"I tried it once, but I broke my dad's Gibson. It's very scarring to see your father cry," Dan says, like Rufus doesn't break down in tears twice a week listening to like Pearl Jam. Nate reminds Dan that the Captain never cries because the Captain has only one emotional mode: Dick. He asks Dan if he's going to the Bass/van der Woodsen housewarming, and Dan's like, "Not even invited." Obviously. He has no friends in that house, come on. Nate's sorry to hear that not even Serena has let him off the hook for being disgusting all the time, and says he's just going to chill out and watch pretend movies in his squat using the powers of his imagination. Dan looks at him like a puppy on the street that only wants to be cuddled, and asks where the fuck Anne is. Nate babbles and says he told her negligent ass that he's staying at Chuck's, and then offers to go buy Dan a bottle of water. Dan, of course, allows the homeless orphan to buy him a bottle of water, because he is like this all the time but also so he can call Jenny and spaz out about everything and take on Nate's drama for his very own.
Horace hugs Chuck and pokes gentle fun at his insane outfit before admitting he's impressed: "I know Savile Row when I see it. Joe Kennedy taught me." Chuck turns from offended to deeply moved: "You knew Joe Kennedy?" Yeah, when he wasn't buying presidencies or having people fucking murdered, sometimes he would visit the Brooklyn Inn. "Rumor has it he kept this place in booze during Prohibition. So, you like old Joe?" Chuck names the ways in which Joe K is a personal deity: "Rumrunner, womanizer, millionaire? He was my kind of guy." Horace is charmed by Chuck's ability to fully inhabit the ridiculous persona he has created for himself at the age of seventeen, and takes him down the hall, hand on his back: "Gangsters, fighters, musicians. Dangerous folks, no doubt. But they had style. Something tells me you'd fit right in." Chuck almost bursts into tears at this: the secret thing he has wanted to hear since he was just a little rapist in short pants.
Jenny, who apparently has not moved since... Thursday? finds Dan's dramatic retelling of how he broke into Nate's house to be, you know, a little suspect. "There's just like a sleeping bag and a bunch of Brooks Brothers shirts. Why isn't he staying with Chuck?" She explains people to him again, pointing out how he's obviously embarrassed due to his homelessness. Dan, being unacquainted with the concept of shame or embarrassment on a genetic level, still doesn't understand, so Jenny swings into action. "Okay, look, invite him over for dinner tonight. Dad's making chili. And then once he's here, we can convince him to stay." OMG they are the creepiest. They both want Nate to be their boyfriend, so now they're planning to abduct him in collusion? Somewhere Sandy Cohen is affecting a creepy French accent and quietly singing to himself, "Thank Heaven ... for homeless teenage boys..."