Damon: What the hell’s wrong with you? You’re not supposed to witchy migraine me.
Bonnie: You’re not supposed to kill Tyler.

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.

Vampire Diaries Quotes

Elena: Why don't you ever let anyone see the good in you?
Damon: When people see good they expect good. And I don't wanna live up to anyone's expectations.

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.

Damon