|“|| Elena: You lied to me...
Damon: Even if I wanted to apologize, you couldn't hear me. So I won't.
Elena: Please don't leave me...
Damon: I don't have a choice, baby. You are by far the greatest thing that has ever happened to me in my 173 years on this Earth. The fact that I get to die knowing that I was loved not just by anyone but by you, Elena Gilbert, is the epitome of a fulfilled life. It’s never gonna get any better than this...I peaked. I love you, Elena.
Elena: Please, please come back to me...
— Elena and Damon in Home
Damon came back to Mystic Falls with the sole purpose of bringing back Katherine Pierce, the vampire with whom he had fallen in love as a human in 1864. However, after realizing that Katherine had secretly escaped the tomb but hadn't cared enough about him to find him, he resented her. He begins to fall for his younger brother Stefan's girlfriend, also Katherine's doppelgänger, Elena. His love for Elena makes him want to protect his birthtown instead of destroying it, as was his original purpose when he arrived. They form a rocky friendship.
Elena constantly forgives Damon from doing horrible things to her, such as killing her younger brother Jeremy (although he came back to life) or feeding her vampire blood (essentially ending her human life). Elena has admitted she sees the good in Damon and believes he's worth saving. Elena begins to reciprocate Damon's feelings for her, though continues to love Stefan.
Their friendship deepens, leading to them becoming best friends. Elena cares whether Damon lives or dies, and even when she chooses Stefan over him, Damon continues to still be there for her when she needs somebody and feels she can't turn to Stefan about it. Damon has never lied to her and would always tell her the truth, although has admitted that he will lie to her if it saves her life.
After becoming a vampire, Elena breaks up with Stefan as her feelings for Damon had become too strong for her to ignore. Elena and Damon sleep together after she admits to her feelings. It's discovered that because Elena had feelings for Damon when she was human and it was his blood which turned her, a sire bond has been created between them. Damon begins to doubt her feelings for him and believes they are solely built on the sire bond. After being compelled by Rebekah to tell the truth, Elena reveals that she is no longer in love with Stefan and is instead in love with Damon. She later confesses this to him, stating that it's the most real thing she's ever felt. After Jeremy dies, Damon uses the sire bond to get Elena to turn her emotions off, knowing that the pain would be too much for her. She loses all feelings she has for him as a result, but continues a relationship with him solely for manipulation, later telling him her feelings were all due to the sire bond. Damon's willing to do anything to get her emotions back, including torturing her and killing Matt (although he was brought back to life), which eventually proved successful.
Elena later chooses between Damon and Stefan for the second time, this time choosing Damon, since she had fallen out of love with Stefan. She confirms her love for Damon during a heartfelt confession from them both, and they kiss. Damon's later proud as he says to Alaric, "I got the girl."
Their relationship lasts the whole summer and briefly becomes long distance when she begins attending college. After realizing how he's changing her, he decides to break up with her, causing her great heartbreak. Stefan makes Damon realize how he was stupid and he decides to try and win her back. However, when he finally tells her, he's unaware that Katherine has taken over Elena's body when she rejects him. This sends him off the deep end and he becomes guilty when he finds out the truth. After he tells her the truth, they mutually decide to end their relationship as they realize they have too much control over each other. However they end up sleeping together. But after that, Elena tells Damon that he has to let her go until they can figure things out.
As Markos, the Travellers' leader finally makes his appearance, Elena and Stefan begin to have visions of a life that they would never have. Damon is hurt by this but Elena lets him know that the universe doesn't control anything and that her and Damon are real, not those visions. She tries to be friends with him but he refuses and they try to avoid one another which turns out to be impossible. After getting kidnapped by Markos, nearly dying and with a little encouragement from Stefan she tells Damon that she thought she would never see him again and couldn't think of a worse way to die and so they both rekindle their relationship. In the finale of Season Five, in order to bring Stefan back from the Other Side, Damon and Elena go on a suicide mission. However, when the resurrection spell starts, Damon is unable to come back from the Other Side. Knowing that the Other Side is disintegrating and there is no other way for Damon to return, Elena breaks down completely. A ghost Damon confesses to her that she is the greatest thing that ever happened to him and the fact that he will die knowing he was loved by Elena Gilbert is the epitome of a fulfilled life. Damon says I love you and leaves while Elena continues to cry and pleas with him to return to her.
They are known as "Delena" by fans.
- "You want a love that consumes you. You want passion and adventure, and even a little danger...I want you to get everything you're looking for."
- —Damon to Elena
Damon first met Elena the night her parents died. She met Damon in the middle of the road, and at first, he mistook her for Katherine. They started talking and even flirted a little. He told her that she wanted a love that consumed her, a love that was passionate, and a love that was a little dangerous. And then he told her that he wanted her to have everything she wanted. After their moonlit conversation, Elena's parents had arrived and Damon compelled her to forget it ever happened. They were later reunited in The Night of the Comet, but she didn't remember him. This also explains the reason explains how Damon knew who Elena was when they met in the Salvatore Boarding House. Elena admitted in The Departed, that if she had met Damon first, she would have been with him instead. This memory resurfaces after Elena has transitioned into a vampire in Growing Pains.
Throughout the Vampire Diaries
In the Pilot, Damon spies on Elena by controlling a crow and a fog when she is writing in her diary at the cemetery.
Damon met Elena at the Salvatore Boarding House when she was looking for Stefan, his brother. He purposely told her about Katherine Pierce, an old flame of Stefan and himself, though he didn't mention her name. He wanted Elena to think Stefan was still heartbroken and on the rebound from the last girlfriend he had, which was Katherine. Elena left when Stefan arrived, sensing the tension between the siblings.
While hosting a dinner to get Stefan and Bonnie Bennett, who'd been suspicious of Stefan, to bond, Damon turned up along side Caroline Forbes, saying that they bought dessert.Stefan was against inviting Damon in the house, but Elena didn't mind as she didn't know that the Salvatore brothers were vampires. They talked afterwards, and the conversation eventually became about Katherine, with Elena realizing that Damon had loved Katherine as well by saying "I'm sorry, you lost her too."Damon felt uncomfortable talking about how he loved Katherine and quickly changed the subject to Elena quitting cheerleading.
Later that night after the hosting of the dinner get together, Elena dreams about making out with Stefan, who turns into Damon, frightening her. She was relieved that is was only just a dream, unaware that a crow was by her window, hinting that Damon may have been responsible. Later the next day as Elena was about to leave a rally, Damon showed up, saying that he was hiding from a talkative Caroline. He tried to use his compulsion on her and told her she was attracted to him, but before he could try and kiss her, she slapped him in the face, saying "I am not Katherine". Stefan, wanting to protect her from his brother, gave her a necklace containing a herb called vervain so that she wouldn't fall victim to any compulsion Damon tried to use or Stefan himself. Damon later went to Elena's house while she was sleeping and gently stroked her face, hinting at Damon's feelings and existing humanity, despite murdering Coach Tanner earlier in the episode.
At the Founder's Party, Damon apologizes to Elena and admits he's trying to punish Stefan by lashing out. Elena says she doesn't want to get in the middle of it but hopes that they are able to solve their misunderstandings. Later Elena realizes that Damon was hurting Caroline because of the marks that she found all over Caroline's body. Elena confronts him about it, which causes Damon to attempt to kill Caroline.
After Damon escaped from the Salvatore Boarding House basement, he came to Elena's house, looking for Stefan, who had taken his ring which could protect him from the sun, which if he didn't have that ring back before sun rise he would burn and eventually die. Damon immediately found out that Elena knew they were both vampires, because she tried to stop him from coming into the house. Before he leaves, he gives some advice to Elena, telling her, "Be careful who you let in the house."Elena was shocked that Damon had turned an already unstable Vicki Donovan into a vampire. At the Halloween Party, Elena found Vicki with Jeremy. When Vicki attacked Elena, Stefan staked and killed her in front of a horrified Jeremy. At home, Elena asked Stefan if he could use his compulsion to erase the horrible memories and the pain from Jeremy but Stefan didn't have the same amount of power (because he didn't feed on human blood), as Damon (who did feed on human blood), did to erase the memories. Damon volunteered to do it after he got rid of Vicki's body. On Stefan's birthday, Elena saw how happy Stefan was and saw how much fun he was having with his best friend Lexi, whom was also a vampire. Elena and Damon talked about it, Elena noted how happy Stefan was and that was something that Damon disliked.
Bonnie made several attempts to dispose of her necklace that had belonged to her ancestor Emily. Damon was trying to get the necklace because the crystal could help him retrieve Katherine from the vampire's tomb. Caroline, Bonnie and Elena held a séance to find out what Emily wanted, but Emily possessed Bonnie. Damon found out her location at the ruins of Fell's Church and tried to stop her from destroying the crystal but was unsuccessful. Elena was horrified when Damon, out of rage, attacked Bonnie, but was relieved when saved her, by feeding Bonnie his own blood.
Stefan decided to leave town and Damon decided to go with him. Plans changed when a new vampire started to attack the town of Mystic Falls; it was revealed to be Logan Fell who was killed by Damon as a human and was eventually killed by Alaric Saltzman. When Elena found a photo of Katherine, she left Stefan's and while driving on the road, her car ran into a hooded man, but he survived and made his way towards her overturned car. Frightened, Elena screamed, and once he saw Damon, he super sped away. Damon rushed to her side seconds later and pulled Elena from her car, rescuing her. She told him she looked like Katherine before passing out.
Damon took Elena to Georgia to see an old friend of his, a witch named Bree. Elena was shocked that Damon had taken her out of Mystic Falls, but she refused to talk to Stefan when he called. Damon took her to Bree's Bar and Elena decided that if she was to spend the day with him, she had to drink. The two ended up enjoying each other's company until Elena stepped out of the bar to speak on the phone and was kidnapped by Lee, Lexi's boyfriend. Lee wanted revenge for Damon killing Lexi but Elena made him remember that Lexi wouldn't have wanted him to do what he was doing. Elena saved Damon's life and he took her back to Mystic Falls.
The mystery guy showed up again and Damon suggested that Elena pose as bait to get the vampire in the open to kill him. Elena agreed against Stefan's better judgment but the trio went to the 50's dance together. Damon tried to make peace with Bonnie but was unsuccessful. He asked Elena to dance and she accepted—for herself and Stefan. When Elena saw a hooded man, Stefan went after him. He wasn't the guy who was stalking her however, after she left alone, she received a phone call from actual stalker. He threatened her to leave the dance. He attacked her but Stefan and Damon arrived. The brothers questioned him about why he was after Elena but wouldn't accept that it was for fun. Noah told them that they could open the tomb using Emily's grimoire but because he had been invited in Elena's home, Stefan staked and killed him.
Stefan promised Damon he would help him find Emily's grimoire but told Elena he had to stop Damon from getting Katherine out of the tomb. Damon didn't trust Stefan and asked Elena as a second judgment, requesting an honest answer. Damon asked Elena, and when he asked her she lied to him and he believed her. She and Stefan found the book in Giuseppe Salvatore's grave but Damon arrived and decided to get the book by threatening to turn Elena into a vampire. He succeeded. Stefan took Elena home, but when he found out Anna was in the house, he found Elena had gone missing. He asked for Damon's help, but Damon, still upset with him, gave well-wishing for Elena's death, driving Stefan to ask Sheila Bennett. The Bennetts decided to open the tomb so Damon could get Katherine and leave. To ensure that they wouldn't close the tomb on him, Damon took Elena in with him as insurance.However, Damon realized Katherine wasn't inside the tomb and was devastated. Elena gave him a hug and told him she was sorry. When he found out Katherine escaped the tomb and never cared about him, he started drinking and partying to drown his sorrows. Stefan and Elena put together the pieces of Isobel Saltzman and how she was Elena's birth mother and Damon had killed her. Elena was shocked and angered by this and confronted him; Damon was surprised. She later learned that Damon had turned Isobel into a vampire. Elena continued to resent Damon for what he had done to her mother and was convinced by Stefan to go on a double date with Caroline and Matt but the date was cut short after the couples walked in on Damon making out with Matt's mother Kelly Donovan.
Damon and Elena had to work together to rescue Stefan from the tomb vampires, who kidnapped him for revenge.Once Damon tried to save Stefan, Ms.Gibbons was compelled to not never ever let Damon inside the house.Then he comes out while Elena comes out the car saying we need to find another way to get Stefan then Damon tells Elena that he knows there has to be another way to get Stefan (he puts his hands on her face) and goes to Alaric for help. Damon had Elena wait in the car for her own safety, but being stubborn and worried, Elena went to the house Stefan was held captive and came across Damon, who was angry that she had disobeyed him. They managed to save Stefan who convinced them to spare Harper before leaving. While Damon fought off vampires with Alaric, Elena tried to get Stefan away and fed him her blood to strengthen him, frightened by the ferocious side of him when he violently staked Frederick.
Elena then asked for Damon's help because of Stefan's instability.Elena invites Damon over and asks him how long Stefan will be this way. While perusing her room, Damon tells her that John is in the town council, also suggesting that since Stefan was ‘under control’ so long, the Damon-like monster inside was fighting its way out.At the Founder's Day Kick-Off Party Elena asks Damon if he knows what his brother’s been up to, and he says he’s been too preoccupied with hers, expressing concern that Jeremy is asking so many questions.He then gives her a rose.
