Need I remind you that Jeremy once had an affair with a ghost? The only thing that was missing was a sappy love song and a pottery wheel.

It's difficult to explain to your brother that you just broke up with the former love of his life and then broke the bed.

I killed him to convince myself that you were right, that I was the type of person who could kill in cold blood and I was never gonna change.

Damon: The second we're cured of this and don't wanna rip each other's heads off, I am gonna hunt you down and give you the most mind blowing night of your life.
Elena: I think I can schedule you in.

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

What's up, Doc?

Tyler: You're a joke, Damon.
Damon: Says the guy pining for the girl who slept with Klaus.

Bonnie: She would kill you.
Damon: Cool and then me and all her dopplegangers can start a baseball team on the other side.

Stefan: Come on Damon, you're better than this.
Damon: On the contrary brother, I'm better like this.

I happen to like my old sadistic self?

You are literally the best person I've ever known. And for me to think I could ever change you was giving me way too much credit and you way not enough… you're the good. And I need a little good in my life.

Enzo: Do you wanna kill him or should I?
Damon: I hate deadlines.

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.