Serena: What's Chuck doing today?
Blair: Why are you asking me?
Serena: Well, you guys are friends. And, Blair, you know you can tell me anything. I'd be the last person to judge anyone.
Blair: With good reason.
Serena: Blair, I saw you with Chuck.
Blair: [pauses] I don't know what I was thinking. I mean, sleeping with him once, maybe I could understand. But twice?
Serena: Wait, you slept with him!?
Blair: Shhh.
Serena: Blair!

Serena: You and Nate get back together?
Blair: You mean, since Gossip Girl published pictures of him and some skank?

These butterflies have got to be murdered.

Blair: I can't believe he told her you guys were going to do it.
Serena: Well, I told you.
Blair: That's different, I'm a girl.
Serena: Yeah, well, so is she.
Blair: Exactly my point. But even if she wasn't, when you get a boyfriend, you become the best friend and the best friend becomes the second best friend. That's just how it has to be, if it's ever going to work.

Blair: From this moment forward, the events of last night will never be mentioned again, is that clear?
Chuck: Not as clear as the memory of you purring in my ear, which I have been replaying over and over...
Blair: Well, erase the tape! Because as far as I'm concerned, it never happened.
Chuck: I'll see you at your party tonight.
Blair: You're officially uninvited.
Chuck: Never stopped me before.

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?

Chuck: (sees Blair coming out of church) Well, this is the last place I'd expect to find you.
Blair: Go away, Chuck! I've been given orders, practically from God himself, to avoid you.
Chuck: Would you consider avoiding me over breakfast?

Blair: Losing my virginity to Chuck Bass? None of my friends will ever understand. I'm ready for my punishment. Whatever you and God think is fair. Flogging, fasting, or putting that thing with the teeth around my thigh like Silas.
Priest: How about some food for thought instead? Don't drink, keep your clothes on, try avoiding those who might cause you to stray.

Blair: Forgive me, Father, for I have sinned. It's been... a while since my last confession.
Priest: What troubles you, my child?
Blair: (sighs) After being broken up with my boyfriend for exactly 20 minutes, I succumbed to inebriation, performed at a speakeasy, and surrendered my virtue to a self-absorbed ass. The only good news is that he's a total pig who'll act like it never happened, thank God.
Priest: Ahem.
Blair: Sorry. Truthfully, I'm not even Catholic.
Priest: You don't say.

Blair: Thank you, Father. That was very good advice.... You don't grant birthday wishes, do you?
Priest: I'm a priest, not a genie.
Blair: Well, the next time you talk to Him, could you ask Him to send my boyfriend back to me?

Well, it does have franchise potential. Chuck Bass, I do believe that all your years of underage boozing and womanizing have finally paid off. Truly, I am proud.

Blair: So, I heard on Gossip Girl that you were having sex with Dan out here...in streaming video.
Serena: Oh, God. Kati and Is filmed us?
Blair: Well, it's not very high school musical scandalous. And no, they haven't streamed it...yet. But, I heard it was aggressive.
Serena: I must say, Dan has been surprisingly good at everything we've done.
Blair: Which is? Everything?
Serena: No! But, feel free to ask any personal questions.

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.