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.

We're not that desperate, Stefan. The guy tried to barbecue me!

Rose: It doesn't mean I can't be a special friend.
Damon: I think I like you.

Damon: You sure you can do that?
Rose: I don't love men that love other women. I think more of myself then that.

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

Dear Elena, yes you heard that correctly. Hell has frozen over. I'm writing it all down. Granted, I'm half a bottle in thanks to my 1950 Chateau Cheval Blanc, a bottle I waited 65 years to open. I used to spend nights sitting in my wine cellar convincing myself I could hear it age, tannins growing, fermenting, but appreciating its beauty didn't make time go by any faster. The bottle just laid there on its shelf, torturing me while I waited for Katherine and time stood still. Eventually I convinced myself that no sip of that wine could ever taste as good as I dreamt it would. And that is the story of why I drink bourbon. I don't know who I am without you, but I know that as long as I'm with you, time will stand still. So who is Damon Salvatore without Elena Gilbert? A selfish friend, a jealous brother, a horrible son? Or maybe with a little luck, I'll do right by you. Because you may be a thousand miles away or a hundred years away, but you're still here with me and my heart is right there in that coffin with you. Until you come back to me.

Damon