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.

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.

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

Elena: Why don't you ever let anyone see the good in you?
Damon: When people see good they expect good. And I don't wanna live up to anyone's expectations.