Damon: Alright, brother. Time to go.
Stefan: Not a minute too soon. This place is dead.

Damon: This is not how you are going to die, Stefan Salvatore.
Stefan: Alone in the wilderness, trapped in the frozen corpse of an alcoholic murderer?

Damon: You want me to say what we both already know? Fine. I’m selfish. I’m angry. I’m impatient. And yes, until I met Elena, I wasn’t interested in doing the right thing for anybody.
Stefan: Your brother included.
Damon: My brother included.

Damon: Are you mad?
Stefan: Yes.
Damon: Do you resent me?
Stefan: Yes.
Damon: Good. Then get up and come kick my ass yourself.

I never fooled myself into thinking that what I had with Stefan would last, but you. You put a ring on it.

Valerie [to Alaric]

To my eyes, you are perfect.

Nora [to Mary Louise]

You're driving. I've got even less time left on Earth than I thought.

Mary Louise [to Nora]

Damon: Now I know why Stefan digs you. You're a take charge kind of girl.
Valerie: And you're a self-serving narcissist.

Hashtag, you're welcome. Are hashtags still a thing? It's been three years.

Damon

Are we friends? I know why you wanted to do this in a letter. So you could desiccate in peace imagining whatever reaction you wanted. Me reading it and thinking “huh, I’m really gonna miss him.” Well too bad. That’s not my reaction. This is. I'm not okay with this decision. I’m not okay with you choosing yourself. And I’m not okay with never seeing you, my best friend, ever again. This hurts me. This hurts.

Bonnie [to Damon]

Stefan: If there is even a fraction of you that cares about me, do not walk out that door.
Damon: Save a bottle of that good bourbon for me, brother. We’re gonna need to sort all this out in about sixty years.

I’m not a good brother when I’m not with Elena and when I’m not a good brother people get hurt.

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