It's difficult to explain to your brother that you just broke up with the former love of his life and then broke the bed.

I killed him to convince myself that you were right, that I was the type of person who could kill in cold blood and I was never gonna change.

Damon: The second we're cured of this and don't wanna rip each other's heads off, I am gonna hunt you down and give you the most mind blowing night of your life.
Elena: I think I can schedule you in.

Katherine: I'm the one who taught you how to love.
Damon: I'll see you in Hell, Katherine.

What's up, Doc?

Tyler: You're a joke, Damon.
Damon: Says the guy pining for the girl who slept with Klaus.

Bonnie: She would kill you.
Damon: Cool and then me and all her dopplegangers can start a baseball team on the other side.

Stefan: Come on Damon, you're better than this.
Damon: On the contrary brother, I'm better like this.

I happen to like my old sadistic self?

You are literally the best person I've ever known. And for me to think I could ever change you was giving me way too much credit and you way not enough… you're the good. And I need a little good in my life.

Enzo: Do you wanna kill him or should I?
Damon: I hate deadlines.

Damon: You once told me that calling me "Satan" was an insult to Satan.
Caroline: Well... no one's perfect.

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