Blair: Did you tell Dan I slept with Chuck?
Serena: What?
Blair: You did You told your low rent boyfriend and he told his social climbing sister who wears my hand-me-downs who blabbed to Nate!
Serena: No, Blair - Dan and Jenny aren't like that. They would never do that.
Blair: You don't get it, do you? The rules are different for the Serena van der Woodsens of the world. People expect you to be party and be wild, sleep with whoever you want, run away, come back...You shot your reputation to hell a long time ago. It doesn't matter what you do but I'm a Waldorf!
Serena: Well since you and your reputation obviously don't need me and my low rent tastes, you and the Waldorf name can weather this storm alone.
Blair: I will.

Blair: Duchess? I'm so sorry, for what I said about the botox. Your work is flawless.

Blair: Forgive me, Father, for I have sinned. It's been...awhile since my last confession.
Priest: What troubles you, my child?
Blair: [Sighs] After being broken up with my boyfriend for exactly twenty minutes, I succumbed to inebriation, performed at a Speak-Easy, 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: [Sarcastically] You don't say?
Blair: But 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, 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: Oh, I plan to. Thank you, Father. That was very good advice. [Gets up to leave but comes back] 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, would you ask Him to send my boyfriend back to me?

Blair: How do you manage to get out of everything unscathed?
Serena: Because I'm nice. You should try it sometime. C'mon, um, compliment me, tell me my hair looks beautiful.
Blair: But your hair looks disgusting. Did you even shower today?

Blair: I know you're here with Chuck, and I can only imagine what he said about me. Limo sex, social torture, freshmen, blackmail. But I assure you, there's an explanation for all of it.
Catherine: Save your breath, Blair. Chuck didn't tell me a thing.
Blair: He didn't.
Catherine: I told him it didn't make any difference to me, because ... despite your best efforts, which are completely transparent, by the way, Marcus will never end up with a lowly Waldorf.

Blair: I would be in my cabana at the Hotel du Cap, and there he would be. Amid all the fireworks on Bastille Day, all I could see was that... Chuck Bass-tard!

Blair: If you didn't pay your rent with it, what did you do with Chuck's money?
Vanessa: I may have created a medical grant for teens with genital herpes. In his name.

Blair: Is something wrong?
James: You're just using me to make that guy jealous.
Blair: I ...
James: It's no wonder you hate Charade. It hits too close to home.
Blair: Chuck is an awful person. He does terrible things. He uses people
James: And you think you're any different? I can't believe I've been so stupid. I bet you don't even like me at all.
Blair: Not really. I mean... you're kinda boring.
James: Am I? Or are you just too interested in yourself to get to know me? You two deserve each other.

Blair: Is that a bong, Mother? I didn't take you for a stoner...

Blair: Is there a reason you're here?
Serena: Stay. Don't let these things make you run away like it did me. Like it does everybody in our world.
Blair: Every thing's horrible. My whole life is falling apart.
Serena: So, rebuild it. You're a Waldorf, remember? People don't tell you who you are, you tell them. Stay and fight. I'll fight with you.
Blair: I'm so embarrassed. I'm so...
Serena: So, what? Start over. It can be done, I should know. We can get through this together.
Blair: Promise?
Serena: Promise. [hugs Blair]

Blair: It's like Roman Holiday but I'm Gregory Peck and he's Audrey Hepburn!

Blair: Martini?
Jenny: No thanks, I don't like vodka.
Blair: Well, that's good. Because this is gin, as it should be.

Blair: My, my. If it isn't Little J, risen from the ashes.
Jenny: I came to tell you in person. You win.
Blair: Oh, sweetie, we just started to play.
Jenny: No, you don't understand. I'm done. With you, with them - all of it.
Blair: Just like that, you wave the white flag.
Jenny: I lied. And I stole and I lost the respect of my family. For what, so I can be like you? You asked me before if it was all worth it. And my answer is, it's not.
Blair: I tried to warn you. There's a price to pay. I always knew a girl like you couldn't afford it.
Jenny: Well, you were right.
Blair: [sighs] Well, you put up a good fight. For a freshman.
Jenny: Thanks.
Blair: [sarcastically] Hope you don't expect a hug.
Jenny: I don't expect anything anymore.

Blair: No one ever enjoys their first time.
Chuck: Except you.

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.
Blair: But you've talked about it, right?
Serena: No, mom! We haven't.
Blair: May I remind you that this is your first real boyfriend, S. And in relationships, you talk about stuff.
Serena: I know, but, I don't know. Sometimes talking about it or planning it can ruin a good thing, you know?
Blair: I would know. Well, as long as you're not worried.
Serena: Well, I'm not. But, I don't know, he might be. Is it possible for a guy to want to slow things down?
Blair: Only the guys we like. [They both laugh] But with you, I can't imagine why.