In Miss Mystic Falls Stefan told Elena that he stopped drinking human blood, but it wasn't true in fact he had a fridge full of stolen blood from the blood banks. At the Miss Mystic Falls Pageant Damon told Elena that Stefan was still drinking human blood, and when Stefan found out that he told her he was furious, and he fed on a girl who was taking part in the pageant, Amber Bradley. Meanwhile, Damon filled in for Stefan, as Elena's escort, which Elena didn't seem to mind.As they were dancing she smiles at him like wow. Later Damon told Elena that Stefan was gone, there was blood upstairs and one of the girls was missing. Bonnie overheard their conversation and followed them in the woods, where they discovered Stefan feeding on the terrified Amber. Bonnie used her powers to stop Stefan. At the Salvatore Boarding House later that night, Elena visited a hungry and angry Stefan, where she injected him with a needle full of vervain, so Damon could lock him in the cellar. While Elena sits down by the cellar. Damon sits down too. After an errand with Alaric, Damon sees Elena in the couch writing in her diary and puts her foot up so he can sit down then puts her foot back on his lap, patting it.
Elena and Damon seemed to bond more and more, and Elena was shocked when her mother, Isobel Flemming told her that Damon was in love with her. On Founder's Day, she asked Damon to stop with his little flirty comments and the eye thing that he did, while she also asked him not to make her regret being his friend. Damon later stood up for Elena with Jeremy, when he told her to go to hell. When he went to inform Elena and Stefan about the tomb vampires' attack, he grabbed Elena's hand, which Stefan didn't really seem to like, but had no time to comment about it. When Stefan noticed that Damon was missing, he went to save him from the fire with Elena following behind. She insisted on going in, but Bonnie stopped her, and with a spell, she tamed the flames inside so Stefan could rescue Damon.
At the Grill, Stefan showed concern about her friendship with Damon, and she said that she cared about Damon, but she only loved him. Later at Elena's house, Damon opened his heart to her and showed the human side of him, and as a thank you for saving him, he kissed her, thinking that she was Elena, unaware that the fake "Elena" was in fact his vampire ex-girlfriend Katherine.
Elena went to the hospital to see how Caroline was holding up, when Damon suggested that he give her his blood so she would heal quicker, Elena didn't want this, given the risk that she could become a vampire, but Bonnie told him to do it for Elena. She and Damon spoke, Damon bringing up "their" kiss, but Elena had no clue what he was talking about. He then realized that it wasn't Elena he kissed, but Katherine. Elena couldn't believe that he actually thought she would kiss him. He and Elena went back to Elena's house where they found Stefan getting himself off the floor; he had confronted Katherine who hadn't fooled him. Damon revealed to Stefan that he meant to kiss Elena but ended up kissing Katherine, but Stefan was angry at him anyhow.
Elena had to stand between them to stop them from fighting. Damon came across Katherine who had a smoky kissing scene, then who gave him the devastating blow of never loving him and he drank himself to the point of being drunk. He went to Elena's room and tried to force her to admit that there was something between them. Desperate, Damon kissed her but Elena denied his kiss, telling him that while she cared about him, she loved Stefan. Damon, furious, broke Jeremy's neck in the drunken hopes that he would turn, horrifying Elena to tears. Stefan arrived not too long after this and consoled Elena, who confessed to him her hatred of Damon. Jeremy soon came back to life due to John's ring, which relieved both Elena and Stefan.
When Caroline was turned into a vampire, Damon said that she'd have to die, and Elena was revolted by the idea of killing her. She and Stefan defended Caroline, and during the Mystic Falls Carnival, Damon was on the verge of staking her when Elena shielded Caroline, angrily protesting that she was her friend. He then gave up, saying that she was responsible for whatever would happen because of Caroline from now on. He then left.
Damon and Elena had to go on a trip to Duke University with Alaric to find Isobel's research on Mystic Falls to see if she had found anything on werewolves. Stefan didn't like Elena going with Damon, and Elena gave Stefan a passionate goodbye kiss in front of Damon, making him uncomfortable. While rifling through Isobel's office, Vanessa Monroe tried to shoot Elena with a crossbow. Damon, seeing the attack, sped in front of Elena and took the arrow instead, Elena then pulled the arrow out and Damon still tries her to get to like him by bringing his arm to her shoulder. Then she and Damon introduced themselves to Vanessa. She then gave her vervain, saying that Damon was a "first-rate jackass," knowing full well he was listening.
Later, when the they were about to leave, Damon gave her a book that was labeled "Petrova," saying that Katherine was originally from Europe —being born as Katerina Petrova— and asked her if they could be friends again, to which Elena simply thanked him. When they arrived at her house, Elena asked him if he saw the ring, and he admitted he didn't and that he got lucky with the ring, given the fact that he could have truly killed Jeremy. Elena thanked him for his honesty, but told him that he'd lost her forever, outraged that he'd kept information about Katherine that she needed. Damon, hurt and angered by this, bitterly told her that she and Katherine had a lot more in common than their physical appearances before leaving her alone on the porch.
When he and Stefan were outed as vampires by Mason to Sheriff Forbes, they were injected with vervain and brutally interrogated about their ability to walk in the daylight. Elena and Caroline intervened, and Caroline killed the deputies, exposing her vampirism to her mother in the process. Damon was seemingly on the verge of killing Caroline's mother, but chose to spare her, much to everyone's relief. After a talk during which Elena learned that Stefan was going to drink human blood again in order to be able to protect her, she told Damon that what he did to Caroline's mother was the person that she'd become friends with. He then told her that deep down, she knew that Stefan needed to drink the human blood, before leaving. Later on, he provoked Katherine, which resulted in her compelling Jenna to stab herself. She survived, but this incident caused Elena to break up with Stefan, worried that as long as she and Stefan were together, Katherine would hurt or possibly kill everyone she loved. When she was leaving, Damon confessed to her that he'd goaded Katherine and a tearful Elena said that Katherine had won.
Not long after saving her from Rose and Elijah, she and Stefan shared an embrace, although she acknowledged Damon, smiling and mouthing "thank you," to him, showing her gratitude towards both brothers. Before returning her vervain necklace, Damon professed his love to her and kissed her forehead. He then tearfully compelled her to forget the conversation, and gave her the necklace.
Stefan tells Elena that they have no choice to get the Moonstone from Katherine to save her life.But she says, "What about Klaus?" Then Stefan say we will deal with him after the Moonstone.Elena says"Is that before or after he kills everyone I care about, including both of you (pointing at Damon and staring at Damon). Then Damon gives her a What you care about me face.Then Damon learned from Rose that Elena planned to surrender herself to Klaus, he was infuriated and went to Elena and ordered her to leave Slater's house. She angrily refused, determined to protect her loved ones from Klaus, and attempted to punch him. However, when Cody and a group of other vampires, including the believed-dead Elijah, arrived to collect, Damon tried to keep her from being taken and was surprised when Elijah killed the others. When they went back to her house, they argued about her decision to sacrifice herself—only to be interrupted by Jeremy telling them that Stefan was in the tomb. Elena was devastated and Damon prevented her from running inside.
In By the Light of the Moon, Damon comes to Elena’s house to be one of her ‘babysitters,’ as Bonnie casts a spell on Elena to keep her in the house. He tells Jeremy that Bonnie’s dealing with the moonstone, as he’s on ‘Elena Patrol’ and Caroline’s with Tyler. Damon later tells Jeremy to keep an eye on Elena as he leaves. He taunts Elena about not being able to leave. She’s angry with him, but Damon continues to have a care-free attitude.
In The Descent, Damon asks Elena to watch over Rose after she has been bitten Jules, but he rejects the fact that he’s upset about Rose’s impending death. After he kills Rose, Elena confronts him. But he snaps at her saying that he feels emotions, and that ‘it sucks.’ He feels guilty because Jules was coming after him, not Rose. Elena hugs him anyway, and Damon’s eyes begin to visibly water.
In Daddy Issues, Elena informs Damon that John has revealed to Jenna that he is Elena's biological father. Damon makes sure Elena is okay, then jokes about killing John. Elena is somewhat relieved to see that Damon does not trust John either, so she goes with Damon to confront John at the Grill. When they arrive at the Grill, Elena tells Damon to "be the better man" and to "not do anything stupid". Not surprisingly, Damon sarcastically tells her that stupid is more fun. When Jenna tries to get him to date her friend, Andie Star, he blows her off. Elena has watched the whole interaction and when he reaches her, she tells him that he shouldn't be rude. He then replies that his steering away from all women is in the best interests of women everywhere. He and Elena eye each other for a moment, but then Elena's phone rings. Elena briefs Damon on the situation and forbids him from killing Tyler. He tells her to stop assuming he'll do things just because she asks.
In The Last Dance, Damon and Elena share a dance at the 60's decade dance. Damon is lucid and comforts Elena while they dance, drawing a few giggles despite their serious situation. Later Elena confronts Damon when she learns he knew Bonnie had to die and slaps him. After Damon explains what happened she apologizes to him. He then tells her that if it means Elena will be safe, he would not mind letting Bonnie die, even doing it himself, as he will always choose Elena. Elena doesn't say anything for a moment but then wishes him goodnight and leaves.
In The Last Day, Damon is lying in bed listening to Elena, Stefan, and Elijah talk about the sun and moon curse. He approaches after Elijah describes how powerful Klaus will be, wondering why they can’t just kill him beforehand. He suggests that they go through with their original plan to let Bonnie kill him, channeling the power of the witches, but Elena objects because a spell that powerful would claim Bonnie’s life. Damon replies sarcastically, saying he’ll write her a good eulogy. When Elijah reveals that Klaus will truly have to kill Elena to complete the ritual, Damon becomes aggressive, rejecting that the Elixir will work and positive that Elena won’t survive this new plan. Elena later comes to his room to assure him that he won’t lose her, he forces her to drink his blood as a more definitive way of making sure she’ll come back to life – as a vampire. Stefan intervenes and the two have a violent fight, which ends in Damon stabbing his brother through the stomach with a large piece of wood. He leaves angry once again, speaking briefly to Elijah in the sitting room. Elijah tells him that vampire blood nullifies the Elixir, pointing out that Elena will never forgive him for what he’s just done.
When Elena was dead in The Sun Also Rises, Damon carries her, saying, "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." As Elena comes back to life, Damon makes sure she’s not in transition, and he’s extremely relieved that she’s alright.
In the last episode Damon goes to Elena’s house to earnestly ask for her forgiveness, not because he wants it, but because he needs it. Unaware that he’s dying, she asks for more time to consider forgiving him, and Damon agrees wholeheartedly. Later Stefan tells Elena that Damon is dying as he is bitten by a werewolf. At the “Gone with the Wind” screening Elena finds Damon and drags him away, but as she does Damon gets confused, mixing the present with the past, when he chased Katherine through some woods. He remembers begging Katherine to feed him her blood so they could be together forever. Back in the present, he tries to bite Elena as she begs him to stop, explaining that he is hurting her. Damon suddenly appears to return to the present, but collapses. Elena cradles him, while also covering her neck with her hand.
Elena takes Damon back to his room, where she watches over him. Damon worries that he’ll be dangerous like Rose, but Elena refuses to leave his side. She gets into bed with him and holds his head to her chest, where Damon talks about the bad decisions he’s made. He tells Elena to apologize to his brother for him, admitting that he deserves to die, after everything he’s done. He apologizes to Elena again and tells her that he loves her, which brings tears to her eyes. He then tells her that she would've liked him better as a human, to which she responds she likes him now, the way he is. She kisses him just before Katherine arrives to deliver the cure, which she says Stefan paid for by giving himself over to Klaus. She tells Elena that it’s alright to love both Salvatores, because she did. She leaves and Elena and Damon remain to contemplate what’s going to happen to Stefan.
Elena and Damon's relationship begins to take off to a whole new level, where Elena starts to let Damon in. In The Birthday, a voice behind Elena says good morning. She turns around and sees Damon naked, she throws him a towel so he can cover up, annoyed by his inappropriate behavior. Later that night at the boarding house as Elena gets ready for her party, Damon walks in and teases her. Elena assures him that she isn't going to get upset and that she is determined to have fun.
He quips "It's your party, you can cry if you want to." She smiles and he says that he got her something. He opens a little box and reveals he has found her necklace. Elena is thrilled saying that she thought she would never see it again, Damon helps her put it on and they go down to the party.
Later, that night he goes to his room and Elena is there. Furious she asks him why he didn't tell her that he was tracking Klaus' victims, to which he replies that the victims are Stefan's and not Klaus'. Elena refuses to accept Stefan's killings as his own and pleads with Damon to stop talking about Stefan like that.
Damon replies angrily that she should stop looking for Stefan because he's not going to return, at least not in her lifetime. Damon looks and feels guilty and walks out of the room when Elena starts to cry.
In The Hybrid, Elena asks Alaric if they can take a hike through The Smoky Mountains in Tennessee, which he agrees to after she says that she's going with or without him. During the hike, Elena and Alaric are talking near a small cliff with a pool of water under it when someone randomly pushes Elena into the water below. When she looks up, it turns out that Damon was the one who pushed her into the water. She asks Damon how he found them and why he was here.
