Careful, Stefan, your manhood is showing.

Stefan: What's the point of the jailbreak?
Damon: I thought you needed a hug, Stefan

I happen to like the edge, Stefan. Your problem is your inability to resist falling over it.

Elena: How does he look?
Damon: Pasty and pouty.
Elena: He'll have to get over it.

You’re right. I didn’t have to kill you. I do a lot of things I don’t have to do.

Alaric: You’re going to recycle that same crap-ass apology you gave to Mason Lockwood?
Damon: Yeah, well. I didn’t mean it with him.

Damon: But remember back when you liked me, and we conspired to kill Mason Lockwood?
Alaric: Yeah. And?
Damon: I think he’s still a little pissed.

Tyler can't be helped, at least now while Klaus is alive. Which is, like, always.

Greetings, blondie. Witchie.

You know Stefan. Journaling. Reading. Shaping his hair.

Caroline: How do I fix him?
Damon: Get a new boyfriend.

No one's gonna hurt you, Elena. Especially not my brother.

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

Hey, Blondie. Today isn't the worst day of your life. Today and tomorrow, it's a cakewalk. There'll be people around you day in and day out like they're afraid to leave you alone. The worst day? That's next week when there's nothing but quiet. Just a heads up.

Damon