Kelly: Peter, didn't expect you to be so cleaned up.
Peter: I thought you'd come straight from your workshop with the dagger... the one they asked you to make with Katherine's bones.

Enzo: You don't need pain to keep our connection alive. You are a witch, after all.
Bonnie: A witch who can't do magic.

I know this is a lot for you, Matty, but I miss my family. Don't worry, I won't get all weepy before the drinks arrive.

Kelly

Hi, I'm Katherine, the bitch that will destroy your lives for all eternity.

Damon

Caroline and Bonnie are probably already rehearsing. You don't want to seem unprepared.

Damon

Alright professor, how do we get rid of the Queen of Hell?

Damon

Hey, are you part of my Uber pool?

Uber customer

Damon: It's suicide, Stefan, and if you screw this up, we don't know what he'll do to Elena.
Stefan: I'm sorry Damon, but I have to do this.
Damon: I'm sorry, too, but I can't let anything happen to her, or you.

Enzo: Are you happy?
Bonnie: Right now? Yes, perfectly.
Enzo: Then why not forgive Stefan?
Bonnie: Do you really have to ask?

Damon: Sorry, Blondie, probably best if you don't know.
Caroline: Great, another Salvatore brother freezing me out.

Sorry, this place had the nearest holding cell.

Damon

Kai: Anything else?
Stefan: Damon.
Kai: Aww, that is so sweet, I'll be sure to tell him you were thinking of him when you died.

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