Elena: We have a situation.
Damon: Of the Doppleganger variety.

Elena, meet Crazy Pants. Crazy Pants, meet Elena.

It's called being secure. I can tell you believe in that by the way you wear your hair.

Put the damn crossbow down, Pocahontas.

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.

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.