After finally being free from five years of torture, Damon kept the promise he made to Enzo to kill every member in the Whitmore family, but one and let that person have a family and kill them to but one and to the same thing again and again. Damon did exactly that and among the ones he killed was Aaron Whitmore's parents and Aaron was among the ones that he kept alive.
Damon lived in New York City during the 70s, where he maintained a wild life full of parties and feeding off of people. At the time, he still had his humanity switch off and he killed locals of New York; a soon to be fed upon victim asked if he was the Son of Sam, to which Damon replied, "Son of Giuseppe, but close enough". Damon was friends with Will, another vampire, who ran a bar and let Damon feed on the people there, while in exchange, Damon stole his victim's ID's for him.
Lexi had eventually found Damon and told him that she and Stefan had heard all about Damon's current life and that Stefan was worried for him. Lexi tried to help Damon get his humanity back, but Damon rejected her offer. However, Lexi was stubborn and she stuck with Damon for the following six months. She had gotten Damon to talk about Katherine Pierce, thinking that if he talks about her, his switch will flip on. Damon tricks Lexi into thinking that his humanity was back and the two have a night full of wild sex.
The next morning, Lexi woke up on a roof because the sunlight was burning her skin. She tried to escape by opening the door to get into Billy's, but it was locked. Then she found out the truth: Damon had tricked her. Damon told her that it was his way of getting back at her for annoying him for the past six months. He ditched Lexi on the roof thereafter, leaving her trapped until nightfall. It was revealed in The Cell, that Damon turned off his humanity in 1950's because he couldn't deal with the pain of leaving Enzo behind while escaping from the Augustine Society.
Damon and Elena have spent all summer being together. While Elena was heading to Whitmore College, Damon promises her he will take care of Jeremy. When Katherine shows up and begs him to protect her as she feels someone is after her. When she picks up the phone and pretends to be Elena, she tells Damon Jeremy's issues at school. Luckily for Jeremy, Damon is able to compel the principal to lower the charges to a three-day suspension. Unfortunately for them they soon realize they have bigger problems.
Silas walks into the bar as Stefan and greets Damon. He sits and talks but is only there to read Damon's mind. After getting the information he wants, he says bye to Damon, pats Jeremy on the back, and then heads to Salvatore Boarding House. Jeremy and Damon arrive just in time and Damon instructs Jeremy to take Katherine somewhere and not tell him. This leaves Silas to give Damon a crash course on why he looks like Stefan and to tell Damon what he did with Stefan. This leads Damon to call Jeremy and explain he's had a change of heart. Later, Jeremy is on the precipice of death. Damon finds is able to get to him in time, feed him vampire blood and hold him until he comes back to life. And Damon doesn't tell Elena anything that happened.
In True Lies, Damon is trying to find Stefan with the help of Sheriff Forbes. Later he is talking to Elena on phone when she sees Silas (who she thinks is Stefan) on campus. Damon tries to tell Elena that it isn't Stefan but she is compelled to hang up by Silas. Damon quickly hurries to Whitmore and visits Caroline and tells her that Silas is with Elena posing as Stefan, Caroline tells him about the nagging pit that Elena has about Stefan and he tells her that they have to go look for Elena.
Elena and Jesse are talking when Damon arrives and knocks out Jesse. Elena takes him to her dorm room, seduced him in order to tie him to a chair and ready for the kill but Damon figured out that Silas used his mind control power over Elena so he tried his best to make Elena resist the "rage" by thinking about her worries of Stefan. Later, Damon showed her that he'd snagged Stefan's daylight ring back from Silas the day before. And then Damon said he's secure enough in their relationship that her having psychic dreams about her ex-boyfriend doesn't bother him, but it still sucks. They kissed, and Elena told Damon they were going to save Stefan and she would still love him. Then they passionately kissed.
In Original Sin, Damon and Elena along with Katherine go in search for Stefan when Elena and Katherine both have a same nightmare about him. While traveling Katherine taunts Elena and Damon about their relationship,annoying them both. After reaching Jo's bar,the place which appeared in their dream, Elena and Damon happily leave a sleeping Katherine in the car.
In the bar, they find Jo whom has a bandage around her neck. Damon compels her to tell him what happened and she reveals about Stefan attacking her and then him burning before Qetsiyah threw him into a truck. She mentions how she knows who's truck it was and directs them to the hut.Before though she offers Damon a drink and he accepts until he realizes it is filled with vervain. Nadia comes in telling them that she threatened Jo's life if she didn't do it. After a violent confrontation with Nadia, Elena decides to save Katherine from Nadia while Damon goes to find Stefan. Before parting ways Damon tells Elena not to risk her life in saving Katherine as she is not even worth a hair on Elena's head and then they kiss.
Damon finally reaches the hut and finds Stefan tied up in veins on a chair. He tries to free him but can't. Stefan mentions how Qetsiyah is back. Qetsiyah reappears and tells them that she is going to create a link between Stefan and Silas so that she can disable Silas' mental powers. Despite Damon's reservations, Stefan agrees to it.She does the spell in which she begins to fry Silas' brain. Stefan falls unconscious. Damon tries to wake him but it doesn't work. Qetsiyah reveals that he will wake up in time and then mentions to Damon how his relationship with Elena is doomed. She reveals how every incarnation of the doppelgängers, always meets and falls in love and conquers all, saying it is the doing of the universe. She mentions to Damon, that he can leave Stefan with her so that he can continue his relationship with Elena with no interference. But Damon decides to kill Qetsiyah, but she is able to knock him out. Qetsiyah leaves and Elena arrives and goes strait to Stefan not even noticing Damon. Damon is clearly hurt by this.
Back at the Salvatore house, Stefan is still unconscious while Elena appreciates Damon for being a good brother but he doesn't say anything. Elena asks what Qetsiyah said to him back at the cabin. Damon tells her about how she explained that the universe is working against them to bring Stefan and Elena together and so they don't stand a chance. Elena responds by saying that Qetsiyah is crazy and she won't let Silas' 2,000-year-old ex-girlfriend screw things up between them. Damon emotionally tells her how he won't let a stupid idea of destiny stop him from loving Elena or being with her or building a future with her because she is his life. Elena, touched deeply by his words, leans in to kiss him but they are interrupted by Stefan who wakes up and tell them he has no idea who Elena and Damon are.
In For Whom the Bell Tolls, Damon is helping Stefan remember his past.While enjoying a ride together Stefan assumes that Damon is the safe brother while Stefan is the fun one which amuses Damon. Then Damon flips the car and Stefan realizes Damon is actually the fun one. The next day in the grill, Elena visits them and she and Damon discusses about how to deal with Stefan. At the Salvatore mausoleum, Damon is honoring their dead family members by ringing the bell when he gets a text from Jeremy for meeting him alone and so Damon leaves.
Back at the house Jeremy is trying to tell Damon about Bonnie's death. He starts of by telling him that no one can be brought back from the dead without consequences and Damon starts to realize what he is hinting at. Damon begs Jeremy not to say it but Jeremy finally confesses that Bonnie is dead. Damon is furious and starts to walk towards Jeremy angrily looking like he is about to hit him but instead he hugs him.
Elena calls Damon to help him find Stefan while he is trying to tell her about Bonnie's death. They finally find Stefan back at the house but he is still upset with them as they didn't tell him about them being together and leaves the house. Elena tells Damon that they need Bonnie to fix Stefan's memory and Damon finally tells her about Bonnie's death which shocks her. Later, Elena is freaking out as she can't find a dress for Bonnie's funeral and breaks down into tears telling Damon how she can't do this again. Damon hugs her affectionately and tries to calm her down. At Bonnie's funeral Damon consoles Elena as they both mourn Bonnie's death.
In Monster's Ball, Damon showed at Elena's school as she has been avoiding him to accept her invitation to the Whitmore Historical Ball. It's the one time of year that the college's entire collection of artifacts is put on display and people dress up as historical figures. Back in Mystic Falls, Damon told Jeremy that he wants to work with Silas. Since Silas wants to die to reunite with his own true love, why not use his death to reunite Bonnie with Elena. Nature loves a balance. When Silas takes the cure and becomes a witch, he might be able to do a spell that swaps his life for Bonnie's. Silas can't be trusted, and there are consequences when you abuse magic (especially when you're resurrecting someone). She said not to do this, but Jeremy told Damon that she was in.
During Damon's conversation with Silas, we learned that Silas saw Qetsiyah buying a Cleopatra costume, so she'd be at the costume ball as well. And Silas needed Damon to kill Stefan. At the costume ball, Elena and Damon were dressed as Anne Boleyn and and Henry VIII. Damon wanted to dance but Elena wasn't in the mood. She said it's not her fault that Bonnie died but it is her fault that she didn't figure it out sooner. She's not gonna let Megan's death fall through the cracks, too. Qetsiyah approached Stefan at the bar and wanted to buy him an "I'm sorry" drink. It would take a keg, Damon said, and led Stefan away. Stefan critiqued Damon as a wing man -- "Trust me, the last guy to hit on her is still paying for it," Damon responded -- and then Silas was there. "Hello, me." Damon snapped Stefan's neck. When Stefan is "dead," the link between them is gone and Silas has his psychic powers back. Silas was going to pose as Stefan.
Later, Stefan came to. He was pumped with vervain, so Damon could easily snap his neck again after he explained he was doing this to get Bonnie back for Elena. When Silas had a headache again, Stefan tricked Damon and snapped his neck. "How's it feel, brother?" Damon and Elena found Silas. Elena thought it was good that Silas is out of commission. But Damon knew it wasn't. Because they needed him to get Bonnie back.
Back at Salvatore Mansion, a desiccated Silas was on the couch as Elena and Damon talked. The only way for Silas to trade his life for Bonnie's is if he's a witch. The only way to become a witch is to have the cure. Someone was knocking on the door and it turned out to be Katherine. Katherine thought she was there so they could show her that she'd eluded death yet again. They finally did something right for once. How did it feel? "Thrilling," Damon said. And she figured it out. Damon bit her neck and she begged him: She said Silas would need all of her blood and she didn't want to die. "Goodbye, Katherine," he said, and he held her head down to Silas' mouth. Silas' hand came up to her head. Katherine dropped to the floor. But then Damon heard something. Her heartbeat. She awoke. "Am I in hell?" she asked.
In Handle with Care, when Damon and Elena are snuggling on the couch and having a sweet moment, Silas comes in ruins their blissful moment to discuss their plans for his death. Elena is having trouble trusting Silas' word that he will bring Bonnie back before he departs the mortal world for good, so he snarkily offers to pinky swear. Everyone is looking for the anchor now. Silas wants to die and find peace. Silas then refuses to allow Elena to come along when she looks like his true love and doesn't want to stare at her all day. As Elena gets annoyed, Silas uses his magic to shoot the crossbow at Elena's leg. This upsets Damon and he hurries to help her.
Damon, Silas, and Jeremy take a road trip to New Jersey only to end up at a huge warehouse full of junk that holds the anchor, so they begin the search for the anchor. When Tessa lures Elena to the cabin in order to use her as leverage against Damon. She wants Damon to kill Silas before the sun sets, or she will kill Elena. Damon tells Jeremy that the deal is off and Bonnie isn't returning because he has to kill Silas to save Elena. Damon walks back into the warehouse and is greeted by a Traveler speaking a foreign language, and is soon ganged up on. They manage to neutralize his daylight ring (reminiscent of the witches in Mystic Falls), and say that they don't want Silas dead yet...right before Damon kills them both. At the warehouse, Amara is stumbling around murmuring to herself, “leave me alone.” Damon finds her.Damon and Jeremy are throwing a pity party for themselves due to their failure to bring Bonnie back. They let Elena in on the big twist for the episode though, and Damon introduces Elena to Amara.
