Damon: If Stefan says he's got it, he's got it.
Bonnie: Do you really believe that or is that just some excuse to continue your slow crawl towards rock bottom?
Damon: Do you know how many days need to tick by before I see Elena again? Twenty-two thousand, nine hundred and sixty one days, and that's if you get some old person's disease. I have not even begun to approach rock bottom.

Bonnie: Do you have any idea how long three seconds are in a life or death situation?
Damon: In the first second, I thought how amazing it would feel to have Elena in my arms again. By second number two, I had kissed her. And by the third, I remembered you're my best friend and that if anything ever happened to you, I would lose my mind. So yes, Bonnie, I do know how long three seconds are.
Bonnie: Just checking...
Damon: I will wait for her. And you're going to help me. You're stuck with me too.

Damon: Every time I look at you all I see is NOT Elena.
Bonnie: I'm so sorry this happened, but I lost Elena too, Damon. And you're one of the few reminders I have of her to hold on to so you can either resent me or love me, but you're stuck with me.

Enzo: Relax, relax. I'm not here to cause mischief.
Bonnie: Says everyone who has ever caused mischief.

I know you, Damon. I spent four months with you, day in and day out. We went to hell and back, literally, and you're more scared now than I have ever seen you before. It's not about what happens if you don't give Elena the cure. You're scared about what happens if you do.

Kai: Damn. Crocodile Dundee called. He wants his knife back.
Bonnie: You know, he's no longer a thing and neither is that joke.

Kai: Don't you ever dream about time travel?
Bonnie: I would rather die of cholera than spend an afternoon with you.

Damon: You don't have to pretend, Bon. I'm like a fever you can't shake.
Bonnie: Yeah, yeah, like a disease.

Coming back to life is complicated. Trust me, I've done it before.

Damon: Kai? If you so much as hurt one hair on her annoying little witch head-
Bonnie: That was so sweet. Why'd you have to ruin it by calling me annoying?

Damon [to Bonnie]: Did you ever think for one second that it's you being negative reacting to my natural self negatively?
Bonnie: You're ridiculous.
Damon: No I'm consistent.

We have this dorm room all to ourselves for a whole weekend and you wanna talk logistics?

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