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?

According to the Catholic Church, mortal sin can only be absolved through the sacred act of confession. But it looks like a certain lost Princess found herself in desperate need of unburdening. And who is the man upstairs to discriminate?

Look... I care about three things, Nathaniel. Money, the pleasures money brings me, and you.

Chuck

Yeah I'm sorry about that. But look, if you're done with Blair... be done. Don't cater to your parents wishes if they're not your desires.

Chuck

Chuck: So, where is your head?
Nate: Spinning. I mean, my mom wants me to get back together with Blair so that Eleanor doesn't pull out of the business deal. It's because of my dad's whole trial thing, you know?

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

Serena: You know, we should talk about this though. About us. About eventually.
Dan: Definitely, yes. Yes.
Serena: Or we can just get it over with in a broom closet. (they both laugh)
Dan: In a broom closet? That is...that is rich, Serena.

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.

Looks like the pot calling the kettle black has young Bass boiling over. And if we know Chuck, he's not one to let things lie. Someone pour that man a drink.

Serena: So, do you think we should talk about it?
Dan: Abo--You mean, about, about Vanessa? No, you know what? She's like family, it feels comfortable. So, therefore, she often shows up without calling.
Serena: No, I mean, about what almost, maybe, might have just happened.
Dan: Oh, you mean if Vanessa hadn't entered and we...
Serena: Or we can not talk about it.

Gossip Girl Season 1 Quotes

Better lock it down with Nate, B. Clock is ticking.

Gossip Girl

Mrs. Waldorf: If you're gonna wear one of my designs, at least tell me so we can have it fitted.
Blair: Thanks, mom.