Season FiveEdit

After spending the summer together with Damon, Elena prepares to leave for college, but has a feeling that something bad is about to happen. Damon told Elena she had to go to Whitmore, which is just a few hours away, and he'd take care of Jeremy. Elena opening the door again to give Damon a quick kiss. Elena leaves with CarolineSheriff Forbes drops them off at college, hugs Elena goodbye, and says thather father "fell in love with medicine" there. Caroline and Elena discover they have a roommate, Megan. Elena welcomes her, much to Caroline's chagrin. Caroline drinks Megan's protein water, hoping she'll upset Megan enough to leave, but discovers it's laced with vervain and revealing Megan knows about vampires. [1]Elena and Caroline at the party.Elena, Caroline, and Megan go to a party Jesse invited them to. Elena and Caroline haven't been invited in, however, so decide to go home early. Elena leaves a message on Megan's phone, only to receive a panicked phone call from her. Megan says she's being chased, and moments later her body falls next to them. Elena realizes a vampire killed her. Elena and Caroline learn that Megan's death is being ruled off as a suicide. When asked if they have seen Megan's phone (which Caroline took), they say no. Whilst going through Megan's pictures, Elena finds an image of Megan with Grayson. [2]Elena GilbertIn True Lies, Elena and Caroline are still wondering about mysterious death of their roommate Megan but they carry on living their new college life and attend their classes as freshmen. Elena signed them up for the class of Wes Maxfield. At the bonfire party, Elena was also able to gather information from Jesse when he gave her some details about Maxfield. Silas visited Elena a little visit at college and revealed what Damon has been hiding from her including Jeremy getting expelled from school. Elena obviously gets upset with Damon lying to her and Silas used that to control Elena to kill Damon. Elena got Damon tied up to a chair and ready for the kill but Damon figured out that Silas used his mind control power over Elena so he tried his best to make Elena resist the "rage" by thinking about her worries of Stefan. [3]Elena and Damon kiss passionatelyLater, 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. [4]Elena protecting KatherineIn Original Sin, Elena had a very strange dream in which she saw Stefan at a bar screaming. Damon, now getting a little annoyed at the connection between Elena and her ex, had no choice but to address things when Katherine walked in the room having had the exact same dream. This called for a road trip. Damon and Elena found the bar from her dream. They left a sleeping Katherine in the backseat while they compelled a bartender. The good news was the bartender remembered a freakish amount about what happened to Stefan. The bad news was that Nadiahad found her way to the bar, and she wanted Katherine. Elena distracted her long enough for Katherine to run, but Nadia was stronger than Elena. Before Elena could blink, or Damon could be helpful in any way, shape or form, Katherine and Nadia were both gone. Elena wanted to go after them and leave Damon to find Stefan, and 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. [5]Elena stops Katherine.Elena caught up with Katherine. Elena took the opportunity to explain that, unlike Katherine, she values her humanity and gave her the cure for the chance to find her own after having buried it under "500 years of bad behavior." But chat time ended quickly, when Nadia snapped at the necklace belonging to Elena. 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. He explained that they didn't have a chance because of the universe. "We're a lost cause no matter what we do," he told Elena. 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. [6]"I am with Damon."In For Whom the Bell Tolls, Elena along with Damon tries to make Stefan remember his past. She visits them at the Grill but Stefan can't remember her name which upsets her. She discusses with Damon about how to deal with him. Later they go to the cemetery Mystic Falls for the traditional Remembrance Day to honor the dead, Damon has to go and leaves Elena and Stefan alone, they talk about their family tragedies, he asks her how they met and Elena leads him to school to relive the moment. At the school, reliving the moment doesn't really make Stefan remember but Elena continues to try. She then takes him to the Wickery Bridge to show him how she became a vampire. They are having a good time until Stefan tries to kiss her and