In Death and the Maiden, after Silas is no longer interested to bring Bonnie back, Damon turns to Qetsiyah for help.He asks Qetsiyah to perform a spell which can make Bonnie the new anchor to the other side.She agrees to help them since with that switch, Amara will die and the Other Side will remain existent so she can be there with Silas for the rest of time. To perform the spell she needs blood from all three doppelgängers, Elena, Katherine and Amara to which Damon sarcastically replies "You want Doppelgänger blood? I've got Doppelgängers coming out of my ears."
During the spell, Silas intervenes and tries to stop it. The power goes out and in the chaos, Stefan who just wants revenge against Silas after what he has done to him kidnaps Amara while Silas and Qetsiyah start fighting. Damon comes in and catches up with Elena on where is Amara gone and she tells him to go find Stefan because he wasn't thinking right. Silas might have put him in that safe but they were the ones who were supposed to get him out of it. Damon reaches the scene and finds Amara dying. He does everything he can to keep her alive for a few more minutes so that Qetsiyah is able to complete the spell. They are finally successful as Qetsiyah completes the spell in time and Bonnie becomes the new anchor. At the end of the episode, Stefan admits to Damon and Elena that he wanted it to be them who would find him and get him out of that safe.
In Dead Man on Campus, Elena calls Damon to invite him to her party and also suggests to invite Stefan. Then Damon tries to talk to Stefan, but he's freaking out, reliving his repeated drowning. Damon can tell something is wrong, but Stefan won't tell him.
Later, at Elena's request, Damon decides to get answers from Dr. Maxwell. In Maxfield's lab, Damon pokes through his lab samples. He explains to Maxfield that he's going to inject him with a disease and he'll heal him with his vampire blood if Maxfield talks.Damon thinks that it’s sick that Dr. Maxwell turns innocent kids into vampires just for an experiment. Damon gets another tube of some kind of virus, it’s “rabies” into Maxwell. Then Maxfield explains he was trying to create a new kind of vampire that doesn't feed on human blood but instead he feeds on vampire blood. Damon tells Elena about Jesse feeding on vampires, and she makes him promise not to kill Maxfield. In the lab, Damon slices his wrist to heal Maxfield of the various diseases he's injected him with, but Jesse storms in, wanting answers from Maxfield. He sees Damon's bleeding wrist and attacks him. Damon isn't worried, since he's a much older vampire than Jesse, but he soon finds out the usual strength-age rules don't apply. Jesse tackles him out a door and into the hallway.Jesse overpowers Damon and begins to feed on him when Elena finds them. With Jesse attached to his neck, Damon tells her Jesse's about to rip his head off. Elena grabs a shard of the broken door and stakes Jesse, killing him, just as Caroline runs up in time to see it. Elena feels awful, but Damon tells Caroline she had no choice and leaves to deal with Maxfield.
Back in the lab, Damon cleans up as Maxfield secretly works his way free from his restraints. Damon plans to compel the whole thing out of Maxfield's head. When he sees a bag of labeled blood in the fridge, the number jars his memory. Damon remembers his own number from trials 60 years ago. Maxfield realizes Damon was an Augustine vampire, too. Maxfield breaks free and Damon is unconcerned as he runs to the opposite side of the lab. But then Maxfield hits his "emergency procedures" button and atomized vervain fills the room, dropping Damon. Damon wakes up in a cell that is hauntingly familiar. His initials are scratched into the wall and memories of his time in captivity, being tortured, come rushing back.
In The Cell, Damon wakes up in a cell with Wes Maxfield injecting him with vervain. He tells Damon that because he killed their test subject last night (Jesse), Damon's going to take his place. Maxfield tells Damon that after training Jesse to crave vampire blood, he's ready to take his research to the next level. Later Wes captures Elena too in a cell next to Damon. She wakes up and Damon confesses he's been there before and tells her about Whitmore's torture, including cutting up pieces of them every day. He was there for about five years. He made a friend, Enzo, a soldier in Europe during WWII, who was also a vampire. Elena tells Damon that her dad worked with Whitmore and was an Augustine. She doesn't want to believe he'd be part of a place that would cut Damon's eyes out and breaks down. Damon confronts her and promises her that he'll get her out of there.
Damon continues to tell her about his past and also tells Elena that Enzo's friendship is what kept him alive and holding onto his humanity. But the craziest part is that he also reveals he never told anyone, including Stefan, what happened during his Augustine imprisonment, so Stefan won't know where to look for them if he even notices that they're both missing. Damon explains how he escaped. They let the vampires out once a year for the Augustine's New Year's Eve party to show them off. They were weak from vervain and captivity. Whitmore demonstrates vampire blood's healing powers, using Mrs. Fell as a volunteer. She drinks vampire blood to heal her hand after he cuts it. Enzo comes up with a plan, suggesting one of them drink both of their daily rations of blood for a year so that when they're let out next New Year's Eve, one of them will have the strength to fight. They play rock paper scissors and Damon wins. Elena wants to know what happened, but Damon is not forthcoming with the details, saying only that it wasn't pretty. Elena convinces him to tell her by saying that she loves him and doesn't care what he did to escape. Damon finally tells Elena his shameful secret: he left Enzo to die during his escape. After massacring the party on New Years Eve and knocking over a candle, he tried to break the cage to free Enzo but the bars were vervained and he couldn't get him out. Damon flipped his humanity switch so he would stop caring about Enzo, and left him to die in the ensuing fire. Elena was horrified that Damon left Enzo.
Aaron comes down to the cells in the basement with his gun. He accuses Elena of killing Megan and possibly of killing his parents. Damon stops him, and says it was him. Damon explains that with Enzo dead, he had to carry out his revenge plan himself. He planned to kill all the Whitmores in a generation, except one, then let him grow up and start a family, and then kill all of them except one, and so on. Elena is disgusted and asks when the last one was. A few months ago, Sarah in Charleston. It was a weekend trip. Elena realizes they were together then. Aaron shoots Damon leaving Elena upset. When Damon wakes up, he finds Elena's cell empty realizing that Wes has taken her.
In Fifty Shades of Grayson, Damon uses the last of his remaining strength to punch at the stone wall until a chunk falls out. He reaches through the grate for the bullet Aaron dropped when he came down. Damon puts the bullet in the lock and bashes at it with the rock, then kicks the door until it opens.
Damon visits Stefan and tells him they have to go get Elena, but he doesn't know where she is, so they need leverage. Damon and Stefan find Aaron Whitmore and Damon tells Aaron to call his uncle to get Elena back, or Wes gets to try to reattach Aaron's arms. Aaron calls Wes and he agrees to meet them in his classroom. The Salvatores arrive with Aaron at Wes's classroom and find Enzo waiting for them. Damon tries to skip over introductions, but Enzo is eager to tell him how he survived the fire that Damon left him to die in. He reveals that one of the scientist spared him. Damon is ready to get on with killing Aaron, but Aaron mentions some files Wes gave him that are in his dorm room. Enzo tells Damon to stay with him as Stefan goes with Wes.
Back in the classroom, Damon continues refusing to react to Enzo's guilt trips. Enzo mentions that Wes poisoned him and he has to return for the antidote. Damon suggests they work together to save both Enzo and Elena. Instead, Enzo tells him that Wes said he couldn't return until Damon was dead. Then Enzo throws him out the window. Enzo keeps trying to come after Damon, but Damon refuses to fight him. Enzo is too weak from the poison to really attack. Damon tries to get him to tell him where Elena is, but Enzo desiccates before he can talk. Enzo wakes up in a lab. Damon tells him he injected him with everything labeled antidote. Damon reaches inside Enzo's chest and tells him he had to flip off his humanity to leave him. Enzo tells Damon that he was the most important person in his life and he ruined him and that he is just a monster and always will be.
Later at the Salvatore house, Damon finds Elena reading through her dad's journal. She found a reference to Megan in her dad's journal. He cured her from a congenital heart defect, which is why Megan had a picture of Grayson Gilbert in her phone. Damon isn't surprised that Elena is able to find the one positive thing out of all the torture. He doesn't understand how Elena can keep looking past all the terrible things that he has done. She says she loves him and accepts him and because she chose him. Damon replies that now he is choosing and he chooses to let her go. Elena begs him not to run away because she has done horrible things too and that she won't judge him after finding out that he was tortured for 5 years. He shouts at her to stop defending him. Damon confesses that he can't change who he is but he refuses to change Elena and leaves. Elena is devastated and starts crying.
In 500 Years of Solitude, Damon is having a tough time dealing with his break up. Jeremy and Matt find a drunk and depressed Damon at the Grill. Both are shocked as to why Damon would dump Elena. Later in the Boarding house, Damon pours Matt and Jeremy shots for all the horrible things Katherine has done to them through the years. Elena,Caroline and Bonnie also arrive and join the toast game. Stefan comes downstairs to tell everyone they're being insensitive, but Damon warns him not to let the fact she's an Elena lookalike could the fact she's a manipulative psycho. Stefan mentions her seducing both him and Damon, turning them into vampires and starting a war with the town that got them killed. But he goes on to say that before that she was just a frightened girl shunned by her family, and she became a survivor, so that's what he'll drink to. Damon mocks Stefan for being so easy on her after one night of passion. Their moment is interrupted by Nadia who explains she has found a way to save her mother. Damon forbids anyone to help, which Nadia expected, which is why she buried Matt in the safe somewhere on the property, without his ring.
When Elena & Stefan volunteer to save Katherine in exchange for Matt, Damon decides to spend his time torturing Katherine by controlling her mind. Damon picks up a pillow to smother an unconscious Katherine. But Liz Forbes comes in and stops him. "Every awful thing I've done is linked to her. She taught me how to kill, how to enjoy it. She ruined me and I can't take any of that back," he says. "Look at how much control she still has over you, Damon. Prove her wrong," Liz says. Damon continues to toy with Katherine but is stopped by Nadia by snapping his neck. Damon wakes up on the floor but stays still and listens as Katherine tells Nadia that she's been selfish her whole life and just wants to do the right thing for once. She asks Nadia to let her go. Damon is surprised by Katherine's act of selflessness.
After Stefan says his goodbye to Katherine he and Damon talk about their eventful days. Damon understands why Stefan was being nice to Katherine. She helped pull Stefan out of a dark place. Stefan tells him to fix whatever is going on with him and Elena. Stefan tells Damon that she is the best thing that has ever happened to him and Damon doesn't deny it and confesses that he can't live without her but he doesn't think he's any better than Katherine and Elena will be better off without him. He's trying to be selfless. Stefan gives him a look and convinces him to get her back. Damon jokes that when he gets Elena back and the whole universe freaks out for keeping the doppelgängers apart, Stefan should remember he's the one who talked Damon out of doing the right thing for all mankind.
Later, everyone gathers in front of the fire, going through bourbon. Jeremy hears Alaric. "Where the hell have you been? I thought you bailed on us to go find peace or something," Jeremy says. Alaric replies "Do you honestly think I'd leave Damon in charge and never look back?" Jeremy translates to Damon that Alaric says you are a dick. Damon's face lightens up as he realized Rick is here too and they toast.
In The Devil Inside, Damon has buried Katherine's body and won’t tell Stefan where. Nadia is also there telling the Salvatore brothers she wants her mother's corpse. Damon tells her she’s out of luck. Nadia gets mad and tries to make Damon give it to her but he quickly tells her no. At the grill, Stefan is trying to talk Damon into giving Katherine’s body to Nadia. Stefan is also giving him a pep talk about Elena. Caroline shows up, Damon starts calling her out on her hate for him.
Enzo is waiting for Damon at the Salvatore mansion, with a huge body bag. Inside is Aaron - still alive. He did some research into Damon’s revenge plot and thought that he would want to finish it off. Damon is trying to mend his ways and get back with Elena, so when Aaron wakes up, Damon snaps Enzo's neck. “I didn’t see that one coming,” remarks Aaron. Damon rips off his vervain watch and compels Aaron to leave town immediately. Then he is off to the party. Elena makes it to the party and sees Damon and she falls into his arms, but Mia completes the ceremony, and in the comforting hug, Elena becomes Katherine for good. Damon makes an impassioned speech for them getting back together - that he knows he screwed up and gave himself too much credit for thinking he would change her and her not enough for thinking she couldn’t change him. Katherine is having none of that. “I’m glad that I make you a better person, but that is too much pressure. I can’t be the only thing you live for.” Damon is absolutely crushed when Katherine/Elena says goodbye.
