Damon: I'm in love with a woman I can never have.
Andie: I knew it. I know how to pick them.

Andie: I can't believe you called me. I thought I was being way to forward when I had Jenna give you my number.
Damon: I like a woman who knows what she wants.

Damon: You need to stop doing that.
Elena: Doing what?
Damon: Assuming that I'll play the good guy because it's you who's asking.

Damon: You need to stop doing that. Elena: Doing what?
Damon: Assuming that I'll play the good guy because it's you who's asking.

Andie: What do you want, Mr. Tall, Dark and Handsome?
Damon: I'm not that tall.

Since Stefan got here earlier, I'll let him try it his way before I try it my way, which is a lot bloodier.

He's a werefolf. He needs to die. I'm willing to do it. It's a win-win.

I'm steering clear of all women at the moment... trust me, it's in the best interests of women everywhere.

John: You guys are drinking vervain.
Damon: It's an acquired taste.

Elena: We just need answers. Try not to do anything stupid.
Damon: Yeah, but stupid's so much more fun.

I'm a good guy now, remember?

Better watch your back. Because I might need to get a hero hairdo of my own and steal your thunder.

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.