she stops him saying that she is with Damon. Stefan is hurt by this as both Damon and Elena didn't tell him the truth about them dating. He then disappears leaving Elena alone. [7]Damon consoles ElenaThen 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 to fix Stefan's memory and Damon finally tells her about Bonnie's death which shocks her. Later, Elena is freaking out as she can't find a dress for Bonnie's funeral and breaks down into tears telling Damon how she can't do this again. Damon hugs her affectionately and tries to calm her down. [8]Bonnie's funeralElena later along with Jeremy, Caroline, Damon, and Matt attend a funeral in Bonnie's honor. She scatters white feathers over the stump, then she backs out crying and Caroline hugs her. Then Bonnie through Jeremy talks to them from the Other Side. Bonnie tells Elena that she saw her happy and she wants her to go to college and continue to live a normal life. Elena continues to cry as Damon consoles her. [9]ElenaIn Monster's Ball, Elena has been avoiding talking to Damon on the phone. Instead, she's been sharing her exposition with her diary: "Dear Diary, do you ever get sick of me writing about death?" It's been four days since Bonnie's funeral, and Elena is back at school trying to move on by discovering what Maxfield, who covered up Megan's death, really knows. Damon popped up at the school to accept Elena's invitation to the Whitmore Historical Ball. It's the one time of year that the college's entire collection of artifacts is put on display and people dress up as historical figures.  Aaron was out on campus paying his respects to Megan, Elena and Caroline's dead roommate, at a sad makeshift memorial. He seemed to know her death wasn't a suicide and that Megan's flower of choice was sunflowers. [10]Delena danceHe wouldn't give Elena his name. Elena and Damon were dressed as Anne Boleyn and and Henry VIII. Damon wanted to dance but Elena wasn't in the mood. She said it's not her fault that Bonnie died but it is her fault that she didn't figure it out sooner. She's not gonna let Megan's death fall through the cracks, too. She talked to Aaron and compelled him to tell her whether he killed Megan (no) and why he's avoiding her -- because everyone around him dies. It's a curse, he said, and if she had any idea about survivor's guilt, she'd leave him alone. She compelled him to forget the conversation.

[11]Elena with Damon.

Dr. Maxfield was dressed as Dr. Jekyll. He wasn't responsible for the whereabouts of his darker half, Mr. Hyde, he joked to Elena. Then she danced with him. Maxfield told Elena his theory that a vampire hunted Megan down, ripped her throat out and threw her off the building. And then he said they were never going to see each other again because there are people at this school watching her and her friends and asking questions she doesn't want them to ask. He suggested she pack her things, drop out, and move back to Mystic Falls. Damon and Elena found Silas. Elena thought it was good that Silas is out of commission. But Damon knew it wasn't. Back at Salvatore Mansion, desiccated Silas was on the couch as Elena and Damon talked. The only way for Silas to trade his life for Bonnie's is if he's a witch. The only way to become a witch is to have the cure. Someone was knocking on the door and it turned out to be Katherine. Katherine thought she was there so they could show her that she'd eluded death yet again. They finally did something right for once. How did it feel? "Thrilling," Damon said. And she figured it out. Damon bit her neck and she begged him: She said Silas would need all of her blood and she didn't want to die.  "Goodbye, Katherine," he said, and he held her head down to Silas' mouth. Silas' hand came up to her head. Katherine dropped to the floor. But then Damon heard something. Her heartbeat. She awoke. "Am I in hell?" she asked.</span>

[12]Elena and Damon cuddling.In Handle with Care, when Damon and Elena are snuggling on the couch and having a sweet moment, Silas comes in ruins their blissful moment to discuss their plans for his death. Elena is having trouble trusting Silas’ word that he will bring Bonnie back before he departs the mortal world for good, so he snarkily offers to pinky swear. Everyone is looking for the anchor now. Silas wants to die and find peace. Silas then refuses to allow Elena to come along when she looks like his true love and doesn't want to stare at her all day. As Elena gets annoyed, Silas uses his magic to shoot the crossbow at Elena's leg. This upsets Damon and he hurries to help her.

