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.

Bonnie

Lily: Where've you been?
Damon: What are you, my mother?

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

Damon

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

Damon

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

Do you know how many times I've died, or nearly died? Most of those times were at the hands of people I thought were my friends. I'm sorry, not people. Vampires.

Matt

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.

[to Tyler] If Matt dies, are you going to start peeing on fire hydrants again?

Caroline

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.

Damon

Jo: I'm marrying an idiot. You could have died today.
Alaric: As opposed to any other day?

Vampire Diaries Quotes

Elena: I wanna remember.
Damon: Well you're a day late and a dollar short honey.
Elena: I mean I wanna try. Knowing there is this whole piece of my life missing it's driving me crazy, ok? So I have to at least try to get it back.

Damon: You know what they are? Children. Like lighting a candle's going to make everything OK, or even saying a prayer. Or pretending Elena's not going to end up just like the rest of us murdering vampires. Stupid, delusional, exasperating little children. And I know what you're going to say: 'It makes them feel better, Damon.' So what? For how long? A minute, a day? What difference does it make? Because in the end, when you lose somebody, every candle, every prayer is not going to make up for the fact that the only thing you have left is hole in your life where that somebody that you cared about used to be. And a rock with a birthday carved into it that I'm pretty sure is wrong. So thanks, friend. Thanks for leaving me here to babysit. Because I should be long gone by now. I didn't get the girl, remember? I'm just stuck here fighting my brother and taking care of the kids. You owe me big.
Alaric: I miss you too, buddy.