Kati, Isabel, and Chuck are getting mreow at the door of KOTL, talking about how Jenny -- who, the luxurious camera slide up her body would like you to know, is a hot-ass little girl child -- is a freshman newbie, and Chuck likes freshman because they're "so...fresh" and whatever creeping creepcakes, and they don't even bother to look her up on GG.net, which apparently has a scandal wiki now, which is like the best idea I've ever heard, and then Kati/Isabel (trust me, it doesn't matter) is like, "She won't really make a splash on GossipGirl until you rape her!" And they laugh, and then he sliiiides on over to Jenny's side, and she knows who he is, of course, because all she does is read GG.net and all he does is show up on it, because he's super-rich and wears distinctively stupid scarves. Gossip Girl chooses this moment to giggle to herself about how Jenny's options are to either get Chuck as a boyfriend and thus become cool, or get her ass raped by Chuck, and it's pretty much up to Chuck, isn't it? "I told you I love parties!" she giggles, and sometimes, Gossip Girl, sometimes I hate you just a little bit.
Serena's wearing a totally gorgeous gold gown that would go equally well at a Lincoln Hawk show or at Kiss On The Lips, so like all good shows, we see that the clothes are capable of foreshadowing on their own. She giggles that she's a bit overdressed for walking among the fleshpots of the grunge revolution and Dan totally goes, "Honestly, I don't really have a problem with your appearance." Which is like the cutest thing he's said so far. He drags her over to meet Rufus, and Rufus once again does that "Oh, I know who you are...no I don't!" thing that people do with Serena, and then this awesome Hanson song is playing, and Rufus is making fun of Dan for showing up so early. You know what, how fucked would it be if Jenny and Eric started dating and also Lily and Rufus, in addition to Dan and Serena? That would be like, "What if The Brady Bunch were porn?" Rufus runs off and Serena, apparently unaware of their parents' history together, whatever it is, chuckles about how Dan totally took her to meet his dad on their first date. Dan wows that she just called it that, but quickly recovers. "Maybe I should've worn my loafers, then. Dressed down a little bit." They laugh, because he's poor.
Chuck sneaks Jenny up to the roof and after a funny interchange ("What'd you want to talk about?" "How into you I am.") he starts kissing her. She reacts poorly, so he apologizes and asks to start over. "Um, do you want to start over back at the party?" Jenny asks, which is a pretty good line, but he clarifies that no, he meant he wanted to start over at the beginning of the raping, only this time she should be drunk. So she...takes the proffered champagne and downs it. Jenny's kind of a dipshit, in all honesty. Although to be fair, she re-sends the emergency text from before to her big brother, just in case this obvious scam goes south.
Leaving Lincoln Hawk, Dan gives a telegraphed giggle so Serena will ask what he's thinking, so she does, politely, and he tells her that Jenny was right, and Serena is very nice. Serena wonders why he would ask her out, if he didn't think she was nice, and he corrects her that she is hot, which is enough, and also that she was the one that asked him out on the date. She giggles and then calls him "sensitive tortured-soul boy," which is A) a pretty outdated construction from Lincoln Hawk's salad days, and B) not true, from anything we've yet seen. Nate Archibald seems more like a sensitive tortured-soul boy at this point, and he doesn't even have a soul. But C) is the fact that if they tell you something directly about a character, and it doesn't seem to fit, you're meant to rearrange the whole show around in your mind to make that one thing fit. So now Dan's the tortured-soul boy and I guess that makes Jenny not a dipshit. As they're laughing about how "superficial" it is for Dan not to care whether Serena's smart or nice or anything but a total MILF, Jenny texts Dan a whole message about how she's in trouble "4 real" with Chuck Bass. Not actually that unrealistic -- my sister Katie could text you a novel blindfolded, using only the pad of her rapidly moving thumb, in about an hour, while IMing on a computer and crying on the phone, I've seen her do this -- but still funny, in a way. Dan realizes, because Chuck was mean to him on the bus but also because he reads GG.net and apparently is not a dipshit, that Jenny is in real trouble, so he gets really to take off, but once Serena finds out it's Chuck behind the text messages, she's like, "We gotta get over there at a leisurely pace and take forever to find them. Trust me, this is Chuck we're talking about. He's this really slow, lackadaisical rapist who always gets foiled at the most dramatic possible moment." Dan's like, "See? I should have worn my loafers."