[13]Elena trapped with Tessa & StefanLater,Elena calls Stefan's phone, which Qetsiyah answers. She implies that she and Stefan slept together, luring Elena into the cabin. Once there, she uses Stefan's phone to call Damon and threatens to kill Elena if he doesn't kill Silas. Stefan tells Elena that he wouldn't let to Qetsiyah hurt her. When Qetsiyah is distracted, Stefan stabs her and he escapes with Elena. Elena is grateful to Stefan for having protected her, as he always does and then says goodbye to him. Elena then joins Damon and Jeremy who are throwing a pity party for themselves due to their failure to bring Bonnie back. They let Elena in on the big twist for the episode though, and Damon introduces Elena to Amara. [14]Elena showing offIn Death and the Maiden, Elena told Stefan how she lost a friend when he lost his memory, so she wanted to start over. But that didn't exactly work for Stefan, considering he could suddenly remember everything.After learning Stefan's plan, Elena was worried that Stefan would get himself killed by going after Silas. But if Stefan didn't get to kill him, Silas would win. Stefan told her about moments of stillness in the safe. Every time he closed his eyes now, he relived those three months, and if he didn't kill Silas and make it stop, he'd lose his mind or flip his switch... or both.

Elena was used in a spell, to transfer Amara from being the anchor to The Other Side to Bonnie being the new anchor and Qetsiyah had to have doppelganger blood to do the spell. Amara, Katherine, Elena, and Tessa all stood around Bonnie's grimoire (a talisman) as Tessa cut their palms and started chanting. But then Silas showed up and knocked the power out. Elena, as if she had just overheard Stefan's thoughts, told Damon to go find Stefan because he wasn't thinking right. Silas might have put him in that safe, "but we were the ones who were supposed to get him out of it." [15]Elena & Caroline unite with BonnieTessa was able to perform the spell in time and bring Bonnie back to life. Elena and Carloine were reunited with Bonnie. Later, Elena asked Stefan if killing Silas worked and if he is now OK. Stefan doesn't respond but rather asks her why is this all so important to her. She told him the truth that while he was drowning she was happy, she got everything she wanted, she got to be in love and had the summer of her dreams, she even got Bonnie back and she needs to know that he is going to be okay too. Stefan then admitted that he wanted it to be Damon and Elena to get him out of that safe. [16]Elena & CarolineIn Dead Man on Campus, Elena and Caroline plan Bonnie a blow-out "welcome back from the dead" party. Elena calls Damon to come to her party, but pauses to hand Aaron a flyer inviting him. She accidentally mentions something she compelled out of him before and has to do it again, but makes him agree to come to the party.Damon teases her about Aaron and then agrees to go to the party tonight.At the dorm, Caroline and Elena are getting ready for the party when Caroline gets a call from Jesse. They learn that Jesse has now become a vampire and decides to help him. [17]Elena bonds with AaronAt the party Elena and Caroline are keeping an eye on things and Elena tells her that Damon is with Wes making him questions about his experiments but Caroline is pretty sure that means Damon is going to kill him. Aaron arrives at the party and bonds with Elena over Jell-o shots and stories of how their parents died. He got passed around among relatives until he ended up with Maxfield. Elena calls Damon and he tells Elena about Jesse feeding on vampires, and she makes him promise not to kill Maxfield. [18]Elena saves DamonLater, Elena arrives at the laboratory of Professor Maxfield and finds Jesse feeding on Damon. Damon tells her that Jesse is going to kill him and so she grabs a shard of the broken door and stakes Jesse, killing him, just as Caroline runs up in time to see it. Elena feels awful, but Damon tells Caroline she had no choice and leaves to deal with Maxfield. Caroline and Elena are cleaning up after the party. Elena apologizes but Caroline is still upset as she doesn't trust Damon. She tells Elena that when she stops telling her how she really feels is when they will no longer be best friends. [19]Elena and AaronIn The Cell, Elena drops in on Aaron, who is reeling over the death of his roommate, Jesse. Even though Elena killed him, she pretends to be shocked. Aaron is overwhelmed by the fact that someone else close to him died.She asks about Wes, who became his legal guardian after his aunt Sarah died. She tells Aaron that Damon went to