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. 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! 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 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 cell'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 Salvatore's had her locked in their version of solitary confinement, 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. If they weren't going to hurt her, they had to bring in someone who would. Stefan thought of Katherine. 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 Salvatore's 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: 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.
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: 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. Elena then noticed Damon wincing in pain and told him to take off his shirt. 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. 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. Jeremy is living with them which leads to awkward moments when he walks in on his sister straddling Damon on the couch. After the end of summer, Elena is finally ready to go to college and a night before leaving she is seen taking a bubble bath in Damon's tub as he walks around in a towel. She mentions she feels something bad is about to happen and Damon replies its because she is leaving for Whitmore College.
Elena asks him to support her decision but he says that he would rather convince her to stay and kisses her. Damon and Elena's sweet goodbye. Later, Elena calls Damon to tell him about an unexpected human roommate who has just arrived. 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 does Elena and Damon get together?
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. 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. 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,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.
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. 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. At the ball, Damon teases her by saying "Lady Anne Boleyn. Now who in their right mind would cut off a head so gorgeous? My not so loving husband. 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.
Elena wasn't sure they could trust him to trade his life for Bonnie's. No offense," she said. 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. 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 latest 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. She finally staked Jesse.
Caroline appeared, just in time for Jesse to die. Damon tried to tell her Elena had no choice. 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 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.
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: 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: 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. 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 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.
Elena and Damon
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.
Stefan said he believes Elena makes Damon happy, which means he's not out there killing people. Caroline conceded that point. 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. 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.
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 okay, but it's really Damon. Damon gives her Stefan's blood to drink. 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.
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. 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.
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.
In the vampire diaries when do elena and damon start dating - Higholeicmarket
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 Travelers 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. 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 always going to end up here. She then has another vision in which she sees the house address and hence announces where to find Markos.
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. 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. She repeats his words saying "Yes. 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.
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Then Damon suggests to play "Never have I ever. 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. 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 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. Then, he makes a promise he probably shouldn't have made: Just as Damon's about to drive through the Mystic Grill in a blaze of glory, Elena jumps in the car.
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Pair were, respectively, start vampire damon in diaries 35 and 93 to take a video dating start when of themselves start in vampire do on the gaming. Kai tells Damon and he's linked Elena's life to Bonnie's and as long as Bonnie lives, Elena will remain asleep but perfectly healthy. He also tells him that the spell is permanent and any attempt to find a loophole in the spell will result in the death of both Bonnie and Elena. Damon returns to the wedding to find Bonnie badly injured on the floor and Kai's reminder that letting Bonnie die will allow Elena to regain consciousness. Damon tells Bonnie he's sorry and leaves the room.
Kai is irritated that his plan to torture Damon with an impossible choice had failed and, while he's distracted, Damon decapitates him from behind. Damon saves Bonnie's life and they go to the Salvatore boarding house to say their goodbyes to Elena, deciding that they will allow Bonnie to live her life and, when she dies, Elena will wake.
Damon allows himself to enter Elena's subconscious to say his goodbye, dancing with her and telling her that he'll never be ready to live the next 60 years of his life without her. Stefan and Damon move the coffin holding Elena to a crypt and have Bonnie seal the door magically to keep away those seeking the Cure. The season ends with the impression that quite a bit of time has passed.
Mystic Falls is desolate and run down after the return of the other Heretics, Lily's "family". The last scene shows Damon looking torn standing on the clock tower he once sat on with Elena. At the start of season 1, Damon was a self-proclaimed loner,  often keeps to himself.
Despite his initially antagonistic relationships with humans such as Alaric Saltzman and Sheriff Elizabeth Forbes, Caroline's mother. Damon gradually involved himself into the lives of many people in Mystic Falls by developing friendships with several humans. After spending time with Elena Gilbert, Damon becomes more empathetic and falls deeply, madly and passionately in love with her. He always puts her safety first before anyone else, even his.
