Similar to how both Stefan and Damon were in love with Katherine, they later both fell in love with Elena. Unlike Katherine, she did not enjoy both of their love for her. She initially dated Stefan and had a rocky relationship with Damon as she was nervous, assuming he was a killer. Over time, she became Damon's first friend and began to bring out his emotions. Elena and Damon grew closer when Stefan fell into Klaus's clutches and she eventually fell in love with him, too. However, she chose Stefan. Following her transformation into a vampire, she remembered the memories Damon made her forget and grew tired of Stefan's desire to "fix" her instead of accepting her. Enjoying how Damon made her feel alive, her relationship with Stefan ended and she began a relationship with Damon. Damon doubted her feelings for him when it was discovered she was sired to him so had to please him. After Elena lost her humanity, she taunted Damon, threatening to go back to Stefan since the sire bond was gone. However, after she regained her emotions, she confessed her love for Damon, choosing him.
Stefan returned to town to meet Elena after saving her from a car crash several months ago. Damon returns shortly after to free Katherine. However, a connection forms between Damon and Elena. After Damon discovers Katherine doesn't care about him and never loved him, he began to develop feelings for Elena. When Stefan loses control of his bloodlust, Damon and Elena bond as Stefan recovers. When Isobel demands a meeting with Elena, a recovered Stefan becomes suspicious when Damon seems to be acting like he's in love with Elena. Isobel later tells Elena that Damon is in love with her. Damon begins to become more open about his feelings and tries to become a better man so she can be happier.
After learning that Katherine always loved Stefan, not him, Damon forces himself on Elena despite her pleas that she only loves Stefan, and in a drunken rage he kills Jeremy. Stefan supported her choice to turn her back on Damon following this and kissed Stefan in front of him. Elena then played Damon. Eventually, they returned to an unsteady friendship and after spending a day with Elena, Damon confessed to Andie that he wanted to be the bigger man for her, but also wanted to be himself. He began an affair with Andie to take his mind off Elena. Both Stefan and Damon offered to be sacrificed in Klaus's ritual to save Elena's aunt, Jenna, and save Elena from more heartbreak. Klaus refused them both as Damon had a werewolf bite and he wanted to recruit Stefan. Elena kissed Damon on his supposed deathbed, officially forgiving him from regularly breaking her heart. They learned from Katherine that Klaus had taken Stefan away.
Damon decided to help Elena win Stefan back. He got her to confess her feelings for him first, however, and told her to remember how she felt when Stefan does return. Stefan continuously tries to kill Elena but she begins to rely on Damon and is shocked when he's not there to save her, however, he promises to never leave her again. Despite telling Elena he no longer loved her, Stefan later confesses that he's never stopped loving her and wants to win her back. Damon kisses Elena, telling her he has nothing to feel guilty about, and she tells Stefan who punches Damon. At a ball, Elena dances with both Damon and Stefan and, knowing Damon wants to protect her, gets Stefan to snap his neck so she can talk to Esther. He then says he's mad at her because he loves her, which she calls the problem, prompting him to sleep with Rebekah. Elena later kisses Damon, resulting in them fighting. Rose then talks to Jeremy about how Damon's either the best thing for Elena, or the worst. Stefan later kisses Elena and tells her they'll talk later. Elena later calls Damon after hearing that Klaus died, and tells him that she's choosing Stefan to say goodbye to, both because she loves him and he's closer to Caroline and Tyler.
Following Elena's transformation into a vampire, she resumes a relationship with Stefan, at the time time growing closer to Damon. When she has troubles drinking blood, she calls Damon and he supports her in her newfound vampirism. He pushes her to embrace her new lifestyle while Stefan becomes determined to "fix" her and make her human again. Stefan realises Elena is in love with Damon and breaks up with her. Elena then moves in with Damon to avoid Jeremy and admits she's upset that no one wants to accept her for who she is now instead of who she was. Damon then says he's never seen her more alive and they sleep together, beginning a relationship. When Caroline informs Stefan of this, he's distraught. Rebekah later compels Stefan, Caroline, and Elena to tell the truth. Elena confesses she still loves Stefan but no longer is in love with him and is in love with Damon. Stefan and Caroline realise that her feelings may have something to do with the fact that she's sired to Damon. Damon struggles to come to terms with this and begins to doubt her feelings for him. She later tells him that her love for him is the most real thing she's ever felt. Elena later becomes friends with Stefan and begs Damon to become human with her, but he refuses her. When Jeremy dies, Damon tells Elena to turn her emotions off, breaking the sire bond but also destroying all the love she had for him. Stefan tried to seduce her, but she made him care more than she did. She later tortured herself to prove Damon and Stefan wrong that they could make her afraid, and she teased Damon, saying she would go back to Stefan since the sire bond was over. Damon had killed Matt, which got her emotions back. Stefan confessed to Lexi that Elena was the love of his life and possibly "the one" but she confessed her love for Damon and it was real, choosing him. Stefan then told Damon that he was happy for him.
- Elena: "Just say it."
- Matt: "I just don’t get it. Your thing with them."
- Elena: "I know it doesn't make sense, but at the beginning, after my parents died, there was something about being with Stefan that just felt safe."
- Matt: "Safe? Elena, he’s a vampire."
- Elena: "I know, believe me, just saying it out loud it sounds crazy, but it’s like I knew that he would never stop loving me. Like he would never…"
- Matt: "What?"
