Rayna: You want me to go against my very nature because he’s your family?
Damon: Pretty much.

Rayna: What’s next? It puts the lotion in the basket?
Damon: It wouldn’t have to if it just stayed dead.

Doubtful. We only go to New Orleans for crappy booze and Klaus blood.

Once whatever crap Enzo gave you is out of your system and magic works on you again I’m going to give you my blood and heal you. Okay? But in the meantime, there’s something Iw ant you to know. You are a terrible friend, you know that? Do you have any idea what I’d have to go through if you’d died today? Years of guilt. Crippling, self-loathing guilt. Not to mention the resentment I’d feel if I was forced to break in a new drinking buddy. You’re not supposed to die for me, Bon. Neither is my brother. But no matter what I say or how hard I drill it into your skulls, you’re not gonna stop trying, which is why I have to take myself out of the equation. It all ends tomorrow. You’ll never have to worry about me again.

You wanna send me back to Hell? Well let me tell you something, lady. I’m already there.

Huh. You know? You look a lot like my girlfriend and her three doppelgängers.

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: 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?

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.

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

I have no desire to kill Caroline. I mean, not since the last time I tried. I think we can all agree that was a huge misunderstanding.

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