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 She giggles and then calls him "sensitive tortured-soul boy," which is A) a pretty outdated construction from Lincoln Hawk's salad days, and B) not true, from anything we've yet seen.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."