Blair: You know what? I'm tired of this. Go ahead and tell him.
Chuck: Really? You want me to tell him how you slept with me and then faked your virginity for him?
Blair: I'll just tell him your lying. And you do you think he'll believe? You who bangs anything in his field of vision. Or me, his pure and honest girlfriend of many years.
Chuck: I know he'll believe me.
Blair: Why?
Chuck: I have proof.

How about I turn that one-piece to a no-piece?

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.

Blair: Isn't there someone else you can torture?
Chuck: Probably, but I choose you.

Chuck: You know, if my dad and your mom come back from South Africa tomorrow engaged we'll be brother and sister. And you know what they say, the family that plays together stays together.
Serena: Ah. Incest, the universal taboo. One of the, uh, only ones you haven't violated.
Chuck: I'm game if you are.

[to Dan] What do the Humphreys have to offer? Your dad's cassingle?

Chuck: Poor little Humphrey Dumpty. Look, let me clarify something for you. Regardless of who you're currently sleeping with, you and I come from different worlds. In my world, if I'm suspended or expelled, a wing is donated in the Bass name.
Dan: That sounds like quite a world.
Chuck: It's not perfect, I'll admit.

Vanessa: You're sick!
Chuck: You're welcome!

Who knew B and C were such patrons of the arts? Call it philanthropy or bribery, it looks like everyone has their price.

Gossip Girl

Serena: There's no moving on just yet. The pregnancy test wasn't for me, it was for Blair.
Chuck: What?
Serena: She won't take it. So, given that if she's pregnant and you're the father...
Chuck: No! We used a condom.
Serena: Well, obviously it broke.
Chuck: What's obvious is that your best friend has kept you in dark.
Serena: What are you talking about?
Chuck: I handle my business. Apparently, Nate doesn't.

Serena: Hi, Chuck.
Chuck: Please, call me brother.

Chuck: Serena look effin hot last night. There's something wrong with that level of perfection. It needs to be violated.
Nate: You are deeply disturbed.

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.