Our life is one, big proverbial coin toss.

Damon

Alaric: Dr. Jekyll and Mr. Hyde?
Elena: What? Damon. He thinks he's hilarious.

You're dead, dude. Get over it.

Damon

Elena: You're the one who told me I can handle things on my own now.
Alaric: I meant like frozen dinners and SATs.

I didn't compel you in Atlanta because we were having fun. I wanted it to be real. I'm trusting you. Don't make me regret it.

Damon

Sage: Please don't tell me that you and Rebekah are friends.
Damon: Not unless you count hate sex.

Ric, the world can't stop just because you're an accidental serial killer.

Damon

Stefan smiles. Alert the media!

Damon

Damon: You have no sense of humor.
Stefan: I have no sense of Damon humor.

Today has been a no-good, very-bad day.

Damon

Katherine: Bad day.
Damon: Bad century.

I get it. He's the reason you live. His love lifts you up where you belong.

Damon

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.