Aaron is on his way out of town, just as Damon compelled him to do. He stops when he sees a man laying in the road, and gets out to help. The man sits up - it is Enzo. Damon appears behind Aaron and informs him that he is here because of Elena. “She thinks I am a monster. She’s right.” Then he brutally feasts on Aaron’s blood.
In Total Eclipse of the Heart, Damon is first seen in Salvatores living room, when he is sleeping on the couch. Stefan comes to him and asks about this mess he has done to the room and about Aaron's corpse in his car. Damon and Enzo are telling Stefan that they are going after whole Augustine institution, to get the full revenge on them. Stefan says to Damon that he is better than this, but Damon says that he is better like this.
Enzo and him have captured Diane, who works for the Augustine and compel her to talk all she knows about Wes Maxfield. When they get all the information from her they kill her and are trying to find Wes on their own. Damon then seeks out Bonnie and Jeremy, so Bonnie will find someone to do the locator spell or Enzo is going to kill Jeremy. While Jeremy says that Damon is not going to hurt him, because Elena would never forgive him, Damon proves him wrong and says that Elena has already given up on him and takes Jeremy hostage while Bonnie is trying to figure out how get some witch for locator spell to save Jeremy. When the witch seems to fail, he tells Enzo to give them more motivation when it is taking too long to find Wes. When Katherine and Stefan find Jeremy, Stefan and Enzo then fight each other. Damon then appears and tells Enzo he found Wes' location as Damon is about to walk away, Stefan tells Damon "Don't bother coming back" and Damon replies "I wasn't planning on it."
Damon leaves with Enzo to kill Wes, with Stefan looking upset about Damon's bad choice to leave with Enzo. But they then walk straight into a trap and are ambushed by travelers who are attacking them. While the Travellers are holding Damon and Enzo down, Wes infects Damon, turning him into an Augustine Vampire. Damon then tells Enzo that if what Wes injected him with what he thinks he did they're going to have a problem. At the end of the episode, Damon finds another test subject vampire who is bleeding and then begins to feel his body elevate at the smell and sight of his blood. Damon then violently feeds on the test subject to the point where Damon rips his head off. Damon then turns to a shocked Enzo seeing they have a problem then stares at Damon who stares menacingly back at him in shock of what has happened to him. The episode ends, with Damon looking at the camera with him covered in blood.
In No Exit, Enzo and Damon just got done killing a couple at a Farm house. Enzo is keeping tabs on Damon, tracking his eating habits. Enzo is making their victims into vampires so Damon can feed. The farmer tells them his wife left him for a pharmacist, then Damon kills him. The Travellers appear and trap the pair in the house. Wes is also there, he wants to run another test, trapping him in there with his only source of food, his best friend. Later, Damon and Enzo are still stuck in the farmhouse. Damon is getting antsy. Enzo tells him “calmer heads will always prevail”. He also tells them he should call one of the Mystic Falls gang for help. Damon tells him he won’t feed on him and he’ll find another way. Enzo ties him up. He tells Damon that Damon’s problem is that he runs. Enzo tells him that he’s calling for backup. Damon gets mad. Enzo calls Stefan’s phone and tells her what’s going on. Katherine tells him to text her the directions and they would be there soon. Wes shoots Enzo so Damon can smell his blood. Wes wants to know how strong and desperate Damon will get for blood. Damon starts feeding from Enzo whom is begging for him to stop. Damon starts choking. The Travellers did a spell to make Enzo's blood like acid. Wes tells Enzo he can come with them or stay with Damon. Damon tells him to go but Enzo is hesitant. He leaves with Wes.
Katherine shows up, Damon is begging her not to come in. Damon asks them to leave but Stefan tells him he’s not leaving. Stefan tells Damon he isn’t afraid of him when he goes to attack him. Katherine walks inside saying “neither am I” but then gets stuck in the house. Katherine even cuts her hand, Damon is trying so hard not to hurt her. Katherine keeps pushing him. Damon starts feeding from her and Stefan tries to get Damon to stop. Stefan picks up a piece of glass and cuts his arm. Damon goes to feed off Stefan then Stefan snaps his neck. Stefan is talking to Damon whom is strapped to a chair in the basement. Damon tells him one day he will kill him. Stefan tells Damon he isn’t going to give up on him and he never will. Damon brings up Elena, he knows that Elena has given up on him and that “she” wanted to kill him.
In Gone Girl, Stefan fills Damon in on Katherine is in Elena's body. "She's brilliant," is all Damon has to say. Stefan assures him to not to worry and that he has a plan. Later, Stefan feeds Damon 4 ounces of his blood, figuring that some every few hours will stave off his hunger. Stefan decides to call Katherine feeling that she won't say no to him like she has shrugged of everyone's attempt to meet her but Katherine instead calls Damon, wanting to talk. He invites her by the house. When she hangs up, Katherine assesses that Damon would never put Elena in harms way again after nearly killing her so he must have known that its Katherine. Stefan and Damon come to the same conclusion: Katherine knows that they know about her being inside Elena's body. Caroline and Stefan try to figure what to do next and then Damon suggests a locator spell.
Later, Tyler is guarding Damon and sits outside the cellar. Damon asks him what he's still doing in Mystic Falls with his whole family dead. He thinks Tyler is convinced there's still a chance with Caroline. Damon taunts him about Caroline until Tyler comes close enough and then Damon bites him and breaks free running to find Wes. Damon reaches Wes' lab and threatens him to make him a cure for the ripper virus but Wes refuses and Damon ends up killing him.
Damon reaches in time at the Salvatore house when everyone is planning to kill Katherine for good. Katherine taunts him by saying "But I never got to say what I needed to say to you. I’m sorry. You blame me for who you are, and I’m sorry. I’m sorry I turned you. I’m sorry I drove you to abandon the war. I'm sorry that you didn't get to die as a forgotten nobody on a bloody battlefield, that your father didn't get to live another day to be disgraced by you. Damon, I'm sorry that I gave your life passion, purpose, drive, desire. I'm sorry that you are who you are, because I'm the one who taught you how to love." Damon simply ignores her and adds ""I'll see you in hell, Katherine." Stefan then daggers Katherine with the Traveler's Blade killing her permanently.
Later, Damon along with Stefan is waiting for Elena to wake up. Damon tells Stefan that he plans on to tell Elena everything he did in her absence and is ready to face the consequences. He's determined not to be another Katherine and spend his whole life running. Elena then wakes up and Damon smiles at her. Elena greets Damon happily and assures him that its really her. It is then revealed that Katherine injected Elena's body with the enhanced Ripper Compound that Wes had made making Elena a vampire ripper just like Damon.
In While You Were Sleeping, Damon is being fed blood and watched by Jeremy and Matt. They taunt him about how Elena doesn't know Damon killed Aaron Whitmore but he warns them he will be the one to tell her. Elena is also locked in her dorm room because of the ripper virus and calls Damon after Stefan informs her of the ripper situation. They both are happy to hear each other. They are flirting when Elena asks him how Katherine broke his heart. He shrugs it off saying he doesn't remember. She then says "The last thing I remember I was running into your arms and I felt so safe," and he replies "It was all downhill from there." Elena then tells him how she wanted to fight for him and still want to, Damon joyfully replies "Oh Elena..the second we are cured of this and don't want to rip each other's heads off, I am going to hunt you down and give you the most mind-blowing night of your life." Elena excitedly says that she can schedule him in.
The werewolf venom insides Elena makes her hallucinate stuff which leaves her disturbed, she calls Damon again and ask him to distract her. He mischievously asks what is she wearing making Elena blush. He then tells her about Klaus and Caroline. Elena asks why they don't just hunt down Wes for the antidote and Damon confesses he killed him. Elena is upset saying that he was the only family that Aaron has. Elena's hallucinations start going worse and makes her believe she killed Aaron. Elena calls Damon in a panic, she can't tell what's real anymore. She tells Damon she thinks she killed Aaron. Damon promises to tell her everything, but says now isn't a good time. She freaks out, yelling that everyone is lying to her. Damon gets worried and manages to free himself from the cell while Elena threatens Liv to drop the seal and then goes out of the campus.
Damon finds a disturbed Elena and tries to help her. He gives her Stefan's blood to drink. "She won, Katherine won," Elena said. She rants about nearly killing Liv and killing Aaron Whitmore. Finally, Damon tells her she didn't kill Aaron but he did. Damon then reveals why he did, because the only person he believed could change him from being a cold blooded killer to a better person instead told him that he could never change. He waits for her to say something, but she sees Enzo there with the antidotes.
Back at the Salvatore Mansion, Damon offers Elena a drink to which she declines and then goes says how Damon should have noticed that it was Katherine not Elena. If he had, Aaron would still be alive, there'd be no virus. Damon points out she's blaming Katherine for his mistakes and making excuses for him. Damon says he killed Aaron because she broke his heart and this is how much control she has over him while Elena says that even after all this she is still here and this is how much control he has over her. He calls their relationship toxic and Elena confesses how she has to compromise her morals again to make excuses for him and she does it because she loves him. He tells her to stop loving him, but she yells that she can't. Damon replies that this is the problem and they mutually decide to end their relationship. However they both gaze at each other longingly and Damon then kisses Elena to which she reciprocates. They begin to make out and Elena rips his shirt. They are then in Damon's bed and end up having hot passionate break up sex.
In Rescue Me, Elena and Damon stay woken up for 3 hours without saying anything after their night together, post break up. Elena's phone buzzes to remind her to go to Jeremy's parent-teacher conference. She starts putting on her clothes while Damon greets her. Elena says they're still bad for each other and still broken up and last night was a mistake. "Maybe we should keep making mistakes," Damon replies. She leaves, despite his offer of a naked breakfast. Damon heads to the Grill to drown his morning sorrow in booze. He seeks relationship advice from Tyler and Matt and mentions that Caroline is off doing something with Stefan, although he taunts Tyler by assuring him they're just friends. Later he sees Bonnie's new witch friend Liv hanging with Jeremy.
Damon then visits Jeremy's school to attend his parent teacher conference and surprises Elena. Waiting for the teacher at school, Damon flirts with Elena, who tries to keep him on task. Damon mentions seeing Jeremy with Liv and a bottle of booze this morning at the Grill. Elena is sure Jeremy's not a cheater. Then the teacher comes in and complains about Jeremy saying "Jeremy's missed 11 days of school, he's started three fights and he's been caught cheating in math class twice." When the teacher realizes that Damon and Elena have broken up she tells them that Jeremy needs a stable living situation.
After talking with his teacher, Damon points out that Elena is making excuses for Jeremy, just like she always does with people she loves. She thinks he wants to talk about last night. He corners her near the locker and admits he doesn't know what to say, but just wants to take her into one of the classrooms and kiss every square inch of her body while people who drive minivans listen and wish they were them but then adds that it is probably a bad idea. Elena tries hard to breathe and with great difficulty whispers right. Damon leaves by saying see you in class while Elena is left completely shaken. Later in chemistry presentation, Damon wakes a lost Elena. Unknown to him she was daydreaming making out with him and frustrated with their sexual tension she leaves the class room. Damon then finds Elena with Liv who is about to kill her. Damon saves Elena and starts torturing Liv for information. Liv doesn't cooperate and he is about to kill her but Jeremy stops him. He convinces Damon and Elena that Liv will help them protect Elena from the travelers.
At the Salvatore house, Jeremy tells Elena and Damon that he has decided to live with Matt and Tyler leaving both of them upset. Later, Elena is packing her stuff and Damon asks her to not leave but she says that when they are together they do bad things for each other and she can't live with that. Damon offers to drive her to Whitmore but Elena confesses that if he does that then she won't be able to control herself around him and thus they are gonna end up back here. Damon then slowly walks up to Elena, then she believes he is going to kiss her. Instead Damon then shushes her and does the selfless/right thing, he takes his hands around her neck then slowly kisses her forehead and tells her Travel safe. Elena then seems shocked by Damon's act of selflessness as he walks away, she then seems upset that he finally let her go.
