Everybody -- including Serena and Nate, I mean everybody -- has taken their finery to DUMBO for no reason at all, instantly, and they're sitting around the one room of the loft doing a reading of The Vagina Monologues all about Jenny's Flower, and it's totally weird, and the police are involved. Jenny comes in looking pissed as shit just as Rufus is getting Zen about her virginity, and she's like, "Guess what, we're not talking about it, and also Damien and I broke up." Rufus is like, "That's sad, but what about the state of your hymen?" Jenny tells then collectively and individually to shut the fuck up about her hymen and leave her alone, and they can just slip the waffles under the door. Everybody stares around and wonders what to talk about.
Serena goes to check on Jennifer and confirm for the eleventh time the state of her hymen, and Jenny pulls a total Jenny and goes, "We totally boned. And honestly I don't see what the problem was or why you were so worried about it. I'm hard and cold and my virginity means nothing." But after she's frozen S out, she puts in her earbuds and listens to "I've Had The Time Of My Life" like a million times and thinks about all the ways it could have gone, where he wasn't a total jerk and she totally did lose her virginity after all. Good for her. There is not a single damned person in that apartment who deserves to know what really happened, after the fucking focus group they put her body through today. Get a fucking hobby, you guys.
So Elizabeth is genetically Chuck's mother -- Or is she? Trust nobody! -- and he apologizes for how hard it constantly, always is for him to let people in, and E points out that he was abandoned as a child, so maybe this makes sense. He's like, "It's important for my emotional health to let people in, but mostly I need you to take over my hotel." She hems and haws and finally accepts, and signs the papers, and it's done. Fucking horror, obviously, in five, four, three...
CeCe calls Lily and tells her in no uncertain terms that it's been too long since she checked in with "the good Dr. van der Woodsen," and Lily begs her to quit with that, but CeCe begs harder, because vdDubs is the only person who can help with whatever it is. And given the oxy last week and the "headaches" she's getting, I can only assume that her ex-husband is the global authority on UES brain cancer, and that's why CeCe has been so complicit in forcing Lily to talk to him this whole time. Still doesn't explain the kissing part, but I'm sure we'll get there; I just think it's hilarious that Lily and Serena's dad would more likely be discussing a serious illness than their daughter, who meanwhile is gallivanting on horseback with her tits out begging either or both of them to pick up the phone and acknowledge her existence. Rufus appears and Lily lies about having to go see her mom at a spa or something, and Rufus says it's a good idea, and when she comes back they can clear the books and start fresh. And I'm as happy as she is to agree, but the look -- abject terror, pain, fear and shame -- that crosses her face when they're hugging and Rufus can't see it? Oh, that's bad. Not my Lily.