talk to Wes last night and no one has seen either of them since. She asks for his help finding Wes. Aaron thinks he knows a place. He takes Elena to the Whitmore House. He confesses that he owns the house as part of the Whitmore Trust he inherited when his parents died. His name's Aaron Whitmore. Elena looks at a picture and recognizes her father. Wes joins them, and says Grayson Gilbert was one of the best doctors the Augustine Society ever had. He then injects Elena with vervain. [20]Damon comforts ElenaElena wakes up in a cell next to Damon. Damon confesses he's been there before and tells her about Whitmore's torture, including cutting up pieces of them every day. He was there for about five years. He made a friend, Enzo, a soldier in Europe during WWII, who was also a vampire. Elena tells Damon that her dad worked with Whitmore and was an Augustine. She doesn't want to believe he'd be part of a place that would cut Damon's eyes out and breaks down. Damon confronts her and promises her that he'll get her out of there. [21]Elena learns of Damon's past.Elena thinks Stefan will figure it out and come rescue them, but Damon never told him he was locked up. Elena wants to know how he escaped, but Damon is not forthcoming with the details, saying only that it wasn't pretty. Elena convinces him to tell her by saying that she loves him and doesn't care what he did to escape. Damon finally tells Elena his shameful secret: he left Enzo to die during his escape. After massacring the party on New Years Eve and knocking over a candle, he tried to break the cage to free Enzo but the bars were laced with vervain and he couldn't get him out. Damon flipped his humanity switch so he would stop caring about Enzo, and left him to die in the ensuing fire. Elena was horrified that Damon left Enzo. [22]Elena and EnzoAaron comes down to the cells in the basement with his gun. He accuses Elena of killing Megan and possibly of killing his parents. Damon stops him, and says it was him. Damon explains that with Enzo dead, he had to carry out his revenge plan himself. He planned to kill all the Whitmores in a generation, except one, then let him grow up and start a family, and then kill all of them except one, and so on. And he did. Elena is disgusted and asks when the last one was. A few months ago, Sarah in Charleston. It was a weekend trip. Elena realizes they were together then. Aaron shoots Damon leaving Elena upset. Later, Elena wakes up strapped to an exam table next to another vampire. He introduces himself, "My name is Enzo." [23]Wes and ElenaIn Fifty Shades of Grayson, Elena wakes up on the surgical table in a familiar lab. Dr. Maxfield knocks her out to begin blood dialysis. Elena struggles to get free as Maxfield asks her how she justifies Damon systematically killing off members of Aaron's family tree. He justifies his torture in the name of science. He reads to her from a journal about electrocuting a vampire to see how much he could take. She's horrified, then he tells her its her father's journal. Everything Maxfield is doing, he learned from her dad. Elena realizes shes in her dads old clinic, which is now burned out from when the town tried to kill a bunch of vampires. Elena remembers following a soccer ball down the stairs when she was a child and seeing her dad's files and hearing the sounds of electricity. [24]Stefan saves ElenaElena remembers going down her dads clinic and hearing thrashing and screaming behind a door. Her dad found her and tells her everything is fine and today is a good day because he is going to save a little girl's life. In the burned out clinic, Wes is pleased to see her sample cells mutated with his compound. He plans to condition her to crave vampire blood, like he did with Jesse. She begs him not to turn her into a ripper. He jabs the needle into her chest and she hears Stefan's voice. She bashes Wes in the head and knocks him out and the needle falls from her chest. Stefan comes down and frees her. She grabs her dad's journal on the way out. [25]Elena crying after Damon's confessionBack at the house, Damon finds Elena reading through her dads journal. She found a reference to Megan in her dads 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 Elena is able to find the one positive thing out of all the torture in the journal. 