He thanks Rick for the tip, and tells Elena to get out of the water because there leaving. Elena, being stubborn, refuses to get out of the water. Damon gets in to the water they talk and she convinces him to stay for a while, he reluctantly agrees on the condition that they leave before the full moon Damon adds that unless she wanted to relive their romantic kiss on his deathbed.
The three then continued their walk up the mountain as Stefan hears Damon and Elena talking. They run across Ray and he attacks Damon, but Elena throws him the Wolf's bane bomb and Ray passes out. They tie him to a tree where he wakes up and begins to turn even through the moon is not full. Damon tries to hold him back, Elena worried informs Damon that they have to get out of there now. They run until Elena trips and looks up and a werewolf stands right in front of her eyes. Damon distracts the werewolf from Elena and runs, while the werewolf follows him.
Alaric tells Elena they should keep running she hesitates saying they can't leave without Damon and that it's her fault that he's there. Alaric says it's his fault and convinces Elena to keep running. Later, Elena sees Damon get out of the car and asks him if he's okay, he assures her that he is fine. Elena asks if she can have a minute to appreciate that Damon is still alive. Later, Elena walks in to her room Damon gets Elena to confess that she cares about him letting her know he will get Stefan back but he just wants to make sure she remembers how she feels about Damon once that happens.
In The End of The Affair, Elena was just waking up when she rolls over and puts her arm on him. As Elena quickly wakes up, she realizes Damon is there, she screams and covers herself with the blanket. Elena is irritated by Damon when he says fine. "Don't come with me to get Stefan." Damon tells her where he is. Then says "Start packing." Damon then goes through her underwear drawer. Elena quickly snatches her underwear and she gets ready. Elena and Damon take a road trip to Chicago to convince Stefan to come home again, when he says to Elena he no longer cares for her or loves her anymore making her become heartbroken. Later while they are in the car driving home Damon asks her if is she is okay. Elena responds "Just drive".
In Disturbing Behavior, The two cook chili together, and seem to be getting closer. However Elena is still unsure what to think of their relationship. Angry over the recent events Damon snaps Alaric's neck and goes after Bill, leaving Elena with Alaric. After Caroline helps Elena secure Alaric they go looking for Damon in the Lockwood house. The girls find him feeding from Bill Forbes's neck thankfully Caroline is able to stop Damon from killing her father. Elena is furious for Damon's reckless and stupid behavior while he thinks that Elena wants to change him into someone he's not. After their argument Damon leaves town with Katherine to see if there is anyway to kill Klaus.
In The Reckoning, Damon barely makes it back to Mystic Falls in time to save Elena form Klaus. He finds out that Klaus took her to the local hospital so he can drain her of all of her blood in order to make his Hybrid army. Damon arrives in the hospital's parking lot to rescue Elena. Klaus tries to stop him however Damon is able to scare Klaus off by mentioning he knows that Mikael is looking for him. Horrified Klaus flees town, taking Elena's blood with him. After dealing with Klaus Damon quickly goes to Elena's hospital room and gently carries her back to the boarding house.
Later on in the night while in the boarding house recovering from being drained of most of her blood Damon gives Elena a glass of bourbon to help her forget everything she experienced. He goes on to say that if she wishes it he can compel her. She however refuses the compulsion and instead wants to remember everything that transpired.
In attempt to lift her spirits Damon reveals that he stole back her necklace. Deeply upset, Elena shows no interest in the necklace and devastatingly confesses to Damon that Stefan is truly gone forever. Damon tries his best to comfort her he gently places his hand on her thigh and says that he should never of left town and pledges to never leave her again Elena is somewhat comforted by his words and smiles slightly. Their intimate moment however is interrupted by Stefan walking into the living room saying that Klaus ordered him to watch over Elena until he can return.
In Smells Like Teen Spirit, Elena has started training with Alaric so she can protect herself against Stefan should he try and attack her again. Later on while she is lifting weights in the gym Damon appears and playfully mocks her efforts to make herself stronger.
Elena brushes off his teasing and says that she wants to lock Stefan up so she can cure him of his blood addiction. Damon is extremely against the idea doubting if it will work at all. He gently takes her in his arms and puts his fingers on her skin below her ribs, to show her where a vampires most vulnerable point is.
Despite his reservations Damon nonetheless pledges his loyalty to her and agrees to help. Later that night at the bonfire as part of Elena's plan Damon tries to distract Rebekah by flirting with her she figures out his intentions and stakes him in his stomach annoyed for trying to fool her.
At the end of the episode Damon gently tends to Elena's wounds she got during the car fire in the school parking lot. Damon and Elena both admit to each other that they were half faking their feelings at the bonfire. Elena only pretended to be drunk and was a bit jealous of Damon flirting with Rebekah while Damon admitted he wasn't interested in Rebekah at all. He apologizes to both Elena and Alaric, and remains loyal to both of them.
In the beginning of the episode Ordinary People, Elena is shown training with Damon he jokingly calls her sloppy and then mockingly bites her. Elena's new idea in order to help Stefan and herself is to get information out of Rebekah about the Original Family. Damon is hesitant about this and worries that she could get hurt. However Elena is confident that Rebekah won't hurt her and reassures him that she will be fine. Later that day Damon calls Elena from a bar out of town and confesses to her that he let Stefan out of his prison. Elena is angry at him for this but before she can say anymore Damon promptly hangs up, irritating her.
That night after Elena is done speaking with Rebekah she goes to her bedroom to find Damon already laying on her bed. She is mildly annoyed at his presence but doesn't throw him out. As Elena goes to settle down for the night Damon says he was expecting her to lash out at him for letting Stefan out of his cell. She says that she is tired and doesn't feel like yelling at him. Damon tells her that although Stefan still doesn't have his humanity he is now on their side.
Elena is somewhat comforted by this and tells him that she may of gotten Rebekah to help them as well. Elena then says that she knows that she will need his help to bring Stefan fully back. She says confidently “I think you’re going to be the one who saves him from himself. It won’t be because he loves me; it will be because he loves you.” Elena then says that she will tell him everything else in the morning and falls asleep with Damon by her side both content for the time being.
In Homecoming, Elena, Damon, Stefan and Mikael all discuss the plan to kill Klaus, Elena is worried but the other three assure her. Later that day Elena and Damon are cleaning and organizing supplies in the Salvatore bathroom; wolfsbane grenades and stakes dipped in Vervain. As she goes to take a part a grenade in order to refill and clean it, Damon gently but firmly takes it out of her hands worried that if it were to explode she could get hurt. Elena voices her concern over their plan. Damon is also worried but tells her that he has a secret back up plan. When she asks what it is about Damon quips "If I told you it wouldn't be a secret now would it?" He again assures Elena to trust her. Stefan comes in and says that he needs a new tie for the Homecoming dance.He voices his doubts about the plan saying that whenever they come up with a plan someone's (Elena's) humanity always gets in the way.
Later that night after Elena daggers Rebekah Damon appears and congratulates her on a job well done. Elena feels extremely guilty but knew Rebekah had to be sidelined because they couldn't trust her to not go Elijah on them at the crucial moment. Damon quips impressed "Hey, I'm not judging you, it's very... Katherine of you." Elena replies saying,"Not the way to make me feel better about myself, Damon."
Elena is very concerned that Stefan was right about someone's humanity getting in the way, and since she felt bad for stabbing someone in the back (literally), she worried she is the weak link if they can't trust Mikael or Stefan; they need a better plan. Damon says he knows what to do, but Elena has to trust him, which means she can't have any part of his plan when things are set in motion trusting him she agrees.
After their ruined plan Damon and Elena are next seen in the living room of the boarding house. Damon is feeling extremely angry that their plan didn't work seeing as they had thought of everything; Mikael turning on them, Klaus having Hybrids they even put Katherine in Elena's place so she wouldn't get hurt. Elena manages to calm Damon down. She takes his face in between her hands and says soothingly "We'll survive this, we always survive.. trust me." Damon feels a bit better. He says sadly "We're never getting Stefan back you know that don't you?" Elena says resolutely "Then we'll let him go, okay we'll have to let him go."
In The New Deal, Elena approaches a drunk Damon and asks if he is okay. They flirt for a while but are interrupted by Klaus. Klaus wants Elena and Damon to find Stefan in order to get his coffins back but when they refuse, he gets a hybrid to run over Jeremy who has been off vervain due to Tyler's influence and has been compelled by Klaus.
Jeremy needs a normal life so Elena asks Damon to compel him to leave town for a long while and never think twice about it. Elena feels guilty for compelling her brother and Damon calms her down saying that she just saved his life and Jeremy is lucky to have her. Elena thanks him for everything and says "I don't know what I'd do if you weren't here". Damon feels guilty and Elena said "Guilty for what". Then he says "For wanting what I want" And then Elena says, "Damon"..Damon says "I know, brother's girl and all". Elena looks kinda sad. Then he leaves but in the same moment comes back saying "If I'm gonna feel guilty about something I'm gonna feel guilty about this" and he kisses Elena on the porch. Elena does not pull away but reciprocates the kiss.
In Our Town, it`s the day after the kiss, and Elena and Damon are dealing with the kissing last night differently. Damon is all happy, but Elena is acting really strange.
After Stefan kidnapping Elena, and then leaving her on the Wickery Bridge, Damon picks Elena up and drives her home. They are talking about Stefan`s method of getting Klaus' attention. Elena think it sucked, but Damon thought it was necessary to deal with Klaus and the coffins. Damon asks if she is okay, and strokes her chin. Then, she says, "You can`t kiss me again..." Damon says "I know." but they still stare intensely at each other."I can`t. It`s not right" Elena says, and drag his hand away form her chin. No, it`s right. It`s just not right now." Damon corrects. They say goodnight to each other, and Damon walks away from the porch, while Elena stares at him.
In The Ties That Bind, Damon gives Bonnie and Elena the information about Abby. Damon wants to go with them to visit Abby, but Elena doesn't want his snarky commentary along for the first time Bonnie sees her mom in 15 years. Bonnie doesn't know why Damon and Elena are behaving so differently. Damon explains that they kissed. Elena tells Stefan about her kiss with Damon but tells him she's not telling him because she's guilty it happened, instead because she feels guilty that he doesn't know.
In Bringing Out The Dead, Stefan tells Damon that he loves Elena and Damon responds, "So do I".
In Dangerous Liaisons, Elena is surprised to receive an invitation to a formal ball, and when Damon and Stefan hear the party is being hosted at Klaus' newly renovated mansion, they both insist on attending the event with her. At the elegant ball, Damon tries to protect Elena from the Original Witch, Esther, saying that it is to dangerous to go and he won't let her. Damon then offers his hand to Elena then they share a dance. During the dance, Damon compliments Elena saying that she looks stunning if it isn't obvious.
Later, Damon finds Elena and tells her they are going home but Elena refuses. Damon says he is just trying to protect her and tells her that he is mad because he loves her. Elena then says that his love is a problem and Damon is severely hurt. Elena realized she made a mistake and tries to tell him that she didn't mean it. He finds a new way to cope by sleeping with Rebekah.
In All My Children, Elena finds out about Damon's latest indiscretion(sleeping with Rebekah) and gets annoyed. She gets frustrated with her friends for not agreeing with her on how they should react about the Original family's internal power struggle. Stefan and Damon are given an ultimatum from Elijah that puts Elena in danger so they turn to Meredith and Alaric for help which ends up being a terrible choice, the killing of Abby Bennett. Turning Abby Bennett into a vampire was supposed to safe Elena, Damon's plan.
In 1912, Damon tells Elena that everything is back to normal as he is mean and she hates him. She tells him if he keeps pushing people away, he's going to end up alone. Later Elena comes to a new understanding of the path her life has taken: she realizes that one of the main reasons that she fell in love with Stefan and felt safe with him was because he seemed like he could never die unlike her parents. As for Damon, she admitted to Matt that Damon had snuck under her skin and she hadn't been able to get him out of it. Matt told her that that was what happened 'when you fall in love with someone.' Elena didn't contradict him.
In Break On Through, when Damon informs Elena of Stefan’s latest struggles, she reaches out to Stefan to help her save a friend in danger, in hopes that it will help bring Stefan even closer to his humanity.
In The Murder of One, Elena comes to save Damon from Rebekah and offers her blood, they almost kiss but it's just a dream controlled by Rebekah onto Damon's mind. Later Stefan tells Elena that she is also in love with Damon but she denies it and he asks her to tell him honestly that she feels something for Damon. She tells him that she doesn't know what she feels meaning that she has feelings for Damon as well.
In Heart of Darkness, Elena and Damon go on a road trip to Denver to see Jeremy and to get his help to contact Rose's ghost to discover who she was sired by. When Elena is lying in bed later that night, Damon is watching out the window while drinking, as she is gazing at him. He then notices this and lies next to her. She asks why he can't express his goodness and humanity, which he replies that when someone has good in them, people expect good, and he doesn't want to live by anyone's standards, he then reaches and laces his fingers through her hand. Overwhelmed and breathless, Elena scurries out of the motel room to the balcony.
