Damon: Just between us bad guys, has anyone ever earned their way out?
Cade: I wouldn't want to give you false hope.

Bonnie, I've failed you in so many ways as a mother, but I will not let you destroy yourself.

Abby

The clock is ticking on Stefan's life, but, by all means, give Matt a physical.

Damon

I need to borrow a book. Maxwell family tell-all. Guess it's been out of print for a while.

Damon

Caroline: What is all this?
Stefan: That's me.
Caroline: No, this is Cade. He made you do this.

Matt: Everything okay?
Alaric: No, it's bad.

Damon: I'll deal with Stefan.
Bonnie: I already did.
Damon: What do you mean?
Bonnie: He's human now.

Caroline: I feel like Mystic Falls just isn't as safe as it used to be.
Matt: Tell me about it. Is that ancient tupperware?
Caroline: [laughs] Elena, Bonnie and I made our own time capsule when we were eleven. Buried it right under this tree and I cannot believe it is still here.

Stefan: Really?
Bonnie: Oh, let go of me.
Stefan: What do you care what happens to Elena, huh? In a minute you're going to be dead, anyway.
Bonnie: And you are going to be human.

Bonnie: Meet Justin Timberlake, audition for American Idol, be on MTV's Spring Break.
Enzo: High aspirations, indeed.
Bonnie: Okay, don't mock my tweener self.

Damon: Update from the outside world.
Stefan: I don't care.
Damon: I do. I care so much it hurts, but it's a good kind of hurt because my lovely humanity is back on and I'm seeing the world through rose colored glasses.

You're right, little brother. I can forgive you for destroying our hometown because I'm not going to let it happen.

Damon

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