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?

It must be so exhausting overthinking everything, denying your own urge to kill and just be done with them.

Stefan

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.

Vampire Diaries Quotes

Oooh, you know I don't know. Every time we try and go on a date you get kidnapped, I get sent to a prison world, or your feelings get compelled away...

Damon

Damon: My new girlfriend. Andie Starr. Action News.
Alaric: It's not called Action News.
Damon: I know. I like just saying it.