Damon was originally a very free-spirited young man, who was best friends with his younger brother Stefan Salvatore, both of whom were instantly smitten with the vampire Katherine Pierce. He had a positive relationship with Stefan and he held his position as elder brother in high regard, being the one to teach Stefan how to fight when they were younger. As a human, Damon also held a sense of duty as he enrolled in the confederacy, however their father saw him as very irresponsible and reckless, proving he was very much a free spirit who did things on a whim, taking no mind to what people thought.
Damon could be considered much the opposite to his brother in many regards. Whilst they both were respectful and polite, Damon had a dark side which came to play when he fell in love with Katherine, whilst initially terrified at the prospect, his love for Katherine and dependency for her affections made the choice easy and he willingly drank her blood and conspired with her to kill innocent humans, a trait which passed on to his vampire lifestyle. Damon was very naive as a human, he loved Katherine deeply and recklessly, regardless of the consequences and not caring that his father was ashamed of him. His carefree life fell apart when Stefan betrayed Damon by alluding to their father that Katherine was a vampire; information that resulted in Katherine being trapped and taken to a church to be burned, also doing whatever he could to get her back, even if it resulted in his death.
And you know what makes me able to drink my fill and leave someone breathing and not rip their head off like my brother; is that I can revel in it. I can make it fun.
After he became a vampire, he left Stefan's side, wanting no part in the life of the man who betrayed him. He selfishly kept the fact that Katherine was still alive from Stefan, jealous that his brother had also been turned by their shared lover. By the time he appears in season one, he's been away from Stefan for at least eighty years (including the meeting in 1912), and he immediately begins taunting his brother, as a colder, more calloused version of his human self.
Throughout season one, Damon acts arrogant and sarcastic, showing little to no regard for human life and using whatever people he can get his hands on as his personal playthings. He shows pity to neither Caroline Forbes nor Vicki Donovan, even going so far as to kill Stefan's football coach to "prove" that he has no humanity left. He is also portrayed as a very impulsive vampire, known for his self-destructive behavior and his devious, sadistic mind. Despite this, he stays focused on his only goal: getting Katherine out of the tomb. This shows his ability for planning and forethought, and certainly the patience to wait one hundred and forty-five years for the necessary comet to return.
After Katherine is discovered to have been alive the entire time, and his reason for doing the things he has been doing shattered, Damon becomes more dangerous because he drinks alcohol constantly, bonding with others at the bar. He destructively taunts Alaric Saltzman about being the one to kill his wife, Isobel Flemming, but is confused when he finds that Isobel is Elena's birth mother. He tempts his brother with human blood, though he knows exactly what Stefan used to be, and when Stefan goes off the deep end, Damon helps Elena detox him. He also genuinely thanks Bonnie Bennett for disabling the device that could kill him, surprising her with his sincerity.
Every time his brother is put in a situation that endangers his life, Damon protects him, but he's not afraid to cause Stefan non-lethal harm. Despite his anger with Stefan for his actions in the past, he hangs around, protecting him and working with him, sometimes destroying the good in his life. Their perplexing relationship seems to center around Elena, who anchors them to Mystic Falls.
Elena is the oddity of Damon's behavior, the anomaly that makes his personality far from psychopathic. In the beginning of the first season, Stefan is prepared to give up on his brother, believing him to be an irreparable monster, but Damon displays true feeling for Elena. Elena Gilbert is physically identical to Katherine, the woman who turned him into a vampire, making her not only a constant reminder of what happened to him and Stefan, but a temptation to let history repeat itself. When Katherine reveals that she never loved him (in the beginning of season two), Damon reacts by trying to get Elena to admit that she loves him, and when she tells him that she loves Stefan, he reacts impulsively, set off by both Katherine and Elena choosing his brother instead of him. He kills Elena's brother, spending many weeks afterwards trying to make it up to Elena, showing true regret for his actions. Their relationship began with taunting and cruelty, but she became what he clings to for humanity; he became her occasional protector, a guardian of sorts. His impulsive actions often drive her away but she refuses to let him die, and he does the same for her.
With Elena influencing him throughout the second and third seasons, Damon becomes slightly kinder, if only for the fact that he no longer mindlessly kills and torments humans without good reason, and he controls himself to be strong for Elena's sake. He proves that he is capable of love, nobility, loyalty, and selflessness, masking the most intense of his emotions to spare himself from seeming weak, but expressing just enough to draw in a very small circle of friends (which he later drives away). He continues to claim that his emotions can be turned off, but several older vampires reveal that this is a lie; after a certain amount of time, a vampire has to pretend they can't feel. The only time Damon had ever admitted his pain was when Elena told him that she would never kiss him back, to which he responded, “Now I'm hurt.”
About halfway through the third season, Damon believes that Elena is trying to turn him into Stefan by constantly telling him to be the 'better man.' Others continue to underestimate him and, to display that he doesn't care at all, he kills Alaric, with whom he'd developed a strong friendship. He also spends time trying to make it up to Alaric after his ring brings him back to life, treating him like a friend even though Alaric is extremely angry with him. He also snaps and feeds from Caroline's father, and, after a very violent fight with Caroline, he is confronted by Elena. He's even cruel to her, accusing her of trying to make him into something he's not. His inner turmoil continues when Katherine reappears, and he recklessly takes her offer of a 'road trip,' leaving Elena defenseless only because he is mad at her. When he returns, he displays genuine regret and, in one of his most tell-all, modest moments of the show, he tells her that he will never leave her again, showing his extreme love and devotion to Elena, and his regret for making another impulsive decision.
I just have to say it once; you just need to hear it. I love you, Elena... and it's because I love you that I can't be selfish with you. Why, you can't know this. I don't deserve you... but my brother does. God, I wish you didn't have to forget this... but you do..."
He compels her to forget that he said this (late in season two), because he believes it would be selfish to confuse Elena with his feelings. This is right after Stefan apologizes for making Damon turn in 1864, something that surprises Damon to the point of revelation: He realizes what he's been doing to his brother, all following one stupid mistake. In reality, what Damon said to Elena proves that she has been molding him into a better person, because before that moment, he never would've done something so selfless. Damon also admits to missing his human life before he drunkenly kills Jessica Cohen in the middle of the road; this secret is kept from everyone around him. He lets the girl go, but immediately chases her down and kills her anyway in an effort to prove that he doesn't really care. When his spirits are down, Damon solves his problems with alcohol (mostly bourbon), but he often uses violence and murder to console himself.
By his own testimony, Damon claims that the reason why he can control his vampiric urges is because he embraces what he is.
Damon is also very self-confident, given that he'll confront older, stronger vampires like: Lexi, Anna, Pearl, Elijah, Klaus, Rebekah, Kol, Katherine, Rose and Silas. Without hesitation, and without regard to manners, even when they themselves pose no signs of hostility towards him. He often taunts them, which results in him nearly being killed quite often as they are undeniably stronger than him; though of course, there were cases when he was able to best them on some occasions, as in the case of Kol and Silas. Further into season 4, Damon seems to have lost part of his authoritative and dominating personality, most likely because of Klaus, who is much stronger, older and more powerful than him.
Despite Elena's influence, it seems that he is a very vengeful person and it is routed in his core. After the torture he and Enzo experienced in the 1950's, he continued to carry out the revenge he swore to take even well into his and Elena's relationship. This also proves him to be very secretive, as he told nobody of his experiences, not even Stefan in the aftermath of the torture until it was revealed in the present.
When Damon fed on Joey in Total Eclipse of the Heart, he was shown to have no remorse or guilt over ripping the young vampire's head off.
In No Exit, Damon appears to have much increased strength when he feels the urge to feed on Vampire blood, he has all the abilities that a normal vampire would have except, enhanced to much more extreme levels making him much more powerful than vampires that are much older than him. For example Damon was able to break free from his chains in a matter of seconds when Enzo chained him up. Though this is something any-other vampire might not be able to do.
Damon is very handsome, standing 5'9" in height with a well built, toned physique. His physical appearance is that of around a 22-25 year old despite being over 170. Damon has a light complexion with olive undertones and has a strong bone structure with high cheeks bones and a solid jaw line. He possesses darkened brown, almost black hair which hangs just over his ears, usually styled in a casual disarray yet sometimes gelled for special occasions. With striking, intense blue eyes contrasting wonderfully against darkened lashes and eyebrows, a "bad boy" smile, he can be described as relatively athletic, tall, strong, sexy and seductive. He also considers himself the "eternal stud".
Damon's clothing style has remained somewhat similar throughout the series, usually favoring darker clothing; black shirts, t-shirts and boots underneath darkened jeans and black trousers, although on occasion has been seen wearing lighter colors. Damon is rarely seen without his leather jackets and his favorite clothing designer is "John Varvatos". On special events, such as dances, he wears smart attire such as tuxedo's and dress shoes.
As a vampire, he wears a large Lapis Lazuli daylight ring enchanted by Emily Bennett, as a means to walk around in the sunlight as a vampire. The ring has the Salvatore crest and an embedded "D".
In flashbacks, as a human in the 1860's era, Damon generally wore the same attire as his younger brother; Stefan, including dress shirts with suspenders, waistcoats, dress coats, hats, cravats and leather laced boots as his usual style. His color scheme as a human was much lighter, Damon was seen wearing a red waistcoat, yet still formal, showing the Salvatore family's wealth. His hair was slightly longer in style, with slight curls, showing a much more youthful appearance.
"The Salvatore's may fight like dogs, but in the end, they would die for each other. At least they know what family means."
—Rebekah to Klaus
Stefan is Damon's younger brother, when they were human they were very close, best friends up until the arrival of the beautiful Katherine Pierce. After Katherine's "death", Damon swore to make Stefan's life a misery, and succeeded in 1912 by making him loose control of himself, fifty years after their last meeting. In the 1940's, for the first time since their transition, Damon showed a rare selflessness by backing out of his plan to join Stefan in war, so that Stefan could try to control his urges, as Damon would've been a bad influence. Despite unknowing the truth of Damon's selfless act, Stefan still returned the favor to his brother in the 1970's, sending Lexi to help Damon turn on his humanity. These glimpses of the past, it is shown that whilst they may outwardly despite the other, deep down they truly care. Before season one, the brothers hadn't seen each other since the early 1990's, their relationship having taken a steep turn for the worse, as their relationship was described as "violent and bitter". Due to Katherine's influence they became enemies, yet have recently began repairing their strained relationship due to Elena Gilbert, ironically Katherine's descendant and doppelgänger. Through the seasons, both fell in love with Elena and whilst she was the factor bringing them together, she is also the biggest strain in the brother's complex relationship. In the season four finale, although Stefan was heartbroken at Elena's choice, he admitted that was happy for Damon. Through this, they have proven just how far their relationship has come from their violent past. Whilst their relationship will continue to be tested, through the highs and lows, it is clear that the two share a strong brotherly bond.
In Season 5 they appear to be getting along better as brothers and appear to show much more care and concern for one another, though their bond will be tested through time.
"I'm not gonna let someone else's idea of destiny stop me from loving you, or being with you, or building future with you. Because... you are my life."