- Elena: "Die. Like he would never die."
- Matt: "Like your parents did. And Damon?"
- Elena: "Damon just sort of snuck up on me. He got under my skin and no matter what I do I just – I can’t shake him."
- Matt: "Once you fall in love with someone, I don’t know if you can ever shake them."
- -- 1912
- Rose: "They had a fight. I know you want to stop it. Protect her from him. But you’re young, you don’t see what I see. It’s not just that she makes him a better person, she does, but he changes her too. Damon challenges her, surprises her, he makes her question her life, beliefs. Stefan is different, his love is pure, he’ll always be good for her. Damon is either the best thing for her or the worst."
- -- Heart Of Darkness
- Matt: "So, Stefan?"
- Elena: "He saved my life, you know. I never told you that. The night that my parents’ car went off the bridge, Stefan was the one that saved me."
- Matt: "So, do you feel like you owe him or something?"
- Elena: "No, it’s not that. It’s – after the accident, I kind of felt like I didn't know how to live anymore, like I didn't want to, but then being with Stefan… it just… somehow I figured it out. And that’s what love should be. You should love the person that makes you glad that you’re alive."
- Matt: "So then, what’s the problem?"
- Elena: "The problem’s Damon. When I’m with him, he just consumes me. And I know that I can’t love them both, I know that it’s wrong, but when I choose one then I’ll lose the other. And I don’t want to lose anyone else. I – I just – I wish that I had my mom here to give me some advice."
- -- The Departed
- Elena: "Matt’s taking me home."
- Damon: "To Stefan..."
- Elena: "Not just to Stefan, Damon. To Tyler... to Caroline."
- Damon: "Ah, I know, I get it. So, since I’m possibly a dead man, can I ask you a question?"
- Elena: "Yeah, of course."
- Damon: "If it was just down to him and me, and you had to make a choice, who got the goodbye, who would it be?"
- Elena: "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-I never unfell for him."
- Damon: "Yeah, I get it. Stefan, it’s always gonna be Stefan."
- Elena: "I can’t think about always. All I can think about is right now. And I care about you, Damon, which is why I have to let you go. I mean, maybe if you and I had met first..."
- Damon: "Yeah, maybe..."
- Elena: "You’re gonna be fine. You hear me? You’re gonna be okay and I’m gonna see you soon."
- Damon: "Real soon. Goodbye, Elena."
- -- The Departed
- Damon: "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. But for right now, I want you to forget that this happened. Can't have people knowing I'm in town yet. Goodnight, Elena."
- -- The Departed
- Stefan: "I love you, so much..."
- Elena: "Do wanna know why I was even on that bridge? I was coming back for you, Stefan. I had to choose... I picked you. Because I love you. No matter what happens, it's the best choice I ever made. God, sucks that I can't see you right now."
- Stefan: "I'm smiling."
- Elena: "Me too."
- -- Growing Pains
- Elena: "Stefan, why did you send Damon to come look for me instead of you?"
- Stefan: "I sent him because lately it seems like he’s able to get through to you in ways that I can’t. You’ll listen to him. You trust him, even when you can’t trust me."
- Elena: "I didn't mean to not…"
- Stefan: "Come on, Elena, I mean after everything that we've been through… You can admit it."
- Elena: "You've been so strong for me. Helping me, fighting for that girl that chose you, the girl that I was when I died on the bridge, and I love you so much for wanting to find this cure. Because I’d like nothing more than to get her back, because the – the girl that she’s become, that – that I've become is different, somehow. Darker. Who I am, what I want…"
- Stefan: "What you want, or... who you want?"
- Elena: "Something’s changed, between Damon and me. Much more than it ever used to be. It’s like everything that I felt for him before I was a vampire…"
- Stefan: "Has been magnified. Your feelings for him have been magnified."
- Elena: "I’m sorry. I don’t want to lie to you."
- Stefan: "You know, before when I was the, uh, the Ripper, I understood why you cared for him. I mean, I practically drove you to it. But now... I can’t do this, Elena. Not anymore."
- Elena: "I know."
- -- We All Go A Little Mad Sometimes
- Damon: "I wanted to apologize."
- Elena: "Good."
- Damon: "Let me finish. I said I wanted to. And then I realized, I'm not sorry."
- Elena: "You would rather die than be human, and you expect me to be okay with that?"
- Damon: "I didn't say you were supposed to be okay with it, I just said I'm not sorry. But you know what I really am? Selfish, because I make bad choices that hurt you. Yes, I would rather have died than be human. I'd rather die right now than spend a handful of years with you, only to lose you when I'm too old and sick and miserable and you're still you. I'd rather die right now than spend my last final years remembering how good I had it and how happy I was, because that's who I am, Elena, and I'm not gonna change. And there's no apology in the world that encompasses all the reasons that I'm wrong for you."
- Elena: "Fine, then I'm not sorry either. I'm not sorry that I met you. I'm not sorry that knowing you has made me question everything, that in death you're the one that made me feel most alive. You've been a terrible person, you've made all the wrong choices, and of all the choices that I've made this will prove to be the worst one. But I am not sorry that I'm in love with you. I love you, Damon. I love you."
- -- Graduation
- Stefan and Damon (Also known as the Salvatore Brothers, the Salvatores, and Defan)
- Elena and Damon (Also known as Delena)
- Elena and Stefan (Also known as Stelena)