Andie: So why can't you have her? She's with another man I assume.
Damon: Yeah, but that's not the point. The point it, I'm in love with her. It's driving me crazy. I'm out of control.

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?

Vampire Diaries Quotes

You want a love that consumes you. You want passion and adventure, and even a little danger... I want you to get everything you're looking for. But for right now, I want you to forget that this happened. Can't have people knowing I'm in town yet. Goodnight, Elena.

Damon

Damon: You know what they are? Children. Like lighting a candle's going to make everything OK, or even saying a prayer. Or pretending Elena's not going to end up just like the rest of us murdering vampires. Stupid, delusional, exasperating little children. And I know what you're going to say: 'It makes them feel better, Damon.' So what? For how long? A minute, a day? What difference does it make? Because in the end, when you lose somebody, every candle, every prayer is not going to make up for the fact that the only thing you have left is hole in your life where that somebody that you cared about used to be. And a rock with a birthday carved into it that I'm pretty sure is wrong. So thanks, friend. Thanks for leaving me here to babysit. Because I should be long gone by now. I didn't get the girl, remember? I'm just stuck here fighting my brother and taking care of the kids. You owe me big.
Alaric: I miss you too, buddy.