—Damon to Elena
Elena Gilbert is Damon's new girlfriend and his best friend. As the series progressed, he fell in love with Elena. Damon is a 170 year old immortal who is described as seductive, handsome, hot, impulsive and charming. Elena first met Damon when he was in Mystic Falls looking for his object of obsession for over a century, Katherine Pierce. He then talked to Elena but afterwards, compelled her to forget their meeting. Elena then met Damon again at the Salvatore Boarding House when she went to look for Stefan. After a while, she started to view Damon as self-centered, violent, sociopathic and cruel, especially when she found out that he continuously abused and used her best friend, Caroline Forbes against her will. She was horrified to discover that Damon was also behind all of the murders and unusual "animal" attacks in Mystic Falls. Originally, Damon disliked Elena and was rather apathetic about whether Elena lived or died. Although, Damon was drawn to Elena, mostly due to the fact that Elena bears an uncanny resemblance to the object of his obsession for over a century, Katherine. Although Damon and Elena often bicker and don't get along, Elena began to slowly warm up to him as she got to know him, befriending him in the process. But she still kept her distance due to Damon's constant immoral and impulsive behavior. Damon and Elena's friendship deepens with time and the two become closer, with Damon haven fallen for Elena and Elena developing feelings for Damon. Damon has repeatedly admitted that he is in love with Elena, however, Elena has admitted that she loves him too. Damon once told Elena that he loved her, but that he didn't deserve her, but Stefan does. He then compelled her to forget his confession afterwards. As opposed to Stefan, Damon is seen to be extremely selfish when it comes to Elena, willing to put the life of Elena's before anyone else's, including Elena's loved ones. It has been a consistency throughout the series that even though Elena cares deeply about Damon and has feelings for him, she still strongly loves Stefan and has repeatedly chosen him over Damon much to Damon's disappointment. But Elena and Damon are still closer than ever, and the sexual tension between them has even increased as Elena's emotions were heightened. During Season 4, Stefan ends his relationship with Elena because of her no longer fighting the feelings she has for Damon. Elena admitted to Damon that he was the reason of her breakup with Stefan and with Jeremy trying to kill her, Elena had to move with Damon. Stefan moves out when she moves in because of the relationship between her and Damon. Damon and Elena also had sex for the first time and became a real couple the night she moves in with him. Despite being sired to him, her feelings for him are real and she loves him either way. She will not be giving up on him. He may be selfish with his feelings but he doesn't regret it – when push comes to shove, he'll always put her first and it's for that same reason that he's always saving her when she needs him. Damon brings out a side of Elena that none of her past loves have been able to and challenges her in a way that no one else can. He hasn't taken advantage of Elena when he's had the opportunity. He's usually played fair with her, and he's always saying that she's the one woman he has to do the right thing by. When Damon and Elena are in the same room together, the sexual tension between them crackles and pops like a sparkler. And even when they aren't saying anything, the pair can carry on entire conversations through eye contact and body language. Damon loves her unconditionally without expecting anything in return because that's who he is. He loves her either way, human or vampire.
Alaric was Damon's best friend. It started out antagonistic towards each other since Alaric knew that it had been Damon who had killed his wife but it later turned out that she wasn't dead and that she had in fact been turned into a vampire by Damon. From that point on, they have been shown as becoming closer and they often team up to fight the usual threats to the town. Alaric is the only one (other than Elena) to call Damon a friend. They are seen often drinking together; it's often seen that they do taunt each other as well though. Throughout the series, they become like brothers. Towards the end of Season 3, Alaric was turned into an Original Vampire by Esther and fed on Bonnie to complete his transition and then took the White Oak Stake from Bonnie. Alaric died in Damon's arms in season 3 finale, moments after Elena's death causing Damon to break down having lost his first real best friend since him and Stefan became vampires. But when Alaric appears as a ghost we learn that he will always be watching over Damon.
Jeremy is Damon's new roommate and , Elena's, younger adoptive brother/biological cousin. Their relationship is similar to the relationship Damon has with Alaric. It's complicated between them but Damon is a father figure to Jeremy. Even though Damon goes about things the wrong way, Jeremy knows he means well and has good intentions in helping people and trying to do the right thing. There are times when Damon has treated Jeremy like a little brother and is a mentor to him. After Alaric's death, Damon trains Jeremy in how to fight and kill vampires. There are even times when they protect each other. Damon does his best to keep Jeremy alive for Elena's sake as he is the only family she has left and multiple times when Damon has told Jeremy to kill him but he refuses to do so, proving they do care about each other. Currently, they have reverted back to enemies due to Damon's uncaring persona and that he held him hostage and had a hand in his near-death.
"Enzo's friendship kept me alive, he gave me a reason to hang onto my humanity."
—Damon to Elena
Enzo is Damon's best friend. They were cellmates in 1953 where both of them were captured and used to be tortured by the Augustine society for scientific purposes. They both became close as they spend more time together. Enzo got an idea to free them from Augustine, however on the night when they executed their plan, Damon accidentally started a fire and was unable to free him. Damon then decided to turn off his humanity to escape the pain of leaving Enzo behind. They both meet again in 2011 and rekindle their friendship.
Damon comes home from the Confederate Army where he served with "General Groom's boys". He drinks and gambles as a human. Damon is often criticized by his father, or by his father to Stefan. Even though he is the second one to see Katherine, he is the first of the brothers to be with her. He wants to die rather than become a vampire but Stefan brings back the barmaid, Alice, for him to feed on. When they first turn, Damon is weaker than Stefan because he refuses to feed often. Damon often points out to Stefan that the blood is a weakness to him because it consumes him and makes him a killer, because he can't control his urges. Damon is better at compulsion than Stefan and it is assumed that Katherine taught him how to compel people. He kills Callie Gallagher, the daughter of a vampire hunter who captured Damon and used him as a circus act, when trying to kill Stefan.
As with the series, he initially serves as the main antagonist until the third book, where he becomes an anti-hero. In the books, he is born in Florence, Italy and is described as arrogant, charming and seductive, but he is known to keep his word. Ian Somerhalder's television portrayal is faithful to the handsome, hedonist of L. J. Smith's creation. Damon loves the undead life and all that it entails, and no one's ever quite sure if they should love him or hate him. He leaves countless broken hearts in his wake, but the heart Damon desires the most is Elena's.
Damon is a masculine name the Greek origin, from the Greek δαμαω (damao) meaning "to tame" or "subdue".
Damon's birthday is June 28 and is a Cancer.
He was the first vampire in the show to have killed someone.
Damon is extremely fond of dancing.
Damon occasionally smokes cigars.
Damon has a closet full of black leather jackets.
Damon's favorite bad word is "dick".
Damon doesn't like Taylor Swift but is willing to listen to her to impress girls.
Damon likes pickles.
Damon's favorite alcoholic beverage is Bourbon.
Damon's favorite clothing brand is John Varvatos.
Damon's favorite book is "Call of the Wild" by Jack London.
Damon read a bit of one of the Twilight books at Caroline's and hated it, while reminiscing Anne Rice's vampire novels. Also, he said Edward is whipped.
Damon is a descendant of Silas' Salvatore line.
Damon has read "Gone With The Wind," a classic romantic novel.
Damon mentioned that he attended college at one point.
The first powers Damon was seen using are no longer on the TV show because they were considered too supernatural. They were controlling fog, flight, and using a crow to spy on people. The crow died in the same episode as Zach, early on in season one.
Damon is starting to revert to his old devious ways of season two.
In the books, Damon is constantly shown as a very strong and powerful vampire. He has many powers and it is always noted that he really is an exceptionally powerful vampire. In the show, he is as strong as an average vampire of his age, but he is not compared to others like in the books. All of his unique powers are rarely shown in the show, nor is how he is naturally powerful compared to others.
In the books, Damon is considered by others as very dangerous, sadistic, and cruel. In the series, Damon is manipulative and cruel, but changes to help Elena in the search for information about Katherine and protects her from being taken by Klaus; he helps protect Elena from constant hazards and makes a promise that will keep them safe and away from the tomb; Caroline as Damon gives his blood to her to prevent her death.
Damon, at one point, had sexual relationships with four recurring characters:
Isobel Saltzman had an affair with him before and possibly after he turned her into a vampire.
Rose slept with him after they both got drunk, and developed true feelings for her.
Katherine Pierce had a sexual relationship with him in 1864. After her return, they nearly had sex but were interrupted when Katherine declared she never loved him.
In the books Damon owns a black Ferrari, and in the series, a blue Camaro convertible.
Damon shows friendship and loyalty to Elena, Stefan, Alaric, and Jeremy.
Damon and Stefan are roughly 350 years younger than their novel counterparts.
Damon was the second vampire to be bitten by a werewolf after Rose and before Katherine, and the second to be cured, after Katherine.
Damon is comforted by Elena in his "final moments" similar to how Damon comforts Rose in hers, both because of werewolf bites.
In the books, Damon has the ability to shapeshift into a crow and wolf. In the series, Damon can control a crow and the mist but they were removed from the plot early on.
Damon in the books loves being a vampire and he tried to return to that state when he was accidentally turned into a human; Damon in the series seems to love his hedonist life style as a vampire but, as he said to Jessica, he misses being human beyond anything else.
Damon has kissed a Petrova Doppelgänger in three season finales. He kissed Katherine in the first season finale, and Elena in the second and fourth seasons finales.
Damon is the fourth character who kills Elijah, following Alaric, Elena, and Klaus.
Damon has become friends with every character he failed to kill except Klaus.
Damon's exact age has never been stated in the series but he tells Alaric he is in his 160s, making his age between 162 and 169.
Damon usually wears black.
Damon, Stefan and Elena are the only characters who have appeared in all episodes.
He is connected by blood with both Petrova Doppelgängers: Elena and Katherine. He was turned into a vampire by Katherine's blood and Elena was turned into a vampire with Damon's blood.
Damon often makes references to the characteristics of other characters by nicknames.
Damon has turned three regulars into vampires with his blood, Vicki, Caroline and Elena. He also turned Isobel and Abby. This makes him the most used vampire in the show to be seen turning people into vampires, and all female.
Out of the three regulars that he turned, Vicki, Caroline and Elena respectively, he killed only Vicki. Caroline was suffocated by Katherine and Elena drowned, because of Rebekah.
He's the only known vampire that had other vampires sired to him.
Damon (to Elena) : "You must be Elena. I'm Damon, Stefan's brother."
Damon (to Elena) : "Living room, parlor, Sotheby's auction. It's a little kitschy for my taste. I see why my brother's so smitten. It's about time. For a while there, I never thought he'd get over the last one. Nearly destroyed him."
Damon (to Elena) : "Yeah. Katherine, his girlfriend? Oh, you two haven't had the awkward exes conversation yet."
Damon (to Elena) : "Oops. Well, I'm sure it'll come up now. Or maybe he didn't want to tell you because he didn't want you to think he was on the rebound. We all know how those relationships end."
Damon (to Elena) : "I'm a fatalist."
Damon (to Stefan) : "Great gal. Whoo. She's got spunk. You, on the other hand, look pooped."
Damon (to Stefan) : "Were you worried, Stefan? Scared we may be doomed to repeat the past? Isn't that why you play your little game, "I'm a high school human"?"
Damon (to Stefan) : "That's for me to know and for you to. . .dot dot dot."
Damon (to Caroline) : "This could have gone a completely different way."
Damon (to Stefan) : "How were tryouts? Did you make the team? Very Emerson, the way you reveal your soul with so many... Adjectives."
Damon (to Stefan) : "I saw Elena today, BTW. That means "by the way." She was at cheer leading practice. She looked so perky in her little short shorts. Just... simmer down, I didn't even go near her. I've got my own cheerleader now. Ooh, that reminds me, I gotta run. I have a date. Sweaty palms. Wish me luck."
Damon (to Elena) : "I like you. You know how to laugh. And you make Stefan smile, which is something I haven't seen in a very long time."
Damon (to Elena) : "She was beautiful. A lot like you in that department. She was also very complicated and selfish and at times not very kind, but very sexy and seductive."
Damon (to Stefan) : "That's not a problem. Because I've been invited in, and I'll come back tomorrow night and the following night and I'll do with your little cheerleader whatever I want to do. Because that is what is normal to me."
Damon (to Elena) : "I get to you. You find yourself drawn to me. You think about me even when you don't want to think about me. I bet you even dreamed about me. And right now, You want to kiss me."
Damon (to Stefan) : " Nice trick with Elena. Let me guess, vervain in the necklace? I admit, I was a bit surprised. It's been a while since anyone could resist my compulsion."
