[to Elena] The fact that you suck at torturing people is nothing to be ashamed of. That's why you have me.

Oh, look at that! St. Stefan has a plan. Let me guess, whoever's holding the kitten gets to talk about their feelings?

Well, Matt lives to hate vampires another day, Stefan's on Caroline duty, and I just introduced Mom to Uber. I'm taking bets on which one goes South first.

Damon: You get a night, Stefan. A night to beat yourself up, do your shame spiral, and then you have to go after Caroline.
Stefan: I don't need a night. I'll find her.

Damon: Eh, a hundred and fifty years is a long time to care.
Elena: Says the guy who pined for Katherine Pierce for a century and a half.

Lily: I took your advice and I've been dabbling on Stefan's computer. What a wondrous invention -- all that knowledge.
Damon: And videos of cats riding robot vacuum cleaners.

[to Elena] You're lucky you're adorable because your eternal optimism is super annoying.

Elena: [to Lily] You've been in here for over a century.
Damon: Yeah, I would've come by sooner but I thought you were safe and sound in the family crypt. My bad.

Lily: Damon?
Damon: Hello, mother.

Elena: Is this presentable attire by 1903 standards?
Damon: Whoa, who said you were coming?
Elena: To meet the woman who gave birth to the two epic loves of my life? Me.

Listen, we go in, we grab my mom, she flips Stefan's switch, he triggers Caroline, emotional dominoes, heyyyyyyy! Everybody wins.

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

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