She's Katherine. She loves to play games.

Damon

He kissed Katherine, not me. I wouldn't do that.

Elena [to Stefan]

Katherine wants you dead, there's zero you can do about it. You will be dead.

Damon

Damon: Somewhere along the way, you decided I was worth saving. I wanted to thank you for that.
Elena: You're welcome.

Damon: I'm not a hero, Elena. I don't do good. It's not in me.
Elena: Maybe it is.

You saw what I was able to do tonight. I know who I am now. If Damon spills one drop of human blood, I'll take him down.

Bonnie

Life sucks either way, Jeremy. At least if you're a vampire, you don't have to feel bad about it if you don't want to.

Damon

Even I can't remember why, I still feel empty, alone. Making me forget won't fix it.

Jeremy

Stefan: I try so hard to hate him, I guess it's just pointless.
Elena: You care about him, so do I. But I love, Stefan.

Elena: I'm asking you not to.
John: That doesn't mean anything to me.
Elena: As my father, it should.

Tyler: I said I was sorry.
Caroline: You made out with his mother and then you beat him to a pulp. You're gonna have to do a little better than "I'm sorry."

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

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