Nate tries to get them to let him into Damien Dalgaard's room at the Smythe, and they're not going to, but then he subtly lets the lady in on how Damien's got a sixteen-year-old girl up there. Specifically, the one Nate's destined to fuck, but this lady doesn't need to know that. Meanwhile, in what we think is that room but quickly understand is actually a room just upstairs, in the Empire Hotel -- a genius move to vanish Jenny and her virginity from beneath the eyes of everyone on the show -- Damien and Jenny get down to business. Nate gains entrance into Damien's old room and finds it as vacant as his own mind.
Blair approaches Chuck, post-Doug meeting -- and in the best dress of the evening, a beautiful hip-hugging red number and dripping tiered necklace -- and immediately knows something's wrong. Apparently the boycott is so real that he has to sign the hotel over to somebody immediately, according to Doug the lawyer. I don't know if we've mentioned him enough. So of course Blair is grossed out by Jack's offer to take over, and says she's willing to take it on -- marry her! -- but Chuck notes that "signing the hotel over to [his] nineteen-year-old girlfriend" wouldn't exactly calm people down. Blair suggests the next obvious choice, Lily, but Chuck shakes his head: "She's Bass Industries. The last thing I want is my father's company bailing me out." Okay, valid. But then what? He's not sure, but of course right that second, the NYPD (Is it really? Whom can you trust? Money changes everything!) texts Chuck that Elizabeth is really his mother, and it's Charlie who says there's another choice.
Jenny lets Damien know, finally, after all his pushing and already knowing this obvious fact, that she's a virgin. He says it's "really not a big deal," and she pulls back -- sometimes being a Humphrey is a good thing -- and tries to reiterate that actually, um, it is a big deal. "I chose you," she says. I love how their entire relationship is her acting insane and badgering him into being her boyfriend and fitting into this fantasy she's built around him, and only then being like, "Earn it!" That's so Humphrey.
Damien asks her politely to shut the fuck up and let him fuck her, and she suggests again that this is a big thing, and he offers the compromise that they can talk about it "after," and the whole time he's making moves and rubbing his makeup all over the pillowcases, and finally she's grossed out and decides she doesn't want to do it, and he picks up his skirts and hightails it out of the immediately, tossing back how she's "just a kid." Which... He's been a prince this whole time, and fully tried to talk to her about the V card issue about seven times in this episode, he was above-board the whole time, so this whole about-face is kind of silly, but also totally real. Jenny cries and feels just terrible in every possible way, alone in the hotel room.