Damon then follows her outside, and Elena, with her back to him, desperately says "Don't", he then replies "Why not? Elena". She then takes a deep breath, and viewers see Elena in those few seconds experiencing an overwhelming inner-turmoil as she battles between her morals and her desires. The latter wins out and she then turns around and strides over to Damon and kisses him. They kiss passionately and lustfully, as Damon, showing no self-restraint, then pushes her up against a pillar and continues to kiss her furiously. Their passionate moment is interrupted by Jeremy's arrival, who awkwardly tells them that Rose had found Mary where (the woman who sired Rose) was staying. Though Elena is mortified by the arrival of Jeremy, she has a hint of a smug smile, seeming somewhat satisfied yet flustered by what her and Damon had just done. When the trio arrive at Mary's house, Jeremy stays as Damon and Elena go inside. They are then attacked by Kol, and Damon gets becomes livid when Kol hurts Elena.Seeming satisfied he has inflicted as much dismay and damage as possible, Kol leaves and Elena then helps Damon with his injuries.
He then proceeds and places his hand on her cheek affectionately, to check that she is alright. Elena then backs away seeming unsure of herself. Damon asks what they are doing and Elena then says that Stefan thinks that she has feelings for him, Damon asks if she does, and she replies that she doesn't know. Fed up with her ambiguity and dishonesty, Damon then figures out that the point of the entire journey to Denver was for him to answer her doubts by doing something reckless. She then replies, clearly upset, that he constantly sabotages himself every time when they hit a bump in the road. Damon, then replies that he isn't going to help her anymore with her feelings, and that she now has to sort it out herself.
Later, as they are driving home, Jeremy is sitting in the back sensing tension in the atmosphere. Rose appears and makes it clear that she doesn't want her presence known to Damon and Elena. She then says she knows Jeremy wants to protect his sister from Damon, fearing she'll get hurt, but says that because he's so young, he doesn't see what she sees. She remarks, that not only does Elena help bring out Damon's humanity, and make him a better man, but Damon also changes her as well; he challenges her, surprises her, makes her question her life and her beliefs. Their relationship is truly dynamic. She then goes on to say that Stefan is different and his relationship with Elena is pure love, and that he will always be good for her, but Damon could be the best thing for her, but he could also be the worst. This leaves Jeremy quietly stunned.
In Before Sunset, Damon and Stefan join forces with Klaus to save Elena and Caroline from Alaric.
In The Departed, Elena calls Damon and tells him she's going back, not just for Stefan, but also for Caroline and Tyler. Damon asks if it was just between him and Stefan, who would get the goodbye. Elena tells him: "I love him, Damon. He came into my life at a time when I needed someone and I fell for him instantly. No matter what I feel for you, I never unfell for him." . Heartbroken, Damon says that he gets it that its always going to be Stefan. However Elena says she can't think about always, all she can think about is right now. Elena says things may be different if she had met him before Stefan. Elena assures him that she will see him soon and they say their goodbyes. Damon then remembers how he had, in fact, met Elena before Stefan. Damon saw her there on a road and mistook her for Katherine. He told her about what she really wanted: a love that consumes her, passion and adventure, and even a little danger, before compelling her to forget meeting him.
At the start of Season Four, Damon is with Elena and Stefan in Elena's room, explaining to her that she died with vampire blood (Damon's blood) in her system and that she is now a vampire. He talks to them harshly and tells Elena to feed or die.Later on, she sees Damon in her room, but realizes she's remembering the scene from Rose, where Damon tells her he loves her and he doesn't deserve her then compelled her to forget. She then seems to be shocked by this.
When Damon nearly kills Matt, Elena attacks Damon and saying, "Leave him alone!". She tells him she remembers everything, including the fact that she met him first. She eludes to the fact that it wouldn't change anything, but she has to take it a bit further. She asks him what he would have done if he was in Stefan's position and he tells the truth only Damon would tell: he'd let Matt die to save her because he's selfish. He's so selfish, that he'd take someone else's life to give Elena the one she wanted: a human life. And that single factor changes everything. Damon has always been selfish and destructive, but one great reason Elena's answer had to be Stefan hearkened back to the time when Damon just couldn't understand why she'd choose death over vampirism. He tells her "I would have saved you in a heartbeat; no question. You would have gotten to grow up and had the life that you wanted, the life that you deserved. I wanted that for you, Elena, and I would have gladly given it to you and let Matt die because I AM that selfish."Now that he gets that and Elena remembers everything, the love triangle has once again found a way to ignite even further.
In Memorial, Damon tells Elena that she's a vampire now so be a vampire. In the Grill, she asks for him for help because she can't keep the animal blood down. He takes her to the bathroom and offers her his blood and she ultimately agrees to feed on his blood but he also tells her not to tell Stefan because it's "personal".
On the way to the church, Damon gets a call from Elena telling him to hurry as she needs help because she needs a change of clothes and that someone's outside the bathroom while she's throwing up his blood. He gets there in time before Connor attacks. He brings her the blood bags that she asked him to bring but as she starts throwing it up, he comforts her. As they are having a very close moment, they are interrupted by the church bells and Elena tells him she has to get in the church. But Elena and Damon are still closer than ever, and the sexual tension between them has even increased as Elena's emotions were heightened.
In The Rager, Elena is in Damon's room "supposedly" looking for bourbon but he knows that she is lying as she wants the white oak stake. He starts undressing in front of her and then asking her if she’d like to stay for the show and she walks out. Later, Elena has hallucinations of Damon, he'd told her the reason she was seeing him was because she knew she was more like him than Stefan now, that was Elena admitting it to herself. If she has to feed from the vein to survive, she needs Damon to teach her how.
Near the end of the episode, Elena fed on Matt again and would've killed him this time had Damon not shown up to stop her. He compelled Matt to forget about Elena going overboard and told Elena he was going to teach her the right way to be a vampire. Then he comforts her.
In The Five, Elena and Damon tag along with Bonnie on a college road trip. Bonnie is going to meet with the professor who took over Grams’ classes, while Damon teaches Elena to hunt. Damon picks out a blonde girl for her, and Elena catches up with her after class. She compels the girl, but as she is about to bite into her wrist, Elena sees a photo on the girl’s phone of her and her baby sister. She can’t do it. Luckily there is a frat party that night, so finding someone to feed off of shouldn’t be hard.
At the party, Elena immediately finds the boy she wants to eat. She lures him away easily and drinks deeply. Damon supervises, and begins to worry that she is drinking too much. She stops herself, and proudly hugs Damon. But she wants more. Back on the dance floor, the two split up and drink from anyone unlucky enough to dance with them. Elena and Damon then come together, both with bloody mouths, and dance together seductively, on a blood high. Elena catches sight of Bonnie and immediately feels guilty for enjoying herself.
As Elena says, “I should be here with Stefan.” Damon steps outside in time to hear that last bit. Bonnie accuses him of wanting Elena to go over the edge. He argues that she needs to learn to revel in being a vampire. Not hating herself and enjoying it will be the only way she, like him, can make feeding fun and not go nuts and kill hundreds of people. Damon walks away hurt and Elena begins to cry as she realizes what she has done to him. He accompanies her home and she apologizes for letting things get out of hand at the party then accidentally hurts his feelings by saying she hates thinking that he’s right about what a vampire is supposed to be. “Because you don’t want to be like me,” Damon finishes.
In The Killer, Damon came to see Elena because Stefan was dodging his calls. We found out Elena hadn't told Stefan about dirty dancing with Damon after she got high on blood at the Murder House Party. Damon knows she's in a shame spiral filled with newbie vampire remorse, but Elena still wouldn't admit it to anyone but her diary. When Stefan wouldn't answer a call from Elena's cell, they realized something must be wrong. Damon later found Alaric's map of the tunnels that conveniently provide an entrance to the Grill. Since Connor doesn't know she's a vampire yet, Elena wanted to offer to trade herself for the hostages. Damon rightfully thought that was a stupid idea because she's not ready to go up against a professional killer. A mock fight ensued that ended with Elena straddling Damon on the bed. She said Jeremy was the only thing holding her together, and he promised they'd get him out. After Stefan had to vervain Damon, he woke up and she wanted him to go to the Grill, but Stefan had taken his day ring, so he couldn't. Elena decided she was going, and Damon told her to use the fact that Connor doesn't know she's a vampire to get as close as she could before making her move. When Elena was digging a grave to bury Connor in the woods, she sobbed when Stefan and Damon showed up. But she's angry at Stefan for lying to her.In We All Go A Little Mad Sometimes, after Elena kills Connor in the last episode, she starts having hallucinations and nearly kills Jeremy. She calls Damon, not Stefan, for help, because she doesn't trust Stefan anymore but still trusts Damon. "What am I going to say to him?” Elena asks the next morning. Still bloody from the night before, she paces and waits for Jeremy to wake from the dead. Damon replies, “How about thanks for not ditching the family ring even after it drove Ric crazy.” Damon repeatedly suggests that Elena call Stefan to come help her deal. She refuses, saying, “He’s been lying to me and hiding things from me. He compelled Jeremy to forget God knows what.” A second later, Stefan walks in. Damon admits calling him. Meanwhile, Damon cleans the kitchen and Elena tries to shower off the memory of stabbing Jeremy. But she hallucinates that the water turns to blood.
After getting dressed and going downstairs, she hallucinates Connor again and begins to dash for the door causing Damon to go after her. When she runs out the door Klaus grabs her and speeds off. Elena breaks out of the room Klaus imprisoned her in and Stefan sends Damon to find her. He finds her on Wickery bridge, and tries to talk sense into her, but she doesn't listen still heeding the ghostly presences, until Jeremy kills a vampire and breaks the curse. After he does the deed, Jeremy stands there and watches as the hunter’s mark inch up his arm. Just as it does, the sun rises over the horizon and Elena’s skin starts to sizzle. When it seems like she might get the death she no longer wants, Damon, not thinking twice, grabs her and dives into the water, saving her from the sun.
The next day, Elena wakes up in her bed noticeably lighter and better. Damon has been waiting in her room looking after her."You know what they say about teenage suicide,” he jokes. “Don’t do it.” He found Elena's daylight ring and put it back on her finger. Elena tells Damon that the last 24 hours were like a really bad dream. She thanks him for saving her. Damon sits on Elena's bed and they take each other's hands, sharing a moment. But, his nobler sentiments get the better of him and Damon explains Stefan's actions over the last few days to her and that he was lying in order to help Klaus find the alleged cure for Elena. Later that day, Stefan comes to the house have a talk with Elena. She asks him why he sent Damon, to find her and save her instead of him, her boyfriend. He explains to her that since she turned Elena trusts Damon but not Stefan. Stefan understood why Elena was driven to Damon when Stefan was a Ripper, but now he doesn't. Elena explains to Stefan that since she turned, Damon and her have something more. Her feelings for Damon have amplified. Stefan listens, and he does not seem surprised. “Before, when I was the Ripper, I understood why you cared for him,” he says. “I mean, I practically drove you to it. But now, I can’t do this, Elena. Not anymore.” Elena replies, “I know.” They sit on the porch together, having broken up for good.
In My Brother's Keeper, after Damon learns of Elena and Stefan's breakup, he visits her and Caroline, whilst they help April pick a dress for the pageant. Viewers see Elena's self-consciousness as she hastily tries to fix her dress and hair when Damon walks in the room; similar to an awkward teenager. At first Elena and Caroline were dead set on the blue dress, being the safer choice over the red, but when Damon states that the red one would look better, and asks for Elena's agreement, she reconsiders by saying "the red is pretty." Caroline shoots daggers at her, wondering aloud why she changed her mind and whatever happened to the safe choice being the good choice. When Damon leaves, Elena runs after him saying they need to talk. Damon says he knows about the break-up and isn't sorry about it. Elena asks him if he knows the reason as to why they broke up. Damon doesn't and states: "I'm sure it had something to do with you acting weird". Elena gives him a meaningful look and tells him the reason is, "You." Damon is dumbstruck and gives her a small, almost disbelieving smile. They share a long moment, looking at each other, but Professor Shane interrupts. The following pageant is full of shared looks and meaningful glances rife with sexual tension.
After the pageant, Elena, having to get away from Jeremy as he's having nightmares about killing his sister, moves into the Salvatore house. Stefan, decides he can't be there and heads to Caroline's, leaving Elena and Damon alone. Elena reflects, over a glass of whisky, about how she probably sucks at being a vampire, and how everyone wants to fix her and change her back into who she used to be. But, Damon says that he's never seen her more alive. Elena smiles at this. She reminisces about dancing with Damon at the Miss Mystic Falls Pageant exactly a year ago. She shyly admits that she had wanted to share a dance with him today. He twinkles at her and extends his hand as an invitation and she accepts, dancing with him in front of the fireplace. It gets progressively more intimate as Damon twirls Elena away and then back towards himself and their lips meet.
From soft and slow their kisses get more and more passionate. Damon lets Elena take the lead. She knocks a lamp over as she pushes him against a wall, rips his shirt open and kisses him, running her hands over his chest as Damon looks equal parts surprised and awed. Damon reverses their positions and presses himself into her, her right leg wrapped around him, kissing each other wildly. The scene cuts to Caroline and Stefan saying that Elena's feelings for Damon might mean that she is sired to Damon.