Damon (to Stefan) : " Guess I could just seduce her the old-fashioned way. Or I could just eat her."
Damon (to Stefan) : " Bad dream? Do you know how easy it was to get into your head just now? You really need some human blood. It might even the playing field. Football reference. Too soon."
Damon (to Stefan) : "Well, the vervain keeps me out of her head. Maybe that's not my target. Believe it or not, Stefan, some girls don't need my persuasion. Some girls just can't resist my good looks, my style and my charm and my unflinching ability to listen to Taylor Swift."
Damon (to Stefan) : "This is John Varvatos, dude. Dick move."
Damon (to Caroline) : "What's so special about this Bella girl? Edward's so whipped."
Damon (to Caroline) : "Because I live in the real world, where vampires burn in the sun."
Damon (to Stefan) : "It's cool not growing old. I like being the eternal stud."
Damon (to Stefan) : "I admire your effort, Stefan. Pouring yourself a drink then spiking the bottle with vervain. I'm not some drunk sorority chick. You can't roofie me. But I can't help but feel a little used. I thought we were having a moment. I have to go to the party angry. Who knows what I'll do?"
Damon (to Elena) : "A woman, I guess. Doesn't it always come down to the love of a woman?"
Damon (to Stefan) : " I'm stronger than you think."
Damon (to Zach) : " I don't guess I could talk you into bringing me a rabbit or something? I'd settle for Stefan's diet at this point."
Damon (to Stefan) : "You won. You got the bad guy. Now nothing could come between you and Elena. Except the truth. The lies will catch up to you, Stefan. As long as you keep lying to yourself about what you are."
Damon (to Stefan): " I got the town off our back. It was for the greater good but I'm sorry. And to prove it, I'm not gonna feed on a human for at least a week. I'll adopt a Stefan diet, only nothing with feathers."
Damon (to Stefan) : "And I can go back to sulking and Elena-longing and forehead brooding. This is fun, I like this."
Damon (to Stefan) : "Yeah. I'm done. "That's just like you, Damon. Always have to have the last word." "
Damon (to Stefan) : "'I don't, Damon. I can't trust you to be a nice guy.You kill everybody,and you're so mean. You're so mean,and...You're really hard to imitate,and then I have to go to that lesser place."
Damon (to Stefan) : "I'm on edge.Crash diet,and I'm trying to keep a low profile."
Damon (to Stefan) : "I'm onto you. Reverse psychology. It's a little transparent, but I admire the effort."
Damon (to Stefan) : "I'm impressed Stefan. Fun with Booze and darts,sentimental with football,and now starry night. What do you want,Stefan?"
Damon (to Stefan) : "I could rip your heart out and not think twice about it."
Damon (to Stefan) : "I have a bigger surprise,Stefan. I'm gonna bring her back."
Damon (to Stefan) : "There's a tomb underneath the church.The spell sealed Katherine in that tomb,protecting her."
Damon (to Stefan) : "If that's what you wanna call it.She's been trapped in a mystical holding cell for the last century and a half, but you're an expert on starving a vampire,so how do you think she's doing, Stefan? Did you know that witches can use celestial events to draw energy into their magic? Me either.But in order to give the crystal its power, Emily used the comet that was passing overhead,and in order for that crystal to work again..."
Damon (to Stefan) : "Downside, Long time in between comets and a couple of hiccups along the way with the crystal but the comet passed,and I got the crystal. And then Caroline got the crystal, and now Bonnie has the crystal and here we are."
Damon (to Emily) : "I don't care about them.I just want Katherine."
Damon (to Stefan) : "Katherine never compelled me.I knew everything. Every step of the way. It was real for me. I'll leave now."
Damon (to Elena): "Oh you were so much more fun when you were asleep."
Damon (to Elena) : "Well, you're IN Georgia. Without your magical little necklace, I might add. I can very easily make you agreeable."
Damon (to Elena) : "A little place right outside of Atlanta. Oh, come on, Elena. You don't wanna go back right now. Do you? What's the rush? Time-out. Trust me. Your problems are still going to be there when you get home. Look. Step away from your life for 5 minutes. 5 minutes!"
Damon (to Elena) : "If I've never met him, I wouldn't know him. I mean, it's not like we all hang out together at the Vamp Bar & Grill."
Damon (to Bree) : "I rocked your world."
Damon (to Elena) : "Vampires can't procreate. But we love to try."
Damon (to Elena) : "Come on, what? You don't like pickles? What's wrong with you?"
Damon (to Elena) : " Dead? It's not such a bad word. As long as I keep a healthy diet of blood in my system, my body functions pretty normally."
Damon (to Elena) : "Sorry I can't unhinge my jaw like a snake to consume alcohol."
Damon (to Bree) : "And I believe you. My dear, sweet Bree. That's why I'm almost sorry."
Damon (to Elena) : "Well, you're not the worst company in the world, Elena. You should give yourself more credit!"
Damon (to Elena) : "You were there in the road, all damsel-in-distress-like. And, I knew it would piss off Stefan. And... you're not the worst company in the world, Elena."
Damon (to Stefan and Elena) : "Rise and shine, sleepyheads."
Damon (to Stefan and Elena) : "Oh, stop being smutty."
Damon (to Stefan and Elena) : "If I see something I haven't seen before, I'll throw a dollar at it."
Damon (to Stefan and Elena) : "So, in order to open the tomb, we need to find the journal to get the grimoire to undo the spells. First things first-since you are Elena Gilbert, you're on journal duty."
Damon (to Giuseppe) (Flashback) : "Well, I never asked for your respect."
Damon (to Giuseppe) (Flashback) : "You're being cryptic now, father. Why don't you just say the word?"
Damon (to Jenna) : "My father never approved of anyone I dated, which only made me want them more. Of course. What about you?"
Damon (to Elena) : "Well, yeah, I was deliberately trying to get to the sink."
Damon (to Elena) : "There was a time when I trusted him more than anyone."
Damon (to Elena) : "I just want her back. I'm sure you can understand that."
Damon (to Elena) : "Then you understand what I will do if anyone gets in my way."
Damon (to Jeremy) : "I'm a fast learner. Quick reflexes."
Damon (to Jeremy) : "Hot trumps weird, trust me."
Damon (to Stefan and Elena) : "This is an interesting turn of events."
Damon (to Stefan) : "So am I. For thinking for even a second that I could trust you."
Damon (to Stefan and Elena) : "Of course I was going to do it by myself, because the only one I can count on is me! You made sure of that many years ago, Stefan. But you...You had me fooled."
Damon (to Stefan) : "Give me the book, Stefan, or I'm snapping her neck. And you and I will have a vampire girlfriend."
Damon (to a girl he is feeding on) : "Oh, so much better than your friends. But shh. Don't tell them. They might get jealous"
Damon (to Stefan) : "You're worried about me. That's nice. Don't be. There's no need. I'm fine. Why wouldn't I be? I spent the last 145 years with one goal: get in that tomb. I succeeded. Granted, Katherine wasn't in there to be rescued, but why dwell? You know, it's so liberating not having a master plan, because I can do whatever the hell I want."
Damon (to Stefan) : "Relax. I haven't killed anyone in too long."
Damon (to Stefan) : "Nothing is important, not anymore."
Damon (to Stefan) : "Great chat. I have to go and exploit some women in the name of grief, which I'm sure you understand."TTFN", said the Tri-Delt. Heh. "
Damon (to Alaric) : "Behold the teacher. Don't you have some papers to grade?"
Damon (to Alaric) : "Well, most things in life are. Sober's depressing."
Damon (to Alaric) : "You say that like you know me."
Damon (to Liz) : "Have you ever been so bent on someone, just to have your heart ripped out by them?"
Damon (to Liz) : "Is this what you do when there's no, um..Vampires? Organize bachelor raffles?"
Damon (to Liz) : "You know, a room full of women clamoring to win a date with me. Sounds tasty."
Damon (to Elena) : "No reason why. Do you know that I am one of Mystic Falls' most eligible bachelors?"
Damon (to Elena) : "What can I do for you? I'm a barrel of favors today. It's my new found purpose -- how can I help people?"
Damon (to Stefan) : "Where'd our girlfriend go?"
Damon (to Stefan) : "Hey, are you coming? The Real Housewives of Mystic Falls await."
Damon (to Alaric) : "Oh, yeah. L.A., New York. Couple of years ago, I was in North Carolina. Near the Duke campus, actually. I think—I think Alaric went to school there. Didn't you, Ric? Yeah, 'cause I-- I know your wife did. I had a drink with her once. She was—she was a great girl. I ever tell you that? Cause she was Delicious.Mmm.."
Damon (to Alaric) : "She came to me. All pathetic, looking for vampires. There was something about her, something I liked. There was something special."
Damon (to Alaric) : "No, I slept with her because I liked her. I turned her because she begged me to. Yeah. But you knew that, too, didn't you? Hmm. I guess she wasn't happy at home, wasn't happy with life in general, wasn't happy with you."
Damon (to Alaric) : "Ah, this is a shame. We're kindred spirits, abandoned by the women we love. Unrequited love sucks."
Damon (to Alaric) : "Sounds like I got a lung. Which means I get to sit here and watch you die."
Damon (to Pearl) : "What, are you crazy? It was 1864. Wake up woman. The world has moved on."
Damon (to Pearl) : "You wouldn't even know where she was. You've been under the ground for the last century and a half"
Damon (to Pearl) : "I no longer have any desire to see Katherine ever again. And there’s no way in hell I’m gonna play the role of your little minion."
Damon (to Kelly) : "On the contrary, I’m very old."
Damon (to Kelly and Jenna) : "You'd be surprised. My primary reason for existence has abandoned me and after today's events, the remains of the shakey ground that I walk on are about to go kaboom. Let's get hammered."
Damon (to Stefan) : "I say we go to Pearl's, bust down the door, and annihilate the idiot that attacked us last night."
Damon (to Stefan and Elena) : "It was more like a helpful exchange of information. And it's not like I had a choice. She's scary. Besides, she's gonna help me get Katherine back."
Damon (to Elena) : "How long are you going to blame me for turning your birth mother into a vampire?"
Damon (to Stefan) : "I've got 2 liters of soccer mom in the fridge. No?"
Damon (to Stefan) : "All right. Give my regards to the squirrels."
Damon (to Pearl) : "Pearl! Open this door. I swear to God I'll bust through and rip your head off."
Damon (to Alaric) : "Let me recap, You tried to kill me. I defended myself. You died. Then according to my brother, your ring brought you back to life. Am I leaving anything out?"
Damon (to Alaric) : "Am I? Why don't you ask her for yourself? Coward."
Damon (to Alaric) : "Teacher by day, vampire hunter by night."
Damon (to Elena) : "Oh, I understand. I understand. He's the reason you live. His love lifts you up where you belong. I get it."
Damon (to Elena) : "I can't protect you, Elena. I don't know how many vampires there are in there. That's how long it takes you to get your head ripped off. I have to be able to get in and get out. I can't be distracted with your safety. Or this will end up a bloodbath that none of us walk away from including Stefan. I know. I get it. I understand."
Damon (to Elena) : "Are you insane?"
Damon (to Pearl) : "Your merry little band of vampires spent the day torturing my brother."
Damon (to Alaric) : "That was fun. Oh, don't look at me like that. I know you hate me. Guess what? Everyone hates me. But you can't deny it. We were bad ass."
Damon (to Stefan) : "Oh come on. Just drink already. Come on, this self-detox is not natural."
Damon (to Stefan) : "How long did it take you to wean yourself of it the last time you indulged?"
Damon (to Stefan) : "I don’t get it; you know, you don’t have to kill to survive. That’s what blood banks are for. I haven’t hunted in a human in...God way too long"
Damon (to Stefan) : "Well, what are those holier than thou reasons? You know, we never actually discussed this. You know, I'd- I'd love to hear this story."
Damon (to Stefan) : "You do? Well, then you should just carry on, making the rest of us vampires look bad."
