Vanessa says that at least the truth would be honest, but then S watches as Dan admits that Vanessa's too-cool-for-school propaganda still carries some weight with his stupid ass, because he was embarrassed to tell Vanessa all of that because she disapproves of...masked balls. Proving that Vanessa is a halfwit, but also: Do not apologize for your life! They never listen! (They are in the TV!) So Dan's like, "So...you followed me here to prove I was lying?" Which is lame and true, but not as lame or true as the thing she says next, in a sarcastic tone that totally underscores how lame and true it actually is: "Yes, Dan, that's why I'm here. I stalked you because I am just so obsessed with you. Wait. Don't stop there. You're the whole reason I came back to New York, 'cause I just couldn't stop thinking about you." Which, okay, I'm wishy-washy, because that kind of hurt my heart a little bit for the jerk, because that's exactly what she wanted to say at the beginning of the night. And it's a no-takebacks kind of thing to say, but now she has said it meanly and hatefully, so she can't ever say it again for real, so she kind of just Vanessa'd herself pretty impressively, and that's sad for her, because no matter what happens, the true thing is off the table forever. So the lesson is, never say anything honest to the people you're dating, because they will screw you with it later. At least, that is what I take away from this scene.
Dan tells her to lay off the sarcasm, instead of falling into her arms and being like, "I knew it!" So she has to keep the mask on and pretend to be angry, instead of crying and putting her arms around him and telling him it was all true, over and over. Which would have been nice for her. So now she's been Dan'd and Vanessa'd, and she takes off, because that is now literally her only option. He follows, and apologizes for the lie, and she busts the mask wide open: "You said you love me." Ouch. See? Too much. The thing about running around in boots made for stomping and being too authentic for your surroundings is that you sometimes say true stuff that you didn't need to say, ask for stuff you shouldn't be asking for, and then you get the answer you came for: "Loved you. In the past. And in a pre-shaving, 16-year-old kind of way. You know? I mean, things have changed." Serena's standing behind him now, watching everything go to hell as usual, with the whole world happening around her and her giant feet stomping everything and everybody without even trying. Vanessa nods at her: "Clearly. Looks like someone's traded up." Her voice breaks pretty brutally. She takes off and Serena's like, "So...that's Vanessa. She's beautiful. That makes me nervous and weird, because apparently she has feelings, and I am not acquainted with feelings to the degree that she's into having feelings, so I'm not sure where I stand at this point." He's like, "Can you hold on one more time so I can chase her down one more time and she can act psychotic one more time?" Yeah, all night we can do that. Eventually reaching Brooklyn at ten-yard intervals, we can do that.
Chuck stands in shorts and undershirt behind a pillar, and it's pretty dark out there, and the scene's pretty short, but there you have it: Chuck naked on the roof, pretty horny but about to feel pretty stupid. Then horny again, because it's Chuck. "Feel free to find me," he prances some more, and Jenny's like, "Found your pants, bitch!" and takes off. With his phone, which is in his pants. So now he's naked on the roof and stuck for good. Which, considering what happened between them before, I'm willing to say Jenny got her revenge after all.