Tessa: Buy you an I'm sorry drink?
Damon: More like an I'm sorry keg.

Guilt. Don't know it, but I've heard it can be a royal bitch.

Why do you suck so badly at killing yourself?

I don't speak crazy person Jer, you're gonna have to translate that for me.

You took one philosophy class and now you're the queen of nature versus nurture?

Stefan: Katherine took the Cure?
Damon: You have a lot to catch up on, Stefan.

Play nice. Or I'm gonna revisit the deep, dark well idea.

I know I said it doesn't bother me that you have a psychic connection to your ex-boyfriend, but I don't need the play by the play.

Silas: What I don't get is why she likes you.
Damon: That's because you haven't had sex with me.

Caroline: Damon. Towel. Knock!
Damon: Caroline. No one cares. No!

You do realize you are dating a reformed serial killer, right?

How is it even when you're dead you're the bane of my existence?

Vampire Diaries Quotes

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

The best revenge is patient, cultivated. Nobody sees it coming until it's too late.

Enzo