When the scene cuts back to Elena, in nothing but her lingerie, is straddling and kissing a naked Damon in his bed. The scene intercuts with Damon and Elena making passionate but tender love, alternately kissing each others chests and mouths. They switch positions and Elena looks happy, laughing with Damon, while he seems awed beyond belief. They move in unison, looking into each others eyes and the episode ends with them cradling each others faces in a loving kiss.
In We'll Always Have Bourbon Street, still in bed, Damon is shown to be happy while Elena kisses him passionately then they make love again. Damon sends Elena off to school with a request that they wait just one day before they blab about their new relationship to Stefan. "It's our time right now, and it never has been before," he pleads: "Just one day!" and she agrees. When Elena heads off to school, Stefan shows up to talk to Damon.
Stefan feels a pressing need to tell Damon about the sire bond, and to his credit he isn't insanely gloaty about it, but you know he's feeling pretty relieved on the inside. Damon isn't buying, however. "Really, Stefan?" he sneers. "You two idiots can't stand that she's happy because of me." Well, yes, but Stefan may be right as well. He challenges Damon to test Elena by giving her a blood bag again. Damon reluctantly agrees to the deal, though he tells his brother that, when her body rejects the blood, "Your apology better be epic." He heads to the school and when Elena sees him, she follows him. He gives her a blood bag and "I can't believe this, Damon! I don't have to hurt people anymore!" She's thrilled, Damon less so. She hugs and kisses him before going to class.
When going to New Orleans with Stefan, Damon learns of the sire bond. The link between vampires seems to be formed out of love. When a human loves a vampire, and is turned by that vampire's blood, they experience the sire bond, and do their best to please their sire. Whereas Elena learns from Tyler, The sire bond does not influence feelings, only actions. Damon finds out the way to break the sire bond is for the sire to tell the one with the sire bond to forget about them and move on with their life.
Damon, like the secretly good bad guy he is, goes home to dump Elena. But Elena already knows about his motives, thanks to Caroline spilling the beans about the siring thing. "I've changed, and so have you, Damon," she says. "And I'm happy. It is real, I know what it is. Please don't do this to me."This is exactly what Damon wants to hear, but the end result is this just makes it harder for him to do what he's expected to do. "I'm not the good guy, I'm the selfish one. "I don't do the right thing. But I have to do the right thing by you."he says. She takes his hand and places it on her heart. "Does this feel wrong?" she asks as she strokes his face. He doesn't answer, but it certainly doesn't seem to be wrong. Then she places her hand on his cheek and repeats the question. The episode ends with Damon confused but he didn't break up with her. This scene is similar to a moment they had in Smells Like Teen Spirit.
In O Come, All Ye Faithful, Damon wasn't going to release Elena from the sire bond, he did the next most decent thing: He refused to sleep with her. They woke up, fully clothed, in the same bed. He was already feeling guilty. He knows what he should have done. Instead, he got up to change his shirt. Elena insisted this feels real to her and essentially dared him to send her away. Damon said what he really wanted to do was throw her back in his bed and never let her leave. She told him to do it. Sadly, Elena's phone rang. "Saved by the cell phone," Damon said. Bonnie wanted Elena to meet her at the Gilbert family lake house, where she's trying to teach Jeremy not to kill Elena. Elena asked Damon if he wanted to come.
At the Gilbert Family Lake House, Jeremy was chopping wood and he got a little testy when Elena and Damon pulled up. He said they shouldn't be there. But he trusts Bonnie, and she said they’re there to help him. So was Professor Shadypants, as Damon calls Shane. The lake house is now in Jeremy's name, so he had to invite Elena in. He did—so he could try to stake her. After trying to deprogram her brother, Elena told Damon how strange it was that the last time she'd been there, she was so in love with Stefan, and now that's barely a memory. Was that the sire bond's work, or her being so happy with Damon that she's forgetting about Stefan? That conversation gave Damon an idea: Professor Shane should have used someone other than the person Jeremy wants to kill to attach Jeremy's "detour feelings" to.
"You. I feel that way about you," Jeremy said to Bonnie. The sweet, awkward smiles Jeremy and Bonnie shared. Outside, Shane and Elena talked about her relationship with Damon. He said he'd once loved someone too much, too—his wife and son had died and he'd been trying to figure out a way not to miss them. Damon interrupted them to threaten Shane's life (again), but Shane saved himself by saying he could lead them to the cure because he's already been there.
Shane had to do some quick thinking of his own: Damon told Elena his theory about Shane having killed the pastor and 11 others in that gas explosion. Shane said the pastor had lost his wife to cancer and sought him out for supernatural assistance. But the pastor was too far gone. Elena said she trusts Shane. That discussion got interrupted by Jeremy and Bonnie, who were ready to prove Jeremy could play nicely now. "Jeremy, remember the detour. Choose the right path," Shane said, as Jeremy walked toward Elena with a wooden stake in his hand. Damon stepped in between them, and Jeremy looked at a smiling Bonnie and handed the wood to Damon. Then he reached Elena and hugged her.
As Damon watched Elena and Jeremy decide which Christmas ornaments to bring back to their house, Damon sat outside on the deck and watched her. Elena took out plastic mistletoe and wanted a kiss, but Damon wouldn't do it. He said it was good to see her normal like that with her brother. He wants that for her. The truth is, of course, that Damon wants that with his brother, too. He misses celebrating Christmas with Stefan, which used to be their favorite holiday when they were human. Damon was ready to do the right thing: He told her she’s gonna go home. He’s gonna stay there with Jeremy and teach him how to hunt, protect himself, and kill vampires without her. "I’m setting you free Elena. This is what I want. This is what will make me happy," he said.Later, we saw Jeremy thank Bonnie and hug her goodbye. Bonnie was going to drive Elena home. Elena told Damon she was prepared to fight him on this, but suddenly, every part of her body was telling her she needs to get in the car and leave him. She kissed him goodbye. Simple and gentle, they clearly felt the kiss, but she was very confused about the intense push to leave him still. Damon was surprised by the kiss, but still saddened that he had to send her away.
In After School Special, Rebekah takes Stefan, Caroline, and Elena captive in the school library. She asks them some questions about the cure and Stefan reveals that Elena slept with Damon and that she is sired to him. Rebekah then turns to Elena and compels her to tell them the truth about Damon. Elena says that being with Damon is unpredictable, and that it makes her feel happy and free. Later that night she calls Damon and they talk about Jeremy. As Damon starts to hang up, Elena tells him that she realized something about them today. She goes on to tell him that she is in love with him. After that, Damon asks her to get in her car right now and come to him. They hang up and Damon looks up at the sky, amazed that he is finally feeling reciprocated love for the first time in his life.
Soon following in Catch Me If You Can, Elena was coming to the lake to see Damon. She arrived just in time to save Matt from another vampire, and inside they went when the line of vampires approaching. Elena was naturally upset with Damon, but she agreed to let him stay with Jeremy and go hunting while she took Matt home. After a while, Elena heard from Jeremy that Kol had Damon. She went to see Klaus to beg him to call off Kol. She convinced him that they were all on the same team to a point. But the problem was that Damon was compelled by Kol to kill Jeremy.
Later, Damon went to see Elena and asked where Jeremy was. At the Grill, she said, checking on Matt. Damon said he should go apologize to Jeremy for being tough on him. At the Grill, Jeremy senses something was up with Damon when they came eye-to-eye. He started after Jeremy, and Elena called Damon's name and he stopped -- for a second. He told Elena that Kol must have compelled him because if he finds Jeremy, he’ll kill him. Elena still needed to save Jeremy, so she called Stefan. Rebekah answered his phone, and Elena knew he'd hear her even if he wouldn't talk to her. She told him the situation and said if he cares about the cure or Jeremy, he’d come help. He didn't answer so she hung up on him.
Elena caught up to Damon and tried to tell him that he can resist the compulsion because she loves him, and he loves her, and he'll do anything for her. "Sorry, Elena," he said and continued the chase. When he found Jeremy, Damon again did the most decent thing he could. "Shoot now," he told Jeremy. Jeremy fired a shot, and Stefan pushed Damon out of the way. "Hey brother, long time no see," Stefan said. And he snapped his neck. Then, he looked at Elena. “You’re welcome," he added. Damon was taken back to Salvatore Mansion and drained of most of his blood to weaken him. He couldn't even get off his back. He wanted to see Elena, but Stefan said they can't let him do that because with the sire bond, he'd be able to get Elena to let him out. Stefan's plan: Damon stays in there until they find the cure and the sire bond and compulsion are broken. Then Elena and Damon can do whatever they want. Upstairs, Stefan ran into Elena and told her she couldn't see Damon because she'd let him out.
At the end of the next episode, A View To A Kill, Damon was reunited with Elena now that he’s no longer compelled to kill Jeremy, and Stefan arrived home with Silas’ headstone. Elena assumed Rebekah was daggered so they just needed to get Professor Shane and they’d be set -- but Stefan said he didn't dagger Rebekah because she’s on their side. How could he trust her? Damon was more than happy to tell Elena that Stefan had slept with Rebekah. Elena had nothing to say until the brothers started bickering, and then she told them to stop. “Why don’t you tell her to calm down, Damon. You've managed to use that sire bond pretty well so far, haven’t you?” Stefan said. Damon punched Stefan.
Arriving at the island, Damon declined to tell Elena if he’d take the cure when it’s found. Later, Shane made a comment about Damon having the most to lose when they find the cure, Elena had to assure him that her love for him won’t change. Then she kisses him and he hugs her. She clearly wants him to take the cure. Shane tried to tell Damon he should leave the island rather than watch Elena find the cure and choose Stefan. He assumed Damon wouldn't kill him because then Bonnie would die when she did the spell to access the cure. But Damon doesn't care about Bonnie, he told Shane. And right before Damon snapped his neck, Elena arrived to stop him. She freed Shane and told him to stop messing with her friends. Damon's anxieties about Elena were coming to the forefront. He was terrified that her love for him might be entirely because of the sire bond. If that's the case, then as soon as she gets cured, she won't love him anymore. Rather than face that possibility, he protected his emotions by pushing her away. He rejected Elena and the possibility of taking the cure himself -- though that latter may be genuine, as he's been a vampire for a long time and had a lot of fun with it."You know, I used to miss being human. Now I can’t think of anything more miserable on earth," he told Elena.
In Down the Rabbit Hole, Damon plans on getting the cure for the girl he loves. Stefan and Elena found Damon and Rebekah while and Vaughn fled through the passage. Stefan sent Elena on, and he stayed behind to try to help Damon.
In Stand By Me, Damon stayed on the island to try find Bonnie. When he found her, he and Bonnie took a flight back to Mystic Falls. Later when they came back, Elena went upstairs in Jeremy's room and she realized that Jeremy was dead. Damon,who followed her, tried to calm her down but without any success. She pleased him to take Jeremy body downstairs which he did. Elena went in the kitchen and took a bottle of gas and started pouring it around the house. Stefan, Damon, and Caroline were watching in surprise.
Elena went near the fireplace and took a match. She lighted the match and was ready to drop it on the floor and set the house on fire. She started talking about her mother, her dad, Jenna, Alaric, Jeremy, and John who used to live there and about the house which is full of memories of people she loved and died. Suddenly the match burned her finger and she let it fall but luckily Damon caught it in time. Elena broke down on the floor and started crying and shouting about the pain that she couldn't handle anymore. Stefan told Damon to help her. He sat on the floor next to her and hugged her. He told her that he can help her. He told her to turn it off that this was what he wanted for her to do. Elena stared at Damon for a little while with tears on her eyes and then she turned off her humanity. Next on the porch, Damon and Stefan were talking about Elena. Damon told Stefan, "Humanity means nothing when you don't have anyone to care about". Stefan replied, "She had you". Later they went back in. Elena took another match, lighted it and let it fall on the ground. The house started burning and they left home with Jeremy and Elena's memories, including Elena's past burning into flames.
In Bring It On, Elena was laying in the middle of the street(similar to what Damon does), waited for a car to stop, and fed on the (vervain-free) driver until Damon showed up and told her to show some restraint. "I thought this was supposed to be fun," no-humanity Elena pouted, throwing the woman to the ground. Caroline thought school would be a good idea, and Damon told Elena it would make him happy (and not to feed on anyone), but Elena rejoined the cheerleading squad and fed on the (vervain-free) competition, taking the ribbon she wanted. And then things just kept getting worse. Caroline tried to talk to her, but it became clear the sire bond wasn't working; without her humanity, she had no feelings.
Later, Elena and Caroline were fighting, Elena had almost killed her and Damon had to intervene when Elena was a little too close to maybe staking Caroline for comfort. Elena told Damon that she had enough of people telling her to feel when she felt amazing.She asked him if he wants for her to be back like the scared little girl who coudn't admit what she wants,meaning that she would've chose him instead of Stefan if she wasn't scared. She reminded him that he had wanted to be with her and wanted him to be honest that he liked her like this. Damon had sneaked Elena out of the house and decided it was time for another road trip. Brings back memories. We see them in Damon's car, heading to New York, the city that never sleeps.