Damon (to Elena) : "You ask I come. I’m easy like that."
Damon (to Elena) : "No Elena, I will not go to your bedroom with you."
Damon (to Elena) : "It is what it is Elena. The Stefan you know was “good behavior Stefan”, ‘reign it in Stefan”, “fight against his nature into an annoying excessive level Stefan” but if you think there isn't another part to this then you have not been paying attention."
Damon (to Elena) : "Well, he doesn't want to be me. That doesn't mean that deep down that he’s not."
Damon (to Stefan) : "Come on, don’t be a downer, it’s a party for the founding families! That would be us. That would be rude to skip it"
Damon (to Stefan) : "Oh I still do. I just love that they love me."
Damon (to Elena) : "Have I entered an alternate universe where Stefan is fun?"
Damon (to Liz) : "You know I love a woman in uniform but I have to side with this one. You look...you look smashing"
Damon (to Elena) : "Really? “Oh but sheriff, someone buried her. Who would do that?” I know I know! Me! I mean I could compel him but he’s wearing vervain"
Damon (to John) : "You know that I could rip your throat out before anyone would notice?"
Damon (to Stefan) : "You want to hear the bad news or the really bad news?"
Damon (to Alaric) : "Yeah, and that would be a big coincidence if he didn’t just came back from the death 5 minutes ago. Where the hell did you get that ring?"
Damon (to Stefan) : "We have a problem Stefan and when I say problem I mean global crisis."
Damon (to John) : "How lucky for us, we have John."
Damon (to John) : "John, whatever I can do to help keep this town safe; even if it means spending time with you"
Damon (to Anna) : "I suppose I should be grateful, you learned how to use the bell"
Damon (to Anna) : "You’re playing house with half of a tomb of really pissed off vampires. What do you think was going to happen?"
Damon (to Anna) : "Well, it’s a coincidence, ‘cause I don’t do forgiveness. Just run along. And if you’re going continue playing house with these little vampires pets, you might wanna stop robbing the blood bank dry because they’re onto it."
Damon (to Stefan) : "I don’t want to brag but I would definitely take responsibility for this new and improved you."
Damon (to Stefan) : "Fine, whatever man, drink up. Just remember, we're trying to keep a low profile. Why don't you just walk up to Sheriff Forbes and ask her to tap a vein?"
Damon (to Stefan) : "Who do you think you’re talking to? I know what it’s like. That Jekyll and Hyde feeling, that switch, sometimes it goes off and you snap. Right now is not a good time for me to be worried about you snapping."
Damon (to John) : "Go for it! I'll kill every last one of them. Then I'll sever your hand, pull your ring off, and I'll kill you too. Do you understand that?"
Damon (to Anna) : "Ah, nostalgia’s a bitch."
Damon (to Stefan) : "I was just filling Elena on your extra-curricular activities."
Damon (to Elena) : "He's just back to boring, straight-laced, off the junk. You've successfully cured him of anything that was interesting about his personality."
Damon (to Alaric) : "Did words completely escape you?"
Damon (to Alaric) : "I’m not going to kill her in a crowd restaurant"
Damon (to Alaric) : "You can turn it off, like a button you can press. I mean, Stefan's different. He wants the whole human experience. He wants to feel every episode of How I Met Your Mother, so he shuts his feelings out. The problem is, as a vampire, your instinct is not to feel. Isobel chose the easier road — no guilt, no shame, no regret. I mean, come on, if you could turn it off, wouldn't you?"
Damon (to Alaric) : "Of course I have Rick. It’s why I'm so fun to be around."
Damon (to Cherie) : "Oh Oh Cherie, you won again. I hope I’m wearing my good underwear"
Damon (to Isobel) : "Well you caused quite a stir, you blew into town. Saw everyone except for the man who made you. I'm a little hurt. "
Damon (to Isobel) : "Now that I have your attention, listen up. You do not come into my town; threaten the people I care about. Going after Elena? Bad move. You leave her alone or I will rip you to bits because I do believe in killing the messenger. You know why? Because it sends a message. Katherine wants something from me? You tell that little bitch to come get it herself."
Damon (to Elena) : "I’m not gonna give the device to Isobel so she could give it to John who is going to turn it to kill me. I like being a living dead person."
Damon (to Bonnie): "I don’t trust you, I tried to kill you."
Damon (to Stefan) : "Would you like one? Say it, whatever it is, purge, get it out."
Damon (to Stefan) : "Same here, Elena is a very good friend. Actually, she might qualify as my only… friend. Is that a problem?"
Damon (to Stefan) : "I don’t need any proof, that’s a DNA test for John, Elena and Maury Povich to deal with but I know how well you deal with these bombs so… Sleep tight."
Damon (to Stefan) : "Oh and when you do tell Elena and she needs a friend to talk to about anything, I’m here for her."
Damon (to Stefan) : "Why wouldn't I be here? Bonnie deactivated the Gilbert invention, Isobel is gone and it's Founder's Day! I'm here to eat cotton candy and steal your girl."
Damon (to Stefan) : "Oh, you started this Stefan with that whole "I'm insecure, leave Elena alone" speech. I'm enjoying that."
Damon (to Stefan) : "You have no sense of humor, Stefan."
Damon (to Stefan) : " 'Damon humor'… Hey look, I get it, I get it. I'm the better, hotter, superior choice and you're scared, now that Katherine is out of the picture, that I'm gonna turn all my attention to Elena. But don't worry, Elena is not Katherine."
Damon (to Elena) : "I like you better like this. The period look, it… didn't suit you."
Damon (to Elena) : "Actually Elena, it is a compliment of the highest order."
Damon (to Stefan) : "Good cop, bad cop, I like it."
Damon (to Stefan) : "Oh, there’s only one “do gooder” role available. My bad. I’m sorry"
Damon (to Jeremy) : "What I did to Vicki was wrong. I'm sorry for my part."
Damon (to Jeremy) : "Life sucks either way, Jeremy. But, at least if you’re a vampire, you don’t have to feel bad about it if you don’t want to."
Damon (to Katherine): "You know, I came to this town wanting to destroy it. Tonight, I found myself wanting to protect it. How does that happen? I'm not a hero, Elena. I don't do good. It's not in me."
Damon (to Katherine) : "Because she did it for you. Which means that somewhere along the way, you decided that I was worth saving. And I wanted to thank you for that."
Damon (to Elena) : "I know this is probably the last thing you want to do right now but we should talk about what happened tonight."
Damon (to Elena) : "Really? Earlier, on the porch, we were talking, all cathartic, feelings exposed. Come on, we kissed, Elena."
Damon (to Elena) : "If you want to forget what happened fine but I can't."
Damon: (to Stefan) : "Woman certainly knows how to make an entrance."
Damon: (to Stefan) : "Katherine wants you dead; there's zero you can do about it; you would be dead but you're not. So clearly she has other plans."
Damon (to Stefan) : "She's Katherine. She loves to play games and you're fooling yourself if you think you're going to find out what she's been up to before she wants you to know."
Damon (to Elena) : "Yes Bonnie, I would love to know why a non-vampire was tortured by the vampire torture device that you let John Gilbert use against us. Speaking of your guilt, how's Caroline?"
Damon (to Elena) : "Great Elena. Walking on the sunshine, thanks for asking."
Damon (to Elena) : "I kissed you; I thought you kissed me back. Doppelgänger hijinks ensued. How do you think I'm doing?"
Damon (to Elena) : "No, I don't get hurt, Elena."
Damon (to Elena) : "You're scared. You think Katherine is gonna send me off the deep end, don't you? I don't need her for that."
Damon (to Elena) : "You know, why - why is it such a surprise that I would kiss you?"
Damon (to Stefan) : "Brother, don't you worry, our bond is unbreakable."
Damon (to Katherine) : "Don't pout. It's not attractive on a woman your age."
Damon (to Katherine) : "I have a question. Answer it and it's back to fireworks and rockets red glare. Answer it right and I'll forget the last one hundred and forty five years that I've spent missing you. I'll forget how much I loved you, I'll forget everything and we can start over. This could be our defining moment because we have the time. That's the beauty of eternity. I just need the truth, just once."
Damon (to Elena) : "That's me, your trusty bodyguard. Calm in crisis."
Damon (to Elena) : "No, I'm not upset. Upset is an emotion specific to those who care."
Damon (to Elena) : "You're surprised that I thought you would kiss me back? You can't imagine that I believed that you would want to?"
Damon (to Elena) : "That what we've been doing here means something? You're the liar, Elena. There is something going on between the two of us and you know it."
Damon (to Jeremy) : "You want to shut out the pain? It’s the easiest thing in the world. The part of you that cares just goes away, all you have to do is flip the switch and snap!"
Damon (to Alaric) : "I've been on this planet one hundred and sixty some odd years, never came across one. If werewolves exist, where the hell are they?"
Damon (to Alaric) : "Rick, we need to know what we are dealing with. If this wolf men thing is true, I've seen enough movies to know it’s not good. It means Mason Lockwood is a real life Lon Chaney and that little Tyler punk may just very well be Lon Chaney junior which means Bella Lugosi, meaning me, is totally screwed."
Damon (to Elena) : "How are you doing back there? You know, this whole pretending to hate me thing is getting a little silly."
Damon (to Elena) : "Elena, I saw the ring! It’s a big tacky thing, it’s hard to miss"
Damon (to Elena) : "Pull it out. I can’t reach it Elena. Just pull the damn thing out. It hurts.That bitch is dead."
Damon (to Elena and Vanessa) : "I'd be extra nice to me right now."
Damon (to Elena and Vanessa) : "You know, if you want to see me naked, all you have to do is ask."
Damon (to Elena) : "Ah, man, you know, it’s a bummer we’re not friends anymore because I could tell you what I know."
Damon (to Elena) : "You’re not gonna be able to hate me forever."
Damon (to Elena) : "You have every right to hate me, I understand but you hated me before and we became friends. It would suck if that was gone forever. So, is it? Have I lost you forever?"
Damon (to Elena) : "I thought friends don’t manipulate friends. You and Katherine have a lot more in common than just your looks."
Damon (to Jeremy) : "And you’re a Gilbert and you just can’t help yourself. Wow. Your search for life's purpose is as obvious as it is tragic."
Damon (to Alaric and Jeremy) : "If we start believing in some supernatural witchy-woo legend from a picture book, we’re idiots. "
Damon (to Alaric and Jeremy) : "It's the same book that says a werewolf bite kills a vampire. Ignoring it would make me an even bigger idiot. Let's go."
Damon (to Stefan) : "That's the beauty of Katherine; she’s always up to something."
Damon (to Stefan) : "He (Jeremy) is playing Indiana Jones. He involved himself."
Damon (to Bonnie) : "How inconvenient. Although, let’s talk about that little witchy juju thing you do with me. You know, the fun one where my brain burst into flames? What is that?"
Damon (to Bonnie) : "Mason Lockwood’s a werewolf, Katherine’s evil. They’re the bad guys. Really? You’re gonna play morality police with me right now? Let me put it to you another way: they’re a threat to Elena. So you, witch, are gonna get over yourself and help us"
Damon (to Mason) : "You can hurt, good to know. I was afraid you were gonna be some beast mass with no affinity for pain.'"
Damon (to Mason) : "Now, now I get it. You’re just stupid. Katherine doesn't love you. She's using you, you moron."
Damon (to Mason) : "You know, I look at you I see myself. A less dashing, less intelligent version."
Damon (to Mason) : "Oh, I know! I've been where you are. But Katherine will only rip your heart out. Let me do it for her."
Damon (to Katherine) : "Aww, did I put a kink in your master plan? I’m so sorry."
Damon (to Stefan) : "Can we not do the whole road trip bonding thing? The cliche of it all makes me itch."
Damon (to Stefan) : "The elephant in the room lets out a mighty roar."
Damon (to Elena) : "Well, because what I’m about to say is… probably the most selfish thing I have ever said in my life."
