Enzo: You don't need pain to keep our connection alive. You are a witch, after all.
Bonnie: A witch who can't do magic.

I know this is a lot for you, Matty, but I miss my family. Don't worry, I won't get all weepy before the drinks arrive.

Kelly

Hi, I'm Katherine, the bitch that will destroy your lives for all eternity.

Damon

Caroline and Bonnie are probably already rehearsing. You don't want to seem unprepared.

Damon

Alright professor, how do we get rid of the Queen of Hell?

Damon

Hey, are you part of my Uber pool?

Uber customer

Damon: It's suicide, Stefan, and if you screw this up, we don't know what he'll do to Elena.
Stefan: I'm sorry Damon, but I have to do this.
Damon: I'm sorry, too, but I can't let anything happen to her, or you.

Enzo: Are you happy?
Bonnie: Right now? Yes, perfectly.
Enzo: Then why not forgive Stefan?
Bonnie: Do you really have to ask?

Damon: Sorry, Blondie, probably best if you don't know.
Caroline: Great, another Salvatore brother freezing me out.

Sorry, this place had the nearest holding cell.

Damon

Kai: Anything else?
Stefan: Damon.
Kai: Aww, that is so sweet, I'll be sure to tell him you were thinking of him when you died.

Yeah, well you get the idea. Crushed it, literal mic drop.

Kai

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.