From Because the Night onward, the relationship between Damon and Elena seems to be broken beyond repair due to a conflict of interest: Damon wants Elena to take the cure at all cost, whereas Elena wants to find the cure first so she can keep the Salvatore brothers from making her take it. Elena will stop at nothing to reach her goal, and seems to no longer care for those that she once considered her friends. She only teams up with Rebekah because they have the same goal and because Rebekah will protect her from Damon and Stefan. While Damon and Elena are in New York, it is also shown that Elena now sees Damon as a mere tool that will help her reach her goal of finding the cure, as she uses him to get away from New York so she can go after Katherine, who has the cure.
In American Gothic, Elena and Rebekah steal Damon's car but Damon and Stefan eventually track Elena down. Later, Elena tells Stefan and Damon that she no longer wants the cure and has no intention to take it. She then asks Stefan and Damon to back down and stop trying to make her take the cure, to which they refuse. She then kills a waitress and tells them that until they stop trying to forcibly cure her, she will kill many more people.In Pictures of You, Stefan tells Damon once Elena gets her humanity back, Damon will help her deal with all the emotions she's repressed since Jeremy's death and Stefan will leave town. At night, Damon and Stefan picked Elena up in a limo and Damon gave her a corsage. Both Damon and Stefan walked her down a red carpet walkway which was lined with large screens flashing photos (of Elena and Matt, and Elena and Jeremy) that were meant to tug at Elena's heartstrings. It started to work, so Elena moved inside. Damon stopped her from drinking from a flask and he started working the "I'm your boyfriend, and we're at prom, how romantic!" angle on her. She wasn't biting and she told him he's nothing to her and that she'd only told him she loved him when she still had her humanity because of the sire bond, leaving him heartbroken. Then Elena danced with Stefan in front of Damon which made him jealous.
Later Elena tried to kill Bonnie and Bonnie used her magic which made Elena throw up Bonnie's blood and her bones being broken. Stefan and Damon stopped Bonnie from killing Elena. He hugged her while she was begging Bonnie to stop. Bonnie realizing what she had done left. Elena gave Damon a meaningful look. Damon helped Elena get up and as Damon held her Stefan vervained her. Damon and Stefan brought Elena to the basement of the Salvatore Boarding House. Damon told Stefan that he saw the fear, which in fact is an emotion, in Elena's eyes. Stefan replied that they would make her life a living hell as it is the only way for her to feel again.In The Originals, Damon and Stefan discusses about how Elena seems to be more resistant to blood-starving than they expected. Damon asks how long is it going to take before Elena starts becoming emotional, to which Stefan replies that it is probably going to take a lot more time.
Later, towards the end of the episode, Damon goes to see Elena in the cell of the Salvatore Boarding House where the two brothers hold her captive, and tell her that she "looks terrible", implying that she is starving for blood, to which she replies that Damon doesn't care about her. Damon then goes on to tell her that he does care, but that she doesn't, which is the problem, and that it needs to change. He then gives her a blood bag. However, Elena quickly spits out the blood as she realizes that it has been mixed with vervain. Damon then asks her how she feels about what he just did to her (giving her the blood bag with vervain), and implies that he and Stefan are going to torture her until she turns her humanity back on. Elena tries to escape with super speed, but is blocked by Stefan. She tells them that if they want to "play games" to determine who has the most willpower between them, they shall see who is going to "break first". Stefan then closes the ceil's door.In She's Come Undone, Damon was inside Elena's head, making her think she was walking on school grounds talking to Caroline, who'd just been named valedictorian. He wanted to show her all she's missing out on. The Salvatores had her locked in their version of solitary, a tall safe. Elena was brought upstairs and tied to a chair without her day-ring. Stefan opened the curtains and she suffered the punishment. Damon was using a fire extinguisher to put out the flames on her arm. She told him she was going to kill him. Stefan didn't hesitate to pull back the curtains far enough to burn her face the next time. Elena was burning again, and this time, she launched a verbal assault on Damon. She told him he was right -- she never loved him, it was just the sire bond. Elena broke free from her singed rope constraints, pulled back the curtains herself, and set herself on fire. The brothers stopped her. They love her too much to ever really hurt her, Elena said, so what does she have to be afraid of?
Damon couldn't understand why Elena wasn't doing what every other vampire eventually does -- turn on her emotions. Stefan reminded him it's because Elena has NOTHING to come back to. If they weren't going to hurt her, they had to bring in someone who would. Stefan thought of Katherine. After Katherine was done with Elena, she reminded him again that EVERYONE thinks Elena will go back to Stefan once she gets her humanity back. Stefan burst in to say Elena was gone. Katherine hadn't locked her in. She wanted to see her escape and raise hell, which would be more entertaining. Damon decided to take Matt with him as bait.In the woods, Elena kicked Matt because she wanted him to wake up so she could feed again. The Salvatores finally stepped in, and then Damon had enough: He told Elena that he was going to kill Matt. She called his bluff, and he snapped Matt's neck. Elena went to Matt, believing he was gone, and when Damon showed her that he was wearing the resurrection ring, he said she was experiencing joy that her friend wasn't dead. The memories came back to Elena: What she'd done to Matt, Caroline, Bonnie, and that waitress that she actually killed. She started crying, broke the glass in the truck's window, and just generally freaked out. Damon tried to calm her down but she wouldn't listen. Stefan told her he knew this stage: She had to focus on one thing inside of her that makes her strong and latch on to it. She had to find the thing inside of her that makes her want to live. Back at Salvatore Mansion. She got it now: shutting off your emotions is a cheat. Things have happened that can't be undone, she said. And she needs to do something about that. Turns out, the reason she had to live was to kill Katherine, who she blames for everything -- ruining their lives, bringing Klaus to Mystic Falls, killing Jeremy.
In The Walking Dead, Damon is avoiding Elena and Stefan's attempts to use himself as a guiding example fall short because he had the same killing compulsion with Klaus as Elena has with Katherine. When discovering that Bonnie is going to drop the veil, Stefan teams up with Caroline to search inside for Bonnie, while Damon and Elena look outside. Mostly, she just wants to know where Katherine is. He thinks she needs to let it go. "Behind your rage there is a tidal wave of feelings," Damon says. "Killing Katherine is going to let it all in." Elena disagrees, so she stabs him in the stomach and runs off.
Near the end of the episode, Elena starts to apologize to everybody -- Bonnie, Stefan, Damon -- but Damon tell her it's ok and to spend time with Jeremy before the veil is put back up. Damon and the real Alaric, load stone Silas into the trunk of a car, they plan to drop him into the ocean. But first, Alaric gives Damon something he found in Silas' pocket: the cure. "Get the girl," Alaric tells him and smiles.
When Graduation finally arrived, Elena wanted to talk to Damon about their relationship but before she could, Damon gave Elena the cure as her graduation present. When Elena wouldn't take it -- because then the Hunters would kill people -- Damon knew the sire bond hadn't resurfaced when she got her humanity back. Damon thought Jeremy would help him convince her, but Jeremy said it was her choice. He accepts Elena as a vampire now. That's nice. Elena then noticed Damon wincing in pain and told him to take off his shirt. "Elena, there are children present," he cracked. She saw the wound from Vaughn's wooden-bullet gun hadn't healed. He told her that bullet was laced with werewolf venom -- and the hunters were dicks. With Klaus in New Orleans, the only hope was for Damon to take the cure and become human so he didn't die. That's what Elena wanted. But Damon said he was so motivated by Elena's save-the-world speech, he wouldn't do it. He gave the cure to Vaughn and told him they were off to dig up Silas. Damon didn't want to become human, so if he was going to die, he'd at least distract Vaughn.
Elena was freaking out about Damon leaving until Stefan told her it was a stall tactic. He said the bullet was only laced with werewolf venom, so Damon had time. Jeremy made Elena go to graduation but she was still shown to be worried about Damon. Later, Vaughn was about to kill Damon until Alaric stepped in and saved him. Alaric phoned the others ask Stefan whether he should watch Damon die or force-feed him the cure. But Klaus arrived in Mystic Falls in time and Damon was cured.Elena asked Damon if he was alright now and he told her he was fine then she slapped him which made Alaric proud and Lexi laugh. Damon was standing in front of the fireplace and said he wanted to apologize, but then realized he wasn't sorry. Yes, he'd rather die than be human, both because he didn't want to age and because he didn't want to age while she remained the same. He's selfish, and no apology would encompass all the reasons he's wrong for her, he said. Elena said she wasn't going to apologize either then. She's not sorry she met him. Not sorry that in death, he's the one who made her feel more alive. Not sorry that even though she knows it'll be the worst decision she's made, she's in love with him. "I love you, Damon," she said. And he kissed her. This time it was real. Elena truly loves Damon and is fully devoted to him.
As Elena is leaving for college, Damon promises her that he will take care of Jeremy and that Whitmore is only a few hours away and so she doesn't need to worry.She shares a passionate goodbye kiss with Damon, and before making her final exit, she opens the door again to give Damon another quick kiss.
Later, Elena calls Damon to tell him about an unexpected human roommate who has just arrived. Damon agreed with what Caroline had said earlier: compel her ass out the door, but Elena doesn't want to just make Whitmore the new Mystic Falls. Damon ends the discussion abruptly because he finds Katherine waiting for him in his living room.Damon and Elena checked in with each other later over the phone, and he tells her nothing about Jeremy's car accident, expulsion, Silas, Katherine, or anything else that had happened that day.When Jeremy comments about him lying, Damon replies that he doesn't want Elena to come running back to Mystic Falls and that he will figure all this house because he wants her to be happy and enjoy her college life.
In True Lies, Elena called Damon to tell him about the humiliation from Professor Wes Maxfield's class and Damon asked her if she'd pressed him for information. "At least tell me you used torture," he said, reminding her that she's dating a reformed serial killer.Elena said "Stefan?" because she thought she saw him. "Probably mope at him," Damon cracked. Before Damon could explain it wasn't Stefan, Silas told Elena to turn off her phone and she did. Damon is desperate to find Elena at the bonfire to tell her that Stefan is really Silas, and she’s busy drinking, trying to drown her sorrows over her Damon and Jeremy problem. Damon finally finds Elena, and when she gets him alone, she feeds him vervain, and readies to kill him, with Silas’ compulsion. Of course, Damon gets out of it, and snaps Elena out of Silas’ trance, by telling her to think 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. This shows how much they really are in love when they're embracing while having a disagreement.
In Original Sin, Elena wakes up in bed next to Damon telling him that she had a bad dream about Stefan. Damon is annoyed but eventually asks her to tell him about it. Elena tells him how she saw Stefan burning in sun in front of a bar but doesn't know where, then Katherine makes her presence telling the name of the bar and saying she had the exact same dream. Then Damon and Elena along with Katherine go to find the bar.
After reaching the bar Damon compels the owner to tell what happened with Stefan, she tells them the whole story and tells how Qetsiyah threw him into a truck. She mentions how she knows who's truck it was and directs them to the hut. Damon and Elena then go on separate ways as Elena decides to save Katherine from Nadia and 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.
After finally finding Stefan they take him back to the boarding house where Elena praises Damon for looking out for Stefan but Damon doesn't respond. 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, Elena and Damon try to remind Stefan of his past. Later Damon gets a text from Jeremy for meeting him alone and Damon leaves Stefan with Elena. Jeremy confesses to Damon about Bonnie's death and Damon is shaken by it. Meanwhile Elena admits to Stefan about being with Damon when he tries to kiss her which upsets Stefan and he vanishes. 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 and leaves the house. Elena tells Damon that they need Bonnie 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 visits Elena at her college to say yes to her Whitmore Historical Ball's invitation.Elena has been avoiding him since three days as she is feeling guilty because she was enjoying her life while her best friend was dead.Elena kisses him goodbye and leaves for her class.They attend the ball dressed as Anne Boleyn and Henry VIII.At the ball,Damon teases her by saying "Lady Anne Boleyn. Now who in their right mind would cut off a head so gorgeous?" To which Elena replies "You, my King. My not so loving husband." Then Damon tries to make her have some fun but Elena heads to investigating Megan's death.
Later at the ball, they find a desiccated Silas who has turned cold and grey and is unable to move because of Qetsiyah's spell. Damon and Elena find him and take him back to the Salvatore house. At the house, they are telling each other about their respective missions of the day and how they failed. Then,Katherine arrives at Salvatore house and she is happy seeing that Silas is gone but Damon gives a devious smile and Katherine realizes why he has called her. Damon then feeds Katherine's blood to Silas while Elena watches and they think that she is dead. But soon she wakes up leaving Damon and Elena stunned and confused.