Damon's most prominent love, aside from Elena, was Rose. He met her while searching for Klaus and hooked up with her shortly after. Unfortunately Damon ticked off Jules, a werewolf, and she showed up on a full moon for revenge. Damon has had a challenging relationship with his younger brother Stefan Salvatore for over a century. Before they became vampires, they both loved the vampire Katherine Pierce. Damon shows that he has nurtured a long-standing desire to reunite with Katherine throughout the first season. In the first season, we learn that it was Stefan who convinced Damon to feed and complete his transformation after Katherine turned both brothers into vampires.
Damon is always there for Stefan when it really matters, e. They both actually love each other but won't admit it, however: After learning of Katherine's deceit, Damon starts to fall for, Elena. In general, Damon is fiercely protective of Elena and always puts her safety ahead of all else. Damon comes to Elena's rescue at the Miss Mystic Falls pageant when Elena is left stranded without a partner, and the two dance.
In the episode "Rose", Damon confesses his love for her only to compel her to forget about it because he doesn't believe he is worthy of her. Throughout the third season his relationship with Elena grows; she learns to fully trust him, and they begin to rely on each other as a team. They share two passionate kisses, but Elena remains in denial about her feelings for him. After a long struggle, Elena still chooses Stefan much to Damon's dismay. In the following season, however, Elena realizes that her feelings for Damon cannot be denied any longer.
She and Stefan break up, and in the following episode Damon and Elena finally get together and have sex. Damon and Elena then both individually discover that Elena is sired to Damon, making Elena's feelings unfortunately known; however, Elena insists that her love for Damon is the most real thing that she's ever felt in her entire life.
In an interview before the season finale, Julie Plec stated that "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 diehard belief that she loved Damon, that she loved him more than she'd ever loved anyone. Damon and Elena spend the next few months together, having the summer of their lives. When Elena has to leave for college, Damon stays behind in Mystic Falls and they have a functional long distance relationship.
However, in the episode "Original Sin", Tessa, who is revealed to be Qetsiyah, tells Damon that the doppelgangers are fated to fall in love and that he is only a bump in the road that makes their story interesting. Damon refuses to believe in this and assures Elena that he will fight for her and their future together as she is his life.
It is later revealed that there is nothing fated about Stefan and Elena, but that they were merely drawn together by a spell. After a tumultuous, back and forth relationship, Damon and Elena get back together at the end of the season, and they choose to sacrifice themselves together to save Stefan and Alaric and their other friends on the Other Side.
Damon says his last goodbye to Elena, telling her that she is by far the best thing that has ever happened to him, and that being loved by her is "the epitome of a fulfilled life", as Elena sobs inconsolably. In season 6, Elena is unable to move on from Damon's death months later. She pretends to be happy, but she is secretly taking witch herbs to hallucinate Damon.
When the herbs make her dangerous to humans, Elena decides to have Alaric compel away her memories of Damon, because she will never be able to move on otherwise. When Damon returns, he attempts to help her remember their love story, but the compulsion will not break. Not remembering any of the good things about Damon, Elena still decides to give him another chance. She slowly falls in love with him again, ultimately declaring that no matter whether she has memories of him or not, she always finds her way back to him. When Bonnie returns from the prison world, she gifts Damon with the cure for vampirism, knowing that he wanted to give it to Elena.
However, Damon is afraid that this will mean losing Elena. They discuss what a human life together would be like. Elena initially rejects the cure, but Damon decides to take it with her so that they can have a human life together, including children. Damon always wanted Elena to have the human life she always dreamed of. Elena takes the cure, which breaks the compulsion, and her memories of Damon return to her. She recalls a memory from season 4, where Damon declares that there would be nothing more miserable than becoming human again.
Elena is afraid that Damon would regret taking the cure, so she challenges him to think it through carefully. Stefan attempts to convince Damon that becoming human would be a bad decision, but Damon ultimately realizes that one lifetime with Elena is infinitely better than an immortal one without her, and confidently believes her to be his soulmate. Damon and Elena excitedly anticipate the beginning of their human future together, until Kai puts Elena under a sleeping spell, tied to Bonnie's life. Damon spends the next two seasons devoted to Elena, waiting for her to wake up. He repeatedly states that he is miserable without her, and will spend the next 60 or so years unhappily until Bonnie dies.