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, Elena is trying to deal with her break up. She doesn't want to get out of her bed. Caroline and Bonnie bring Elena a "break up breakfast." Caroline does not even try to pretend she's not happy about the break-up, she even memorized what Damon said to her while Bonnie questions Elena as to why she is giving up. They are interrupted by Stefan's call who informs them about Katherine's terrible condition. [26]Everybody toast to Katherine's impending deathElena, Caroline and Bonnie arrive at the Salvatore house and join the drinking game of toasting to all of Katherine's bad deeds with Damon, Matt and Jeremy. Stefan comes downstairs to tell everyone they're being insensitive, but Damon warns him not to let the fact she's an Elena lookalike could the fact she's a manipulative psycho. Stefan mentions her seducing both him and Damon, turning them into vampires and starting a war with the town that got them killed. But he goes on to say that before that she was just a frightened girl shunned by her family, and she became a survivor, so that's what he'll drink to. Damon mocks Stefan for being so easy on her after one night of passion. Elena who doesn't know about this is evidently shocked. Their moment is interrupted by Nadia who explains she has found a way to save her mother. Damon forbids anyone to help, which Nadia expected, which is why she buried Matt in the safe somewhere on the property, without his ring. Elena and Stefan then willingly volunteer to save Matt's life. [27]Elena and Stefan are stuck with the TravellersStefan and Elena arrive with Nadia to a old house, she tells them that is looking for a Traveller for do a spell where Katherine take her body. Within in the house, is revealed that Elena and Stefan are needed to perform the spell for their doppelganger's blood, they are surrounded by many Travellers that begin to perform the spell, they are stuck unable to leave because their rings of light stopped working. Elena apologizes to Stefan for judging him. They are huddled in a corner to escape the sun's rays streaming through the dilapidated house. Stefan tells her that she should not to give up on Damon. After the Travellers have completely filled a pot each with their blood, their wounds begin to heal and they are released. [28]Katherine in Elena's body.Later, Elena visits Katherine on her death bed. Elena forgives her. “You weren’t born evil. You lost everyone way too young and didn’t have a family to look after you. Sound familiar?” Elena wanted to get out that “I forgive you” part before Katherine actually died so she didn’t lose that part of herself. Katherine wants Elena to give her the final sedative injection - “If anyone is going to inject me, it should be you.” She also does something very uncharacteristic: she thanks Elena for her forgiveness. But this is Katherine we are talking about, so as Elena injects her, she grabs her and says the traveler’s incantation. Both girls close their eyes, and “Elena” wakes to a phone ringing. Mia is on the other end, and she says some key word to activate Katherine. Nadia comes on the line and checks that it is Katherine. “Of course. I'm Katherine Pierce. I survive.” The episode ends with Katherine impersonating Elena. [29]Elena regains control.In The Devil Inside, Elena is possessed by Katherine and is fighting to get her body back. She breaks through as she is trapped by Nadia, but she pushes her back. She breaks through once more as Mia is casting a spell to give her body permanently for Katherine, a spell which would apparently destroy Elena's soul in the process. She hurts Mia and Nadia and runs off as she tries to stop them. She tries to call for help but Katherine has changed her password.  [30]Elena's last moment with Damon.She tries to run but Katherine works her way into her head as she runs. Elena reaches the edge of the party and runs into Damon's arms. She gets as far as "Damon, thank god," then Mia announces it's done. Elena's eyes gloss over black again and she seems to be Katherine again. Now fully in control of Elena's body, Katherine breaks up with Damon so now Damon thinks that they are over. Katherine also plans to take over her life as she knows that as long as she seems to be Elena, she is safe there, because everyone in this town always protect Elena. [31]Elena was absent in Total Eclipse of the Heart. She is referred to quite often as people are fooled by Katherine's imitation, however Elena was only shown in pictures with Damon on her cell phone from the previous summer which Katherine deleted and replaced her home-screen wallpaper with an image of Stefan and Elena.  [32]Elena greets DamonElena returns in Gone Girl after being absent for two episodes. After Katherine is daggered by the Traveler's Knife she dies for good and Elena gets her body back. Elena wakes up and greets Damon with a smile. She is happy to be back and assures Damon and Stefan that its her. However, it is revealed that Katherine injected her body with an enhanced Ripper Virus created by Wes turning Elena into a vampire ripper just like Damon. [33]Damon and Elena flirt on the phone.In While You Were Sleeping, Elena is informed by Stefan of her current augustine 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 is 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 wants 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. [34]Elena tries to feed on Stefan.On the phone, Elena realizes she's probably flunking her classes, and adds that to the list of things she needs to fix, including talking to Aaron Whitmore. The last time she saw him he had just learned she was a vampire and thought she wanted to kill him. Damon hems and haws and doesn't confess to killing him, only saying he doesn't think she'll find him. Elena gets off the phone when Stefan arrives with a new cell phone for her, and 4 oz. of his blood. She's woozy and starving and drains it. She asks for more, insisting she's fine. Stefan bites his wrist and shows it to her and she quickly loses control and charges him, but is trapped by the spell. ""You're not fine, Elena,"" he says. Elena realizes Katherine has turned her into a ripper. She's angry at herself for forgiving Katherine on her supposed death bed. Elena asks Stefan why Katherine stayed in town, and he confesses that Katherine was trying to get with him. He tells Elena they kissed, but he stopped it and realized what was going on. Elena then reads Katherine's entries in her journal and starts hallucinating Katherine and Stefan in the motel. She is angry because Stefan didn't realize that it wasn't her. [35]Elena meets Luke.She then calls Damon again and ask him to distract her. He mischievously asks what she's 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 is snaps out of her hallucination when a guy named Luke comes back early from spring break. She met him at the Bitter Ball as Katherine, but of course doesn't remember him. He thinks she's drunk. She tells him she's just starving. She compels him, feeds him her blood and is about to kill him to turn him when she notices bite marks on his neck and realizes Katherine must have been feeding on him. She stops and compels him to go get Bonnie. 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. [36]Damon tries to help Elena.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. [37]Damon and Elena decide to end their relationship.Back at the Salvatore Mansion, Damon offers Elena a drink to which she declines and then goes says how Damon should have noticed that it was Katherine not Elena. If he had, Aaron would still be alive, there'd be no virus. Damon points out she's blaming Katherine for his mistakes and making excuses for him. Damon says he killed Aaron because she broke his heart and this is how much control she has over him while Elena says that even after all this she is still here and this is how much control he has over her. [38]Damon and Elena have break up sex.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. [39]Elena & Damon's awkward morning.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. Meanwhile, Elena calls Bonnie from school. She tells her about breaking up with Damon and then sleeping with him. They realize that neither of them knows where Jeremy was last night. Elena sits down to talk to Jeremy's guidance counselor and finds she's not his primary contact but Damon is. Damon joins them. [40]Elena and Damon at Jeremy's PTM.Waiting for the teacher at school, Damon flirts with Elena whom 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. [41]Later at the 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. [42]Damon lets Elena go.At the Salvatore house, Jeremy tells Elena and Damon that he has decided to live with Matt and Tyler leaving both of them upset. Later, Elena is packing her stuff and Damon asks her to not leave but she says that when they are together they do bad things for each other and she can't live with that. Damon offers to drive her to Whitmore but Elena confesses that if he does that then she won't be able to control herself around him and thus they are gonna end up back here. Damon then slowly walks up to Elena, then she believes he is going to kiss her. Instead, Damon then shushes her and does the selfless/right thing, he takes his hands around her neck then slowly kisses her forehead and tells her Travel safe. Elena then seems shocked by Damon's act of selflessness as he walks away, she then seems upset that he finally let her go.

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