Damon: We're never getting Elena back, yo uknow that, don't you?
Elena: Then we'll have to let him go.

I'd offer you a drink, but Katherine tells me you're more of a vampire-on-the-rocks kind of guy.

Damon: Do you trust me?
Elena: Yes.

Damon: It's very Katherine of you.
Elena: Not the way to make me feel better about myself.
Damon: It was a compliment. Sort of.

Damon: I am forming a secret contingency plan.
Elena: What is it?
Damon: If I told you, it wouldn't a secret.

I went behind your back. I freed Stefan. And you know what? It backfired. He’s an even bigger dick than ever. It’s just, now, he’s a dick that’s on our side.

Stefan: It’s precision born out of tragic boredom.
Damon: All that effort wasted trying to tell you how boring you were and you finally agree with me?

Careful, Stefan, your manhood is showing.

Stefan: What's the point of the jailbreak?
Damon: I thought you needed a hug, Stefan

I happen to like the edge, Stefan. Your problem is your inability to resist falling over it.

Elena: How does he look?
Damon: Pasty and pouty.
Elena: He'll have to get over it.

You’re right. I didn’t have to kill you. I do a lot of things I don’t have to do.

Vampire Diaries Quotes

Oooh, you know I don't know. Every time we try and go on a date you get kidnapped, I get sent to a prison world, or your feelings get compelled away...

Damon

Damon: My new girlfriend. Andie Starr. Action News.
Alaric: It's not called Action News.
Damon: I know. I like just saying it.