However, Damon is committed to staying true to Elena, and doing right by her. Elena is shown to be Damon's moral compass, and his guiding force throughout the two seasons. The phoenix stone's influence remains, and Damon accidentally lights Elena's coffin on fire or so he thinks. Believing that he has unwittingly killed the love of his life, Damon becomes suicidal.
When confronted with the hunter Rayna, Damon commands her to kill him because he is already in hell in a world without Elena. Enzo then reveals to Damon that Elena is still alive, renewing Damon's hope. When Damon realizes that he is a potential danger to his friends and family because he does not believe he is good without Elena, he decides to desiccate himself next to her.
He write to Alaric that before Elena, he didn't know what it was like to be happy, fulfilled or complete, and that he doesn't want to continue living without that feeling. After Stefan wakes Damon from his desiccation, Damon continues to be devoted to his future with Elena. At the end of season 7, he is lured into a trap by a siren, hearing Elena's voice calling out to him.
When the siren takes control of Damon's mind in season 8, Damon spends a significant amount of time sleeping, seeking refuge in dreams of his memories of Elena. When Sybil erases Elena from Damon's consciousness only to insert herself into their memories, Damon fights back, instinctively drawn back to Elena. His love for her prevails, and he breaks the siren's mind control, regaining his memories of Elena.
Julie Plec stated that "I think the only hope that he's holding on to is the idea of the two of them living in Tribeca in their brownstone and raising kids and having a life together as humans when this is all said and done. They begin their life together, getting married while Elena goes to medical school and becomes a doctor. Eventually they return to Mystic Falls to grow old together, where they died together of old age. We last see them walking hand in hand in the afterlife before reuniting with their respective families. Alaric is a vampire hunter looking to avenge his wife by killing the vampire that killed her.
It is soon revealed that the vampire that Alaric is hunting is actually Damon. Before killing Alaric, he confesses that he didn't kill Isobel but turned her. Alaric is brought back to life by the Gilbert ring. The two remain enemies but work together on occasion. Eventually, the two become best friends and drinking buddies. Even after Alaric is turned into a vampire who kills other vampires, Damon does his best to ensure that they don't have to kill him. But with Elena's death, Alaric dies as well while Damon holds him.
In the episode, "Memorial", it's clear that Damon still misses his friend as he talks to Alaric at his grave. Unknown to him, Alaric listens to the whole thing and even responds with "I miss you too, buddy". They first interacted in Haunted, when Damon learned that Bonnie had come into possession of the Bennett Talisman. He needed this to open the tomb which Katherine was locked in for years or so he believed. At first, Bonnie didn't want to have anything to do with Damon, saving his life only for Elena's sake and soon blaming him for Caroline's transition into a vampire.
However, as time went on, Bonnie was put into situations where she had to work with Damon to achieve what they both wanted albeit reluctantly at first. Their teamwork has often proved to be beneficial for the both of them. Their relationship has even come to a point where Damon is visibly worried for Bonnie's well-being and was devastated when he found out about her death. The improvement of their relationship is seen in Damon's efforts to help bring Bonnie back from the dead.
However, their unique friendship hit a speed bump when Damon reverted to his old ways. Finally, they stood side by side with each other as The Other Side collapsed, holding each other's hand and at peace with what is to come for the both of them. They later discover that they are trapped in a Prison World.
During that time, they start to bond and form a close alliance to take down Kai. Before sending Damon back home, she mentions that he's not exactly the last person she would wanna be stuck with. When Damon returns home, he does everything he can to find a way to bring Bonnie back, including a long road trip to Oregon to seek the Gemini Coven, and also compelling Alaric to steal the Ascendant from Jo. It's shown that Damon and Bonnie genuinely care about each other and have made sacrifices for each other.
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