“I’ve been in love. It’s painfull, it’s pointless and overrated ” – Season 1, Episode 06
” No, I’m not upset. Upset is an emotion specific to those who care. ”
” You’re surprised that I thought you would kiss me back? You can’t imagine that I’d believe that you’d want to? That what we’ve been doing here means something? You’re the liar, Elena. There is something going on between the two of us, and you know it ”
” What I’m about to say is probably the most selfish thing that I’ve ever said in my life…. I just have to say it once. You just need to hear it. …I love you, Elena. And it’s because I love you that I can’t be selfish with you, why you can’t know this. I don’t deserve you, but my brother does…. God, I wish that you didn’t have to forget this, but you do. ” – Season 2, Episode 08
“What do you want to hear? That I care about Rose? That I’m upset? Well, I didn’t, and I’m not.”
“I feel, Elena. Okay, and it sucks. What sucks even more was that it was supposed to be me. Jules was coming after me.”
“I have a secret, a big one. But I’ve never said it out loud. What’s the point? It’s not gonna change anything. It’s not gonna make me good, make me adopt a puppy. I can’t be what other people want me to be. What she wants me to be. This is who I am.”
“You are my existential crisis. Do I kill you or do I not kill you? But I have to Jessica, because I’m not human. And I miss it. I miss it more than anything in the world. That is my secret. But there is only so much hurt a man can take.” – Season 2, Episode 12
“I’m in love with a woman I can never have.”
“The point is, I’m in love with her and it’s driving me crazy. I’m not in control.”
“I don’t trust myself around anyone, Andie. I’m bad, Andie. I do things. I kill people.” – Season 2, Episode 13
“Let me be clear about something. If it comes down to you and the witch again, I will gladly let Bonnie die. I will always choose you. ” – Season 2, Episode 18
“No, no. You know what? If I’m going to feel guilty about something, I’m going to feel guilty for this. [Damon kisses Elena] ” – Season 3, Episode 10
“[doing a Stefan impression]:
Dear diary, a chipmunk asked me my name today. I told him it was Joe. That lie will haunt me forever.” – Season 3, Episode 16
Damon: Still here.
Elena: We need to talk.
Damon: Stefan told me about the breakup. I’d say I’m sorry, but I’m not.
Elena: What did he say?
Damon: Oh, you know Stefan. The guy just went in and on about it, wouldn’t shut up.
Elena: So he didn’t tell you why?
Damon: Nope. But I’m sure it has something to do with you acting weird. So why don’t you tell me?
Elena: You.” – Season 4, Episode 7
“Elena: What’s that face?
Damon: What face?
Elena: That face.
Damon: I’m happy. ”
“Elena: Listen, Damon, we…
Damon: No, no,no,no, no. Don’t ruin it.
Elena: You don’t even know what I was gonna say.
Damon: Well, I’m assuming it starts with „What are we and ends with „going to tell Stefan?.
Elena: He should know.
Damon: I know he should know. I just don’t know when he should know it.
Elena: Well he knows that something’s going on between us. I mean, it’s the reason that he and I broke up.
Damon: Yeah, but can we just let ourselves enjoy one secret selfish day before we destroy his?
Elena: Maybe we shouldn’t…
Damon: No, Elena, this is our time. It’s never been right before and it is right now. Just one day. One day?
Elena: Okay, one day.”
“Stefan: It was your blood that turned her, right? She’s been different since day one because of you, you can’t deny that.
Damon: Sure I can. I finally got Elena to a good place about being a vampire. And you two idiots can’t stand that she’s happy because of me. ”
“Damon: Pfft. The sire bond’s not that literal, Stefan.
Stefan: Really? Name one thing that you’ve asked her to do that you haven’t gotten, huh?
Damon: You know what I haven’t gotten? Blame, guilt. I get it, Stefan. I get that you’re pissed that Elena dumped you because she has feelings for me. Bet you blame the sire bond for that too.
Stefan: Yeah, you know what? I absolutely do.
Damon: Why? Because it’s impossible that she could have feelings for me?
Stefan: No, because it’s impossible for her to be so blind that she doesn’t see how wrong you are for her.”
“Stefan: As much as I hate this sire bond, I shouldn’t take it out on you. It’s not really your fault. Damon: Well, don’t get all warm and fuzzy on me yet.”
“Stefan: So what are we gonna tell Elena? Damon: I was hoping we wouldn’t have to tell her anything.
Stefan: We can’t just lie to her.
Damon: It’s not a lie. It’s an omission for the greater good.
Stefan: Oh, I See. I see. That’s Damon-speak for. Let’s not do the right thing. Let’s just do what’s right for me.
Damon: Oh, what about you all selfless one? Are you doing what’s best for Elena or what’s best for you? Cause it looks to me that the only reason you wanna break Elena’s sire bond is to restore her original factory Team Stefan settings. I’m gonna go get a drink. Hunt me down when you stop being a dick.”
“Damon: Are you saying there’s no spell?
Nandi: The bond can’t be broken with magic. A vampire only bonds to her sire when she has feelings for him before she turns. Human feelings. Vampirism only heightens those emotions. You want her free? You have to set her free. Tell her to live her life without you and never think of you again. To stop caring about you. And then leave her. That’s the only way around the sire bond.”
“Stefan: Must’ve been hard doing the right thing especially when it’s not something you wanna do.
Damon: Get to the point, Stefan. You don’t think I’m gonna be able to do what I need to when I have to tell Elena to stay away from me.
Stefan: Well, I mean, selflessness isn’t exactly one of your most obvious character traits, Damon.
Damon: Yeah, well, one of these days you’re gonna realize you don’t know me half as well as you think.”
“Damon: You know what would make me happy? To know that this entire time that I’ve been completely in love with you that what you actually felt for me was real.
Elena: It is real. I know it is. Damon, I know what you’re about to do. Please, don’t do this to me.”
“I don’t wanna do this, Elena. I’m not the good guy, remember? I’m the selfish one. I take what I want, I do what I want. I lie to my brother, I fall in love with his girl. I don’t do the right thing. But I have to do the right thing by you. ” – Season 4, Episode 8
“Damon: Well, let’s just say I’ve been around a long time. I’ve learned a few things.
Elena: So Damon, tell me. What is it that I want?
Damon: You want a love that consumes you. You want passion and adventure and even a little danger.
Elena: So what do you want? – That’s my parents.
Damon: I want you to get everything you’re looking for. But right now, I want you to forget this happened. Can’t have people knowing I’m in town yet. Good night, Elena. ” – Season 3, Episode 22
[Damon kisses Elena]
“…Elena: What was that for ?
Damon: Because I’ve had a really crappy day, and I needed it…” – Season 4, Episode 21