In Handle with Care, Damon and Elena were at Salvatore Mansion snuggling by the fire and debating how good a day it was about to be when Silas made his entrance. "Good morning, frenemies," he said, ready to get his death on.Elena wasn't sure they could trust him to trade his life for Bonnie's. “You’re kinda evil. No offense,” she said. None taken. He assured her that he was in: He just has to find the anchor, destroy it to destroy the other side, die, and finally be at peace. He knew roughly where the anchor was. Silas was in such a great mood: When Jeremy appeared with his crossbow, Silas knew how excited Jeremy must be. They were all on the same side for the moment, so Damon told Jeremy to "Put the damn crossbow down, Pocahontas." All the doubting made Silas feel ganged up on. Silas then refused to let Elena come along as she looks exactly like his true love, Amara. Elena refused as she wanted to go as well then Silas used his magic on the crossbow to shoot Elena in the leg which upset Damon as he hurried to her side.Elena was concerned about why Stefan would be fraternizing with Tessa. When she phoned Damon and Silas made sure Damon told her about how he'd maybe kinda sorta snapped Stefan's neck a couple of times, Elena was furious. Tessa informed Damon that she'd purposely lured Elena to the cabin so she could use her as leverage. Tessa wanted Damon to kill Silas before he found the anchor. If he didn't do it before sundown, she'd kill Elena. It might be cathartic, she said, because Elena has the same face as Amara. Elena managed to escape with Stefan's help. Later, Damon told Elena they had to protect Amara now that she's taken the cure and is human again.
In Death and the Maiden, Damon and Elena are finally able to bring Bonnie back to life with the help of Qetsiyah who makes Bonnie the new anchor to the other side.
In Dead Man on Campus, Elena invites Damon to her first college party but first he decides to confront Wes about his lastest actions and what he's up to. Later in the night, Elena knew she needed to phone Damon and make sure he wasn't going to murder Wes. Elena showed up and saw Jesse feeding off of Damon. "He's gonna tear my head off, Elena. Please," he said. She finally staked Jesse. Caroline appeared, just in time for Jesse to die. Damon tried to tell her Elena had no choice.
In The Cell, Elena goes to see Aaron since Damon never came back from interrogating Wes and she's worried. He takes her to the Whitmore House and Wes appears out of nowhere and vervains Elena in front of Aaron. Elena wakes up in a cell next to Damon in the basement of the Whitmore house, and she finally learns about Damon's Augustine days. Turns out, he was in that very same cell for five years in the 50s, getting tortured surgically every day by the Augustine doctors and getting only enough blood to heal back up to do it all over again. They did it all under the guise of researching how vampires regenerated on a cellular level, but it was just sadistic. They would take out pieces of his organs, cut into him over and over, just to watch him heal. He made a friend, Enzo, who was a soldier in Europe during WWII that was shipped to America for 10 years of Augustine torture. He told Damon the way to survive was to picture his revenge and that will get him through the day.
Damon promises Elena that he'll get her out of there after she agonizes over how her father could have been one of those sadistic doctors. Damon 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.He continues to tell her more about the past. Every year on New Year's Eve, the Augustine docs let the vampires out of their cells, though still in a cage with vervained bars, for a party. Dr. Whitmore let the guests drink Damon and Enzo's blood to demonstrate how vamp blood worked. And that's how Enzo comes up with an escape plan: one of them will drink both their daily rations of blood for an entire year to gain strength and get revenge the next year on New Years Eve. Enzo lost the rock paper scissors game, so Damon got to drink the rations everyday, saving only a few drops for Enzo so he wouldn't desiccate. 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, while horrified that Damon left Enzo, forgave him since he left to save himself. It was all about survival, after all.
But then then Damon reveals his dark secret. When Aaron comes down to free Elena and Damon, he makes them confess the truth first. He wants to know if Elena killed his parents, but Damon reveals that it was him. Damon killed Aaron's parents. It was all a part of his revenge plan that Enzo told him to focus on back in the 50s. He decided that he would kill all the members of Augustine and then all the members of the Whitmore family, leaving only one Whitmore alive. Damon would let that person grow up, start a family, and then kill them all except for one, let them grow up and start a family, and do it over and over again. For the past 50 years, he's been sticking to his revenge plan and kept it up even as soon as a few months ago, when he killed someone named Sarah Whitmore, Aaron's aunt. He did this at the beginning of his happy, perfect summer with Elena. It was a weekend trip that she didn't know about. Damon's lost count of how many Whitmores he's killed over the years and there isn't anything to excuse him for his shocking, horrifying behavior. He wasn't killing these people to survive, or to save anyone, or because his humanity was flipped off. was no purpose other than pure, unadulterated revenge.
Damon's been keeping it up even during his relationship with Elena, and she had no idea what was going on. And in shock from hearing what Damon's been doing to his family for the past 50 years, Aaron shoots Damon in the head, upsetting Elena, leaving her shocked. 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 get out of the cell and save Elena from Wes. Damon visits Stefan and tells him they have to go get Elena, but he doesn't know where she is, so they need leverage. They find Aaron and Damon tells Aaron to call his uncle to get Elena back, or Wes gets to try to reattach Aaron's arms. Wes manages to keep Damon busy by sending Enzo, who is revealed to be still alive, after Damon. However Stefan manages to save Elena with Aaron's help.
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 and Elena are having a hard time dealing with their breakup. Damon is spending his time drinking while Elena doesn't want to get out of her bed. Later, they have an awkward moment when Elena returns to the boarding house after learning that Katherine is dying. Stefan encourages Elena to not give up on Damon and convinces Damon to get her back. 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 leave without her.In The Devil Inside, Stefan told Caroline he'd like her to help get Damon and Elena back together. Stefan said he believes Elena makes Damon happy, which means he's not out there killing people. Caroline conceded that point. Then they realized Elena was lying to them about where she's staying. Damon was with Stefan and out day-drinking at the Grill then Caroline met up with them, and Damon found it shocking that she, of all people, wanted to help reunite him with Elena. They all texted "Elena," growing increasingly worried because had heard from her either. Elena found herself held hostage by Nadia and Mia, realizing that Katherine is inside her body as a passenger. She learned that Mia was going seal Katherine's spirit into her body. She impersonated Katherine until she could get away. Later, she finally knocked Mia out and staked Nadia in the stomach and ran. She had the phone, but they'd apparently changed her pin number. They didn't need Elena's body to be there. Mia could apparently finish the spell anyway. Katherine's memories started coming to Elena. Instead, she was running to the party, where Damon, who hadn't been able to get inside the house without an invite, was. Elena threw herself into Damon's arms, but just as they embraced, the spell was complete resulting into Elena being gone and Katherine in full control. Damon launched into a speech about why he wanted Elena back. He said thinking he could change her and make her a worse person gave him too much credit and her too little. She's good, and he needs a little good in his life. Without it, there's an awful lot of darkness. Katherine starts talking and tells him that she doesn't want to be the only thing that he lives for. She doesn't want to worry about what happens if they break up and what he'll do -- like how he tortured Katherine. She said Damon was right to let her go and told him it was over. Stefan heard the breakup; Damon assumed a part of him enjoyed it.
In Total Eclipse of the Heart, on Elena's phone, it was shown that she has many photos of her and Damon while she was still human and some of while being a vampire.
In Gone Girl, Stefan tells Damon about Katherine living in Elena's body and that it was Katherine who broke up with him and not Elena. Damon is obviously angry and wants Katherine dead just like everyone. They lure Katherine inside the Salvatore house and Stefan daggers her with the Traveler's Knife killing her for good. Later Damon along with Stefan is waiting for Elena to wake up. Damon tells Stefan that he plans on telling Elena everything he did in her absence and is ready to face the consequences. 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, Elena is informed by Stefan of her current ripper situation and that she has been sealed in her room by a spell so that she doesn't feed on anyone. Elena instantly calls Damon and they are both 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.
Elena wanders outside her dorm, still coughing up blood and hallucinating. She sees Aaron and thinks it means he's ok, but it's really Damon. Damon 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 he thought 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.
At Jeremy's parent teacher conference, Elena finds out she is not his primary contact and asks then who is. Damon enters saying present and sits next to 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 Elena fantasizes about making out with Damon in a class room. She is snapped out of it by Damon who taunts her that she is missing a incredibly boring presentation. Frustrated with their sexual tension, Elena leaves the presentation saying she needs some air. Elena runs into Liv who almost kills her but Damon comes in time and saves Elena. Damon tortures Liv for information despite Elena's request to stop. Finally, Liv tells them that Elena is the last female doppelganger and that Stefan might soon be the last male and if that happens, the Travellers will come to use Elena. Damon is ready to kill Liv, but Jeremy shows up and says Damon will have to go through him. Jeremy convinces Elena and Damon that Liv knows a lot about the Travellers and will help them in protecting Elena.
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 shush's her and does the selfless/right thing, he takes his hands around her neck then slowly kisses her forehead and tells her Travel safe. Elena then seems shocked by Damon's act of selflessness as he walks away, she then seems upset that he finally let her go.
In Resident Evil, Damon is trying to get over Elena by completely "erasing" her from his life. However, when Elena arrives at the house to find a way to stop her visions about Stefan, Damon is immediately enticed by her. After an awkward chat, Elena suggests they be friends and Damon cringes at the idea. Damon asks Elena about the visions and then grits his teeth as he asks if the visions show her with Stefan and really, really happy. Elena doesn't know how to reply and Damon uncomfortably states that Stefan and Elena are fated to be together.
Throughout the day, Damon and Elena have intense conversations, even though she is having rampant dreams about Stefan. Later that night, Damon drinks outside, "listening to the universe laugh at me," he tells Elena. "We were doomed from the beginning, Elena. We were always going to end up here." She assures him the universe doesn't control anything and the dreams are not real. She then has another vision in which she sees the house address and hence announces where to find Markos. Damon and Enzo go in search of Markos and he explains to them that the doppelganger prophecy is not true and the reason why doppelgangers are drawn together is because of a spell that he casted 1500 years ago because travelers needed their blood.
After Markos stops the visions, Damon returns to having Elena in his room. She tells him that the visions were indeed a fantasy but they weren't real and even though Damon and her are messy and complicated they are real. But Damon replies they are still bad for each other. Elena says she still wants him in her life but Damon becomes flustered and tells Elena that he doesn't want anything to do with her as he can't be friends with her. Elena then exits and returns to Whitmore College.
In Man on Fire, Elena is having a hard time dealing with Damon's decision of no longer being around her. She is having a study date with Bonnie and Stefan when Enzo interrupts them and claims that Stefan is responsible for killing the love of his life Maggie. Enzo compels all the students around them and ties Stefan and Elena with vervain ropes and tortures them. He calls Damon to inform him about the situation and warns him about killing either Elena or Stefan. Damon with the help of Sheriff figures that it was actually him who killed Maggie and not Stefan. Damon then joins them and tries to calm Enzo. He then taunts Elena asking if her and Stefan are study buddies now while she whispers to him "What are you doing". He shrugs and finally reveals the truth to them about killing Maggie.
Enzo is not able to deal with the fact that his best friend killed the love of his life and switches off his humanity. A fight takes place between Enzo and the Salvatore boys and Enzo ends up running away with Elena. Damon realizes that Enzo is going to kill Elena for revenge and goes after them. He finds an unconscious Elena outside Whitmore College and carries her to her dorm room. He lays her on the bed and caresses her face. As she starts gaining conscious he vamps speed out before she can see him. Elena wakes up and wonders how she reached here while staring at the window.
In What Lies Beneath, Damon, Stefan, Caroline and Elena decide to make a trip to Caroline's father's remote cabin to hide Stefan and Elena from the travelers. They take Luke along with them so that he is able to perform an anti-locator spell which will hide them from the travelers. While Elena is unpacking her stuff, Damon visits her and they talk about the cabin and Caroline's father. Damon then mentions how he should be avoiding her and Elena asks him if that is what he still wants. Damon replies "Yes. No. I don't know." Elena offers him an out and Damon asks if she is kicking him out. She repeats his words saying "Yes. No. I don't know." They share a flirtatious smile and the conversation soon becomes awkward when Damon mentions Enzo. Elena is feeling guilty about lying to Damon about Enzo's death by the hands of Stefan and leaves making an excuse.
Later, Damon and Caroline admit to each other about their shared suspicion of Stefan and Elena keeping a secret and decide to play games so that the secret comes out. In the evening, the gang is playing charade and there is still no sign of any secret. Then Damon suggests to play "Never have I ever." It goes around until Caroline says "Never have I ever kissed a Salvatore brother -- today." Then Damon says "Never have I lied about where Enzo is." Stefan and Elena are silent and the evening comes to a screeching halt. Elena gets up and leaves for bed.
While Elena is taking a bath, a ghost Enzo who now has the power of touching things in the real world tries to drown her for revenge. When she's able to come up for air, she screams for Damon. He comes to rescue her and wraps a towel around her. He tries to calm her down while Elena panics about what happened. Damon then wonders why a ghost would wanna attack Elena. She finally admits the truth about Enzo's death. Damon joins Stefan and Caroline and they figure out that drowning Elena was just a distraction, Enzo figured out a way to kill them all. He has taken Luke somewhere making it possible for the travelers to track them.Later, Damon is packing up the car in order to move to a new location when Elena approaches him. He tries to brush her off and warns her to hurry as the travelers must be coming. She apologizes for keeping Enzo's death a secret and he says he doesn't care about her lies. She is confused and asks him why is he behaving like this. He then confesses "Because you were right, Elena. You wanted to protect me so I wouldn't spiral because if I spiraled then it would prove that we shouldn't be together, but--but I didn't spiral. Despite every nerve in my body wanting to break something or hurt someone or do all the wrong things for all the right reasons, I'm holding it together the best I can, for you." Elena smiles slightly to herself and playfully asks if he is still mad at her. He further confuses her when he says "Of course I'm still mad at you because being around you drives me nuts, and not being around you drives me nuts." They stare at each other for a while when Damon finally runs towards her and kisses her passionately. Elena whispers what was that for and he mentions how he had a really bad day and he needed it. He goes inside the cabin while Elena has a brief moment to enjoy the glow when suddenly the travelers arrive there paralyzing her brain and Markos grabs her from behind.
