Chuck (Ed Westwick) is completely unconcerned over the new rules that are giving Serena a headache.  That's because the rules don't apply to him.  They only apply to S, who Bart is worried will jeopardize an upcoming business deal of his by making a big splash in the papers.  After finding this out, S gets dressed to the nines, minus the underwear, and prepares for a night on the town.  Meanwhile, Blair reenacts Cruel Intentions by asking Chuck to seduce and destroy Vanessa.

Eric has a boyfriend!  He introduces Jonathan to Blair and Serena over breakfast the next day, and they're both thrilled over the adorable new couple.  While Jonathan and Eric hang with the girls, Jenny accuses Dan (Penn Badgley) of not having any guy friends.  He proves her wrong by calling his new bro-friend Nate and setting a date.  Dan has also joined the soccer team at school, so it's all guys all the time in his world.  Across town, Chuck surprises Vanessa by announcing that he's ready to buy the old building.  She thinks he's up to some sort of scheme, and of course she's correct.

Lily is upset that Serena (Blake Lively) broke curfew the night before, but S thinks her mom has been brainwashed by Mr. Bass.  The van der Woodsens aren't having an easy time, and neither are the Archibalds.  Dan shows up at Nate's place and not only discovers that the mansion has been seized by the police, but also that Nate has been sleeping there with nothing but a sleeping bag and some supplies.  While Lonely Boy goes to meet Poor Boy in the park, Chuck tells Blair that he's not up for their little scheme.  However, he rises to the challenge the instant B offers to sleep with him if he succeeds.  She obviously has Cruel Intentions on Blu-ray.

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