Our life is one, big proverbial coin toss.

Have I told you lately how much I appreciate you not being the dumbest brother on Earth?

Damon: All this over one girl.
Stefan: She's a pretty special girl.
Damon: Yeah, she is.

How many dessicated hybrids does it take to screw in a light bulb?

I do stupid things, Bonnie... like let my friend die with dignity when I should have just killed him.

Damon: Sorry I killed you... twice.
Alaric: So I have to actually die to get a real apology out of you.

Sorry to spoil your seven minutes in heaven. We have a problem.

Don't be a dick. Listen to your sister.

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.

Didn't you find it weird that you made a friend so fast? Have you met you?

Dead vampire is redundant.

Next time we compel him, we need to make him better at baseball.

Vampire Diaries Quotes

There's no such thing as a bad idea. Only poorly executed awesome ones.

Damon

I do believe in killing the messenger. Know why? It sends a message.

Damon