Nate: You know, why do I get the feeling you're actually enjoying this?
Chuck: Call me sentimental.

Blair: I have a surprise for you!
Chuck: In that case why are you still dressed?

Nate: But Bart told you your mother died in childbirth!
Chuck: He also told me kids wear suits to kindergarten and blue-chip stocks are great for birthday gifts.

Blair: Enough with the blackmail, aren't you bored already? I can't avoid Nate forever.
Chuck: I didn't say forever, just until the sight of you two together doesn't turn my stomach.
Blair: And when will that be?
Chuck: Only time will tell, I'm afraid. So unless you want dear Nathaniel to know how you lost your virginity to me in the back of a moving vehicle, I encourage patience and restraint.

Did you have a reason for coming to see me? Because if it was to insult me, there's a website you can go to.

He looks like Matthew McConaughey between movies.

Bart: ... A weekend curfew of 1 am.
Chuck: Is that Eastern or Pacific?

Blair: (kicks Chuck's leg) Break a leg.
Chuck: I think I just did.

Blair: We need to talk.
Chuck: I prefer to talk after.

Blair: What was that?
Chuck: I should ask you the same question. Perfect gentleman? Perfect date? That broken record was a hit last year. Get with the times, he bores you.
Blair: You almost made a fool of me in front of the New York Times. Which proves my very point; you can't be trusted. Nate is a gentleman; he would never cause a scene.
Chuck: Never get your blood going, either.

Blair: Squash? I'll squash YOU.
Chuck: It's just a game, Blair.
Blair: Not to me, Basshole. I like him!
Chuck: So do I. And apparently he doesn't have too many friends.

Blair: As tradition on the day before my birthday, I'm heading to the jewelry to put some pieces on hold for Eleanor and...
Chuck: Nate? Oh, I don't think he'll be singing Happy Birthday this year.
Blair: No one knows that Nate and I broke up, and it's going to stay that way until I can fix this. And I don't think you're best friend would still be you best friend is he knew...
Chuck: If he knew how much I enjoyed the removal of a certain chastity belt in the back of this very limo?

Gossip Girl Quotes

Even Blair Waldorf can not bend DNA to her will.

Dan

Hazel: Do you know what you're doing, Little J?
Jenny: I'm not Little J anymore.