[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.

Jo: I've thought about it and anyone named Alaric should not be allowed to name another human.
Alaric: I didn't name me!

[to Caroline] You are an embarrassment to humanity-free vampires everywhere.

Stefan

Stefan: Neat, organized Caroline staying within the lines. Good at control, terrible at revenge.
Caroline: I dismantled your bike.
Stefan: I tore your director's head off with my teeth.

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.

Kai: Damn. Crocodile Dundee called. He wants his knife back.
Bonnie: You know, he's no longer a thing and neither is that joke.

Kai: Don't you ever dream about time travel?
Bonnie: I would rather die of cholera than spend an afternoon with you.

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

Damon

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

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.