Georgie: You don't think I'm crazy?
Ric: You don't even approach the threshold of the crazy I've seen.

Caroline: Is this a bad time?
Ric: No, I'm just getting used to the millennial work ethic.

Damon: So I'm thinking of a person. He's reasonably good looking, charming accent, and he would be the most amazing wingman if he just got rid of his martyr complex.
Enzo: That's not how you play 20 questions. Regardless, your answer is either Jesus Christ, or me.

Look, we can't escape this life, Care. So shouldn't we make sure we're at least living it right?

Alaric

Enzo: Wanna watch some TV?
Damon: Nah, I was just going to read for a little while.
Enzo: Alright. Night then.

Stefan. Hello, brother.

Damon

My life is over, Stefan. My life has been over for a century and a half. Ever since you took it from me.

Damon

Stefan: Please don't give up.
Bonnie: Of course. But please don't ask me to have hope. Hope hurts, and I don't want to hurt anymore.

Don’t tell me what I can’t do.

Damon [to Stefan]

Enzo: I need you to think about me.
Bonnie: No.

Stefan: Well, this looks promising.
Damon: Eh. I’ve seen worse.

Bonnie: If you think this means you’re forgiven…
Damon: I am SO forgiven!

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