Lily and Rufus speed away from the scene of the Jack, and she's like, "Did you find the Symbolic Scarf yet?" And instead of apologizing and acting like a man for one single second, he does his usual "Let's go somewhere private."
Some elsewhere private, another Humphrey man has cornered Jenny, and she's like, "Shut up already." Dan calls her stupid and tells her she's sixteen and a girl and a dummy, and she goes, "Yeah, and when you were sixteen, you were in love with Serena, and everyone thought it was adorable." HA! Then Vanessa walks in, looking exactly the same as she always looks, which is beautiful, but the music goes crazy and the camera stutters all over itself and apparently that means she's "hot" right now, so Dan's boner goes over to say hello, and Vanessa is like, "This is a Friends Only Zone, and secondarily, I'm not wearing any underwear." Which is a dumb joke anyway, but one that turns gross and horrifying when it's Vanessa, with her crystal deodorant ways. Dan stares, they're still awesome no matter how much the show has lost its momentum with keeping them awesome.
Meanwhile, Jenny has been sitting unaccompanied for five seconds, so Nate with his sexy slicked hair instantly appears. "Go away traitor," Little J grunts, and he apologizes for calling Rufus and entrapmenting her and being the only person who could manage to fuck up a Serena Plan even worse than Serena, but Jenny's a "really special girl" who deserves a good guy. Jenny points out the glaring obviousness here, which is that the only person who will ever be taking her virginity is Nate and he's currently, for the moment, with Serena, so why even bother, and he explains about the mauling of S at the state dinner, which Jenny blows off so completely, but only on her way to Humphreying the accidental truth that Damien is a massive drug dealer.
I mean, possibly this is her way of begging Nate to save her from losing her virginity, because she tries that shit in this episode fifteen billion ways, but still comes off as a non sequitur. So Nate's like, "Um whaaa" and Jenny calls him a hypocrite because he's always doing drugs, and then -- as Damien appears, sealing the deal -- says the thing that I guarantee you will get you anything you want, at any time, with any boy: "Stop pretending that you care."
(I cannot stress this enough: That is the Key to fucking with boys, because it calls their entire universe into question. It almost feels unfair to say so, is how powerful that shit is. Every boy-- every boy in the whole school -- will fucking lose it if you say them. They are the Goblin King Striped-Cap Spell of Boys. That Groucho Crow drops from the sky with the Phrase That Pays hanging around its neck if you ever endeavor to say those words. Use them judiciously and be prepared for the consequences when they try to prove you wrong. Even if they were pretending to care before, or didn't even think about caring before, this will send them into a violent romantic fit of (500) Days Of Summer bullshit that can only be compared to the Viking Berserker Rage of yore.)