I need a drink. And a buddy. And right now you are my only buddy available to drink. I’m overlooking the fact that you nearly killed me the last time we hung out.

Bonnie

Enzo? Remember Thanksgiving in 1953? We were locked up and I told you I was thankful for you through that little hole in the wall. I take that back.

Damon

Damon: Go ahead. Let it all out, Bonnie. I’m a vile cheater. I couldn’t even wait a year.
Bonnie: Are you kidding me? The last thing anyone wants to deal with for the next six decades is a cranky, bitter, sexless Damon Salvatore, okay?

I’m not letting you kill an old woman whose cold-blooded, ruthless mission is to eat a gingersnap.

Bonnie [to Mary Louise]

Enzo: You missed me! That warms my heart!
Bonnie: I didn’t miss you. I’m curious as to your recent whereabouts. There’s a difference.

Mary Louise: Since when do you eat disgusting garbage food?
Nora: Since I stopped caring about getting that exact reaction.

You know, we’re not meant to like each other, you and I, so thank you.

Caroline [to Valerie]

Julian: You’ve driven away every soul who has ever cared for you.
Damon: I guess I’ll have to cuddle up next to the fire with all my rage.

You made a wrong turn, brother. This isn’t some hell survivor support group.

Damon

I guess it’s safe to say I lost my soft side.

Matt

What happened to your Hero Hair campaign to protect Mystic Falls?

Damon

Here’s the thing, Damon. Hell messes with you, but post-Hell is much worse.

Stefan

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