In Promised Land, it has been four days since the travelers took Stefan and Elena and Damon has been desperately searching for them. Later, he gets a call from Stefan who informs him that he and Elena have managed to free themselves from the travelers but don't know where they are. When Stefan tells him that he has Elena hunting squirrels, Damon jokes that Elena will shoot Stefan's eyes. Damon tells him that he will find and kill Markos and asks him to have both him and Elena return home safely. On a country road somewhere, Stefan tells Elena that Damon sounded ready to save the world. When she says she likes that Damon, Stefan tells her that there are different rules for vampires and difficult relationships and if she and Damon want to be together, they should be together. When the travelers are successful in their spell and magic starts to vanish from Mystic Falls, all of the vampires start reverting to their human form and start dying from the same wounds they died as a human. Elena, Damon, Stefan, Bonnie and Caroline plan to meet in Whitmore and travel far away so that they are unaffected from the traveler's spell. When Damon reaches Whitmore, Elena rushes to him and kisses him passionately. When he asks what was that for, she repeats his word from their last kiss, "I had a really crappy day and I needed it". She also confesses that she thought she would never see him again and couldn't think of a worse way to die. They are both enjoying their little happiness when Stefan says that he will wait for Caroline and Bonnie. Damon and Elena then leave in the car together and Elena says her goodbye to Jeremy.
Going into the season finale, Damon and Elena hear of Stefan's death and are devastated by it. They both work together to try to find a way to bring him back. Damon plans to blow up Mystic Fall while Elena and Caroline get Liv to help them with the spell. Damon has to break the news to Elena in the town cemetery that he's the one who will "trigger the explosion" at the Mystic Grill. Elena isn't having it and then asks him the big question. "Do you see a future with me because that's all I see." Damon says he's seen it "since Day 1" asking her to "respect" his choice to sacrifice his life for the others. Then, he makes a promise he probably shouldn't have made: "I will make it back to you. I promise." Then they stare at each other, Elena seems lost in the moment and kisses him passionately and he then promises again to Elena that he will return.
Just as Damon's about to drive through the Mystic Grill in a blaze of glory, Elena jumps in the car. Elena says, "You said to respect your choice. Now you can respect mine." Damon looks somewhat shocked that Elena would be willing to die with him so that they're together rather than let Damon die alone. Seconds later the car plows through the Mystic Grill filled with the Travelers, Damon and Elena give each other one last longing look. Elena is about to tell Damon that she loves him but he tells her he knows. They both die ending up on the Other Side.
Elena is reunited with Alaric and she wants to go find Damon but he tells he that he will go find Damon and that she needs to hurry to Bonnie. Damon wakes up and locates Sheriff Forbes under a collapsed column. Struggling to free it, Alaric comes to his rescue, saving Liz from the clutches of death. Most of the gang arrives to where Bonnie is but Elena refuses to go without Damon. Bonnie forces her friend to pass through, Elena then gets angry with Bonnie asking her "Why would you do that?!" and telling her she can't leave without Damon. Bonnie promises that she'll find him then grows weaker and falls over, which causes Stefan to inadvertently come back to life. Elena then begins to panic, believing that Damon will not return in time and starts to cry, Elena then becomes distraught fearing for Damon's return. Alaric passes through as well, but Lexi refuses to take Damon's spot and takes down Markos. Fearing for her life, Luke stops Liv from continuing on with the spell making Damon unable to return back to life.Elena then rushes to Liv and Luke only to find them gone, Bonnie then appears behind a horrified Elena who says that we have to find them. But Bonnie admits to her that it's to late to save Damon. Elena then begins to fall apart, she then becomes full with denial, not wanting to believe that Damon cannot return, Elena's grief becomes unbearable for herself as she struggles to string together words of significance as she slinks down to the ground and cries. "You lied to me." she says, as ghost Damon appears in front of her. "Even if I wanted to apologize, you couldn't hear me, so I won't." he says, stroking her face, she appears to feel his touch, yet continues to cry, Damon then says to Elena, "You are by far the greatest thing that has ever happened to me...The fact that I got to die knowing I was loved... is the epitome of a fulfilled life...It is never going to get better than this. I peaked." Elena distraught with grief makes one small plea to Damon: "Please, please come back to me." Damon then says goodbye and disappears. Alaric appears and comforts her and says to Alaric "He's gone." A broken Elena then hugs Alaric for comfort and he also begins to mourns Damon's death.
Describing their Relationship
- "This year, she's had a very traumatic roller coaster of life experience and it's changed her irrevocably—and at the center of it all was the die hard belief that she loved Damon, that she loved him more than she'd ever loved anyone."
- —Julie Plec
- "That's the journey, I don't just want to throw them together tomorrow. I'd be sad. I want to see the kiss, I want to see the sweaty palms, I want to see it all go down."
- —Kevin Williamson
- "Because of Damon's feelings for Elena, thinking that, for the very first time in his life that he has a home, Elena is the one who helped Damon find his home and his home is Elena."
- —Kevin Williamson
- "I think that's what makes them as a couple so powerful. Even if the story line is them not dating, it's still a love story."
- —Caroline Dries
So many stories are about love at first sight, but we have to say that the most compelling ones are the ones that take their time with the build up, the thrill of the anticipation, until there’s so much unresolved sexual tension waiting to boil over the brim. That definitely fits Damon and Elena’s love story. He was the narcissistic evil vampire, who came to town to seek revenge on his younger brother, who Elena happened to develop an interest in. When everyone had written Damon off as a bad guy who couldn't be redeemed, Elena - who was unafraid of him and willing to call him on his crap- saw something in him that hinted he wasn't entirely evil. And so there marked the start of a tentative yet beautiful friendship. What’s so great about Damon and Elena is that they’re so true to life. Their relationship didn't happen overnight, it took some time. It wasn't perfect, and there were screw ups along the way. But that ‘way’ lead them to becoming friends and Damon falling for Elena. He’s always saving her from danger and she’s saving him from his dark self.
There’s an undeniable chemistry between her and Damon. We see it in the way they look at each other and the way they dance. Even when they’re fighting, there’s heat there. Even Elena admitted herself that being with Damon consumes her and she feels free.
These guys are more than just a simple love story. For three and a half seasons we've been captivated by Damon and Elena. Despite this, they've managed to gather thousands of fans from around the world and have so many talking about them and wondering what’s going to happen next, which is a true testament to how popular they are and their strong chemistry. They say that true love comes to those who wait and this couldn't be more true for Damon and Elena. It finally happened when she chose him in Season Four.
As the series continued on, Elena and Damon's relationship grew even more stronger leading them to wanting to have a future together.
- Start Up: My Brother’s Keeper (4x07)
- Break Up: Fifty Shades of Grayson (5x10)
- Reason: Damon thinks he is bad and doesn't want Elena to always find a explanation for his actions and defend him, so he lets her go despite the fact that they both are still in love with each other and breaks her heart.
Post Break-Up Sex
- Start Up: While You Were Sleeping (5x16)
- Ended: Rescue Me (5x17)
- Reason: Elena asks Damon to let her go because she believes that when they are together they do bad things for each other and that she can't control herself around him. Damon kisses her forehead and lets her go.
- Start Up: Promised Land (5x21)
- Separated by death: Home (5x22)
- Reason: Damon dies in Home, Elena and Damon did not break up.
- Ironically, the actors who play Damon and Elena, Ian Somerhalder and Nina Dobrev began dating in 2010 and moved in together. However, they broke up in 2013 after three years of dating.
- Elena and Damon and Klaus and Caroline are the most popular couples of the show, however, Klaus has now left the show.
- They both know what its like to be the older sibling as they both have a younger brother (Jeremy and Stefan).
- Damon taught Elena how to feed without losing control.
- Their names are linked alphabetically, D and E.
- Damon has never broken a promise to Elena, until Home when he promised to come back to her but died.
- Some of Elena and Damon's most popular moments include:
- The Miss Mystic Falls dance in Miss Mystic Falls.
- Their kiss in As I Lay Dying.
- Their kiss in The New Deal.
- Their bed and kiss scene in Heart of Darkness.
- Their sex scene in My Brother's Keeper.
- Their respective confessions in Graduation.
- Elena telling Damon that she would still love him even after they save Stefan in True Lies.
- Damon tells Elena that she is his life in Original Sin.
- Their hug scene in The Devil Inside.
- Their break up sex in While You Were Sleeping.
- Their Kiss in What Lies Beneath.
- Their Goodbye scene in Home.
- There's been something between them since their first meeting: “Even before anything happened in our series, Elena had been touched in her soul by this man," Julie says of their clandestine meeting.
- Damon originally had his own room until Elena moved in and they began to share a room. She briefly moved in with Rebekah when she lost her humanity.
- Many cast and crew members have shown their love for the couple.
- Elena and Damon have been on a lot of road trips.
- Elena chose Damon over Stefan at the end of Season Four.
- Alaric, Rose, Matt, Enzo, and Stefan ship them.
- Damon became an Augustine Vampire in Total Eclipse of the Heart, and Elena became an Augustine Vampire in Gone Girl, making them the only Augustine Vampires in existence. Though they're cured in While You Were Sleeping and reverted back to Vampires.
- In the series, Damon is the oldest vampire as Katherine died and The Originals left the show while Elena is the youngest vampire.
- Delena is the nickname of singers, Demi Lovato and Selena Gomez (Delena) who are best friends in real life.
- Delena is the most trended TVD couple on Twitter.
- Elena has talked about a future with Damon twice throughout the series.
- In episode 4X19 of The Good Wife, one of the characters reads a Delena fan fiction. 
- Damon and Elena is endgame in the novel series.
- They won the Vampire Diaries Wiki Award for Best Couple for seasons one, two and four. They were nominated in season three, but lost to Jeremy and Anna.
- After getting to the Top 4 on the WetPaint.com contest and getting many votes, they became the number 1 t.v. couple. 1
- They came 1st in the top 10 couples of 2010-2011. 2
- They came 2nd in the top 10 couples of 2011-2012. 3
- They came 3rd in the top 10 couples of 2012-2013. 4
- They won the poll for the hottest relationship on The Vampire Diaries.5
- They won the hollywood life poll of Fall TV’s 25 Hottest Couples.6
- They won the Hollywood life Thanksgiving poll.7
- They were crowned Prom King & Queen in iVillage'S Pop Culture Awards.8
- They won the poll for the hottest sexual tension in 2010. 9
- They won the Alloy entertainment poll for favorite magazine cover.10
- They won the poll for the cutest tv couple of 2012.11
- They won the poll for tv's sexiest hookup.12
- 2 times winner of tubey's Best Almost Romantic But Not Quite Relationship-2010&2011.13 14
- Damon and Elena's sex scene is one of the hottest sex scenes in vampire history according to Hollywood Life.
- They won the title of the best byte of season 4:best couple in an official poll.15
- In 2013, they won the Eonline tournament of the best tv couple of all time.16
- Their 5X02 ending kiss scene was declared the scene of the week.17
- Damon's epic "You are my life" confession to Elena in Original Sin was declared the scene of the week.18
- Damon and Elena won Favorite On-Screen Chemistry at the People's Choice Awards 2014.
- Winners of TV's best Teen couple poll.19
- Their hug during Elena's last moments in 5X12 topped the scene of the week poll along with The Tomorrow People scene. 20
- They came 4th in the top 10 young ships of 2013-2014. 21
- Their 3X19 kiss was voted as the Steamiest Moment in Eonline's Golden Remote Awards 2012. 22
- In Zap2it's Crushworthy Polls, Elena and Damon has won Most Crushworthy Overall and Most Devastating Breakup. 23
- Elena and Damon's deathbed confession and kiss scene in As I Lay Dying won in EW's 2011 Season Finale Awards: Most Rewound Moment, Top Tissue Moment, Best Kiss, Best Romantic Cliff-hanger. 24
- Damon and Elena's break up and break up sex scene in While You Were Sleeping was declared the Scene of the Week. 25
- They won the poll for epic couple who epitomize true love. 26
- The scene in Rescue Me where Damon lets go Elena won the Scene of the Week poll. 27
- Elena and Damon's heartbreaking goodbye scene in Home won the Scene of the Week poll. 28
- Elena and Damon won these awards in the EW's T.V. Season Finale Awards:
- Damon's goodbye to Elena.
- Unforgettable Line.
- Best Use of Music.
- Most Rewound Moment. 29
- They were crowned Alloy Entertainment's Prom King & Prom Queen 2014. 30
- In Eonline's Best Ever TV Awards 2014, Delena won:
- They won the Best Ship Poll in Telefilm Addicted Awards 2012. 32
- They won the Eonline's Tournament of Young TV Edition 2013. 33
- They won the MTV's Ship of the Year Award 2014. 34