Damon: So Saint Caroline keeps her halo even with no humanity.
Stefan: Yeah, until she snaps and strangles somebody with it.

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

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.

Lily: Damon?
Damon: Hello, mother.

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: 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.

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.

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.

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.

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

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

Damon: What do you think I should do?
Stefan: That's the thing, Damon. I can't tell you. Elena can't tell you. You have to want to be human for yourself.

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.