Damon (to Elena) : "No, I just have to say it once. You just need to hear it. I love you, Elena and it’s because I love you that… I can’t be selfish with you. Why you can’t know this. I don’t deserve you but my brother does. God, I wish you didn't have to forget this but you do."
Damon (to Rose) : "You know, if you’re gonna be morn, I’m just gonna kill you myself just to put me out of your misery."
Damon (to Elena) : "Death happens. We come, we go. Sooner she dies the better. It’s gloomy as hell in here."
Damon (to Jules) : "You won’t live to see another full moon unless… unless you tell me how to cure a wolf bite and then I won’t kill you."
Damon (to Rose) : "I‘m not nice. I’m mean. I like it"
Damon (to Elena) : "What do you want to hear? That I cared about Rose? That I’m upset? Well I didn't and I’m not."
Damon (to Elena) : "I feel Elena, okay? And it sucks! What sucks even more is that it was supposed to be me. Jules was coming after me."
Damon (to Jessica) : "Hi Jessica. I have a secret, I have a big one and I never said it out loud. I mean, what’s the point? It’s not gonna change anything, it’s not gonna make me good, made me an adopt a puppy. I can’t be what other people want me to be, what she wants me to be. This is who I am, Jessica."
Damon (to Jessica) : "But I have to, Jessica because I’m not human and I miss it. I miss it more than anything in the world! That is my secret but there is only so much hurt a man can take."
Damon (to Stefan) : "You brought back John Gilbert? That was your big "Save Elena" move?"
Damon (to Stefan) : "We’re not that desperate, Stefan. The guy tried to barbecue me!"
Damon (to Stefan) : " I am still waiting for the part where John Gilbert is the answer."
Damon (to Stefan) : "Great work Stefan. Top notch. As if I didn't have enough problems."
Damon (to Stefan) : "It means I care, Stefan. It means I’m changing, evolving into a man capable of greatness. Better watch your back, because I may just have to go get a hero-hairdo of my own, and steal your thunder."
Damon (to Elena) : "I’m joking. Okay, I’m a little serious."
Damon (to Elena) : "I’m not gonna hurt him, Elena. I’m the good guy now, remember?"
Damon (to Elena) : "I’m gonna have a civil conversation with your father."
Damon (to Elena) : "Yeah, but stupid is so much more fun."
Damon (to John) : "It’s an acquired taste. I don’t see that magic little ring on your stitched finger, so if you know something about Klaus, you better start talking, or I will kill you in your sleep."
Damon (to Andie) : "My glass is all full, Andie. Thank you."
Damon (to Elena) : "I'm steering clear of all women at the moment."
Damon (to Elena) : "Trust me, it’s in the best interest of women everywhere."
Damon (to Elena) : "He’s a werewolf, he needs to die. I’m willing to kill him, it’s win-win."
Damon (to Elena) : "You need to stop doing that. Assuming that I’ll play the good guy because it's you who’s asking."
Damon (to John) : "First dad duty: ground your daughter. Keep her here."
Damon (to Jules) : "My brother the peacemaker. Since Stefan got here before me I’m gonna let him try it his way before I resort to my way, which is a little bloodier."
Damon (to Andie) : "I like a woman who knows what she wants."
Damon (to Andie) : "I’m not that tall. I need a distraction."
Damon (to Andie) : "You see, the thing is, Miss Sexy-Reporter-Girl, I have a problem I need help with. It’s really messing with my mind."
Damon (to Andie) : "I’m in love with a woman I can never have."
Damon (to Andie) : "Yeah. but that’s not the point. The point is, I’m in love with her, and that drives me crazy. I’m not in control."
Damon (to Andie) : "I don’t trust myself around anyone, Andie. I’m bad, Andie. I do things. I kill people."
Damon (to Andie) : "Because I like it. It’s in my nature, it’s who I am. But then, I have to stay together to protect her, and she wants me to be the better man, which means I can’t be who I am. Do you see the problem I’m having, Andie?"
Damon (to Andie) : "Just stop talking. Just kiss me, be my distraction."
Damon (to Alaric) : "My new girlfriend --Andie Star, action news."
Damon (to Alaric) : "I want to know his endgame before I kill him, but I do think it's time Elijah and I officially met."
Damon (to Elijah) : "You can't kill me, man. It's not part of the deal."
Damon (to Alaric) : "If I did, who would report her death?"
Damon (to Jules) : "Oh, if you only knew the irony of this moment right now. Let me tell you how this is gonna go. You're gonna torture me, I don't talk, someone loses a heart. Last time, it was your boy Mason."
Damon (to Jules) : "Get over it, honey. You're never gonna get it."
Damon (to Stefan) : "Something tells me he's not going to be 16 and pimply."
Damon (to Elena & Stefan) : "That was a lame, cheap shot. He's just trying to bait us."
Damon (to Elena & Stefan) : "It's a party, people. Blend. Let him come to us."
Damon (to Elena) : "Cool as a cucumber. Come on, remember the last decade dance? The vampires were all, "ahh!" And you were all, "aahh!""
Damon (to Elena) : "I've got moves you've never seen."
Damon (to Bonnie): "The part about you having a 50-50 shot of surviving? Is that true?"
Damon (to Elena) : "You need to listen to me, and prepare for what I'm about to say. Bonnie had to die. Klaus using Alaric's body was a total surprise. She wasn't prepared for that. And he wasn't going to stop, and we weren't going to be able to stop him until he knew she was dead. He had to believe it."
Damon (to Stefan) : "How do I know when you're going to go blabbing things to your girlfriend?"
Damon (to Stefan) : "See, that's why I didn't tell you. 'Cause you would have never been able to do it. Don't get me wrong, Stefan. I don't mind being the bad guy. I'll make all the life and death decisions while you're busy worrying about collateral damage. I'll even let her(Elena) hate me for it. But at the end of the day, I'll be the one to keep her alive."
Damon (to Elena) : "Let me be clear about something. If it comes down to you and the witch again, I will gladly let Bonnie die. I will always choose you."
Damon (to Katherine) : "You don't get a good-bye."
Damon (to Katherine) : "Us ending up on good terms isn't exactly on my bucket list, Katherine."
Damon (to Katherine) : "I helped you. You owed me. Now when Klaus dies, you're going to walk out of here without a scratch and Elena’s aunt dies. Somehow you're the only one that wins. How'd that happen?"
Damon (to Katherine) : "Enjoy an eternity alone, Katherine."
Damon (to John): "When Klaus kills Elena in the sacrifice, she will come back to life. Granted, as the thing you hate most in the world, but no one really cares what you think."
Damon (to John) : "You do not want to mess with me right now."
Damon (to John) : "I know, John. I took her choice, destroyed her future. Trust me, I get it. It actually gets worse."
Damon (to Alaric) : "We have a witch. She kills Klaus. No one has to die!"
Damon (to Alaric) : "I'm fine. Well, that's my brother for you. Always cleaning up my messes."
Damon (to John) : "Her soul, really? You're going to put your faith in some act of god mumbo jumbo?"
Damon (to Elena) : "If you come back as a vampire, I'll stake you myself. So don't. Because I can't stand the idea of you hating me forever."
Damon (to Stefan) : "I think I'll skip the coffee and tea cakes."
Damon (to Stefan) : "And then what's the plan, Stefan? The curse is broken. How does one go about killing an all-powerful wolf vamp and his two-faced older brother?"
Damon (to Stefan) : "You want to do something for me? Keep this from Elena. Last thing she needs is another grave to mourn."
Damon (to Elena) : "Yeah, you should learn to knock. What if I was...indecent?"
Damon (to Alaric) : "It's his signature; there's a reason they call him the ripper. Feeds so hard he blacks out and rips them apart, but then when he's done, he feels remorse. It's the damnedest thing, he put the bodies back together."
Damon (to Alaric) : "Covering their tracks. Clearly they have no interest staying in the dark, but I do."
Damon (to Alaric) : "I love high school parties."
Damon (to Stefan) : "Saw your latest artwork in Tennessee. Walking a fine line there my friend. Keep that up and there will be no saving you.'"
Damon (to Elena) : "No, you stop, Elena! Stop looking for him. Stop waiting for him to come home. Just stop! Stefan is gone and he's not coming back. Not in your lifetime."
Damon (to Elena) : "You're still wearing this necklace. Isn't this the reminder of your unbreakable bond with Stefan?"
Damon (to Alaric) : "I'm going to let you in on a little secret... Founders parties are just an excuse for the council to gather in back rooms and plot against vampires."
Damon (to Elena) : "Yeah, and when I kill him(Caroline's Dad), she'll have one more parent than we do."
Damon (to Bill) : "Makes you the third person to underestimate me today. Whoo. You know, with all this behavioral modification going on around here, I almost forgot how good blood tastes when it's...Fresh."
Damon (to Bill) : "No, I'm not going to kill you, Bill. I'm just going to find pleasure in perfect little moments like this."
Damon (to Caroline) : "Let me teach this ass-wheel a life lesson."
Damon (to Caroline) : "I'm stronger than you, little girl."
Damon (to Elena) : "Why not? It's nothing I haven't done before. Why is it suddenly so important for everyone to keep me in check?"
Damon (to Elena) : "What? A monster? Sorry to disappoint you, Elena, but last time I checked, I was still a vampire!"
Damon (to Elena) : ""I am not Stefan. How about you stop trying to turn me into him?"
Damon (to Alaric) : "Ric, no hard feelings, all right? I was on a bit of a tear. Everyone was trying to tell me how to behave."
Damon (to Elena) : "Elena! If this thing (grenade) blows up in our face- just remember: only one of us heals quickly."
Damon (to Elena) : "We thought of everything, Elena! Klaus having hybrids. Mikael turning on us. We brought in Katherine so you weren't in danger. Anything that could have gone wrong we were prepared!"
Damon (to Elena) : "She (Katherine) ran for the hills like usual, the minute things got bad! And who blames her?! Klaus would've crushed her. I had him, Elena. I had Klaus! This could have all been over!!!"
Damon (to Katherine) : "Not interested in the play by play of our failure right now, Katherine."
Damon (to Alaric) : "Oh, I give you a choice. Bloody Mary or Screw Driver. Brunch in a bottle. Come on Ric, I can´t drink all this by myself. I mean I can but then somebody's getting naked. Oh man I can't believe you're making me drink alone."
Damon (to Elena) : "You are feisty when you are mad."
Damon (to Klaus) : "You know me. Never miss a chance to plan an epic failure."
Damon (to Klaus) : "Such a buzz kill, my baby bro. Well, I´d love to find him. Just the trouble is, I sure as hell don't work for you."
Damon (to Stefan) : "I want you to get it through your head. Stop saving me!!"
Damon (to Jeremy) : "Here's the thing, Jer. You're gonna go out of town for a while- a long while. You're gonna stay with some nice family friends in Denver, you're gonna be at a new school, you'll meet new girls, living girls. You're going to drink a few beers, take an art class. You do whatever you want. You're gonna leave Mystic Falls behind and never think twice about it. You're gonna have a better life, Jeremy. "
Damon (to Elena) : "You just saved his (Jeremy) life, Elena. Take it from me, strange is bad, dead is worse."
Damon (to Elena) : "If I'm gonna feel guilty about something, I'm gonna feel guilty about this. (He kisses her)"
Damon (to Stefan) : "The only way to call someones bluff, Stefan, is to be willing to lose everything if you're wrong."
Damon (to Carol) : "Carol, don't take this the wrong way, but do you realize that you've been kissing the ass of an immortal hybrid who ruined your son's life?"
Damon (to Stefan) : "Don't give me that no-humanity crap, you can't just flip your switch! Your switch is fried, Stefan, just like your brain! You want to take Klaus? You want to beat the villain? You've got to be smarter."
Damon (to Klaus) : "Maybe he is, maybe he isn't but if you don't want to believe him, believe me. I know my brother better than anyone, and right now, I don't have a clue how far he is willing to take this. So if he says blink, I suggest you blink.!"
Damon (to Elena) : "It's right. Just not right now."