Nate brings Jenny her purse and the most effective scene in the entire episode happens. She's staring at the floor on the edge of her bed looking like the ghost of a tragedy and you can't even see her face and she goes, "What's wrong with me?" Like, everything. Nate goes full-on sweet big brother (not like related, more like in the Greek system) and tells her she's going to be fine because look at him: Once he was a hooker and now he's dating Serena van der Woodsen. Jenny starts to slide into depression but then she gets a text from Eleanor offering her a job despite the fact that she is sixteen years of age and was drunk and high and gave all the models pills at the pop-up fashion show. And Nate's like, of course he understands how all the angst and drama just melts away in the face of ADD. They hug, and Jenny remembers how she wants to bone him, and somewhere Serena shivers and doesn't know why. Girl, you need to increase your life insurance coverage or run away with Carter again or something, because Jenny will burn down the Palace Hotel with you in it.
Literally: Dan and Vanessa sit on her gross dorm bed and eat cabbage pierogies. Just the usual crowd of uptown socialites and boho fashionistas. Dan explains to Vanessa that they're doing the same things they always do, but plus fucking, and she reiterates that Friends With Benefits is the name of that, not Lovers, and he says that no, it counts because he gets to call her his Girlfriend, which for boys like him is the only reason girls actually exist. (Also in this conversation, Vanessa interrupts to repulsively nitpick him on what is obviously intended hyperbole. Dreadful girl.) "Humphrey, you just earned yourself some extra benefits," she says for no reason at all, after he's said the same thing he's been saying the entire time, and then they kiss with pierogi-mouth but it's okay because you know those dirty bitches only have one toothbrush anyway. And it's probably Olivia's that she left behind.