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

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

Put the damn crossbow down, Pocahontas.

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

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

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

You want Doppleganger blood?!? I've got Dopplegangers coming out of my ears!

Hang on. I only count two doppelgangers. Where's Crazy Pants?

Damon: So, sex dreams about my brother.
Elena: That’s one way to change the subject.
Damon: Well, figured I’d skip the uncomfortable parts.

Liv has a twin? Is it possible for there to just be one of someone around here?

Listen, how I got this amazing body has nothing to do with science.

Katherine: I'm the one who taught you how to love.
Damon: I'll see you in Hell, Katherine.

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.