It's autumn in New York, which means that Bart Bass is imposing curfews on his step-children. In order to make up for Serena being a socialite whorebag and Lily being a married-15-times whorebag and Eric being a gay, the family has to hunker down and abide by some rules. Serena, being used to murdering people with cocaine while making a sex tape, balks at this idea and storms out, presumably to purchase more low-cut dresses. I'm not complaining.
Over in the poor person part of town, Vanessa introduces her newest charity case to Jenny and Dan: an old building. It used to be a speakeasy (like 85 years ago, WTF Gossip Girl?), but now that its owner can't pay rent anymore or something, it's up for auction, which means that there's a 75% chance it will be purchased by a rich white person and turned into a Smoothie King. Just so we're clear, it's currently owned by a poor black person. Oh the dichotomy!
Irony alert: Vanessa is POOR, but she's championing a CHARITY CASE related to a FORECLOSED BUILDING. That's like a black fly in your Chardonnay, right there. How unlikely would it be for a similar situation to arise later in the episode? Only time will tell!
Also Nate has invited Dan to try out for the soccer team because they are in love. They pal around a lot in the halls and touch each other lightly on the neck and generally make Chuck jealous. Meanwhile, Vanessa corners Blair and demands that Blair get thousands of signatures for her petition to stop the building from being turned into a Smoothie King. When Blair rightfully tells her to stop being an idiot, Vanessa whips out her cell phone picture of The Lord making out with The Duchess and is all, "What now, bitch? I own you." That Vanessa. What a charmer.
Instead of getting signatures, Blair reminds Chuck that 1) he has no friends and 2) he wants to f Blair. This segues into Cruel Intentions: Chuck has to seduce Vanessa, and if he succeeds, Blair will let him seduce her. The purpose of this is the humiliate Vanessa (for Blair) and get back at Dan for stealing Nate from Chuck. Oh the tangled webs they weave. Something tells me this is going to end with Blair taking a dump on Chuck's chest.
Serena is still surly about the new rules Bart has imposed, and Eric is like, "Seriously, just go along with it and shut up." She decides to listen to Eric, since he is the only wise person on this show, until Chuck tells her that Bart is just trying to make they appear family-like to impress some Midwest clients of his. Those crazy Midwesterners, what with their plumbers and six packs and families and not aborting babies. Serena responds by wearing an awesome dress and telling Bart that she forgot to put on underwear. Because if there's one thing you want your mom's new husband to be thinking about, it's your vagina. While he masturbates.
The next day, Blair and Serena have lunch with Eric and his new boyfriend, Jonathan. Jonathan's character consists of being gay and innocuous looking. Good for him.
Over in Bohemia, Dan brags to Jenny and Rufus about how he totally has a boyfriend now. They're like, "Nuh uh no you don't," and he calls Nate right in front of them, to prove how real their love is. They make plans to play soccer in the park at noon. Therefore, obviously, Dan shows up to Nate's house at noon. There's a big giant "WE'RE TOO POOR TO PAY FOR STUFF" sign out on the front, so Dan breaks in and spies, because he is Vanessa's friend. He calls home and tells Jenny that Nate is squatting in his own home, so Jenny naturally concludes that the best place for Nate to stay is at the Humphrey house. Because, you know, it's not October or anything. Nate hasn't been managing just fine in that house for two months, so he definitely needs the fucking Humphreys to take care of him. That's like entrusting your wellbeing to a herd of cattle. And not cool cattle like from the California cheese commercials, but poor cattle.
Chuck goes to the real estate auction and some hipster throws at rotten tomato at him. Or maybe it's a smoothie. That would be ironic. Either way, he leaves and tells Blair that he doesn't want to try to f Vanessa after all, since she's lame and her friends are smelly. Blair convinces him to keep trying by playing with his balls or something, so he goes back to the speakeasy and hears from its wise black proprietor all about how cool it was back in the 1920s. Which, I mean Prohibition ended kind of a while ago, so it must have been just a regular bar in the interim, which really isn't that big of a deal. Vanessa is an idiot. Anyway, Chuck decides to buy it because he really wants to have sex with Blair. That's sweet of him.
Jonathan shows up to the Bass der Woodsen house and tells Serena that he's not coming to the party because "Bart said it was family only." Serena gets super pissed again, thinking that Bart's rampant Republicanism is keeping Eric from expressing his sexuality freely.
Did I mention the party? Lily and Bart throw a housewarming party. Some people from magazines are there to interview the happy family, plus Vanessa is there to get fucked by Chuck, and Blair is there for the same reason. Serena ruins Lily's life, but before that happens, Bart tells Chuck that Bass Industries will not be buying some piece of shit bar in Brooklyn, aka Vanessa. Chuck is like, "Stop saying I have bad taste!" Blair is super crazy jealous of the attention that Chuck's paying to Vanessa, so she steals Vanessa's purse and deletes the picture of The Lord and The Duchess from her phone. It seems like she could have done that a long time ago. It also seems like somebody should just turn that bar into a Smoothie King.
In a routine Character in Teen Dramedy Reveals to Ugly/Poor Girl that Rich/Popular Boy Has Only Been Dating Her to Win a Bet maneuver, Blair tells Vanessa that Chuck was only dating her to win a bet. Vanessa gets sad and storms off, so Blair declares Chuck the winner of the bet and waits upstairs to have anal sex with him. Chuck is just sort of like, "What."
Meanwhile, over in the derelict section of town, Nate is eating chili with the Humphreys. They try to get him to stay the night, but Nate is like, "Nah, I'm gonna go home. You guys suck." Then Dan confesses to having broken into Nate's house, and Nate's pretty indignant for a guy who used to date Vanessa. He should really be used to that shit by now. At any rate, he rightfully explains to Dan that hanging out at Yale for a weekend and playing soccer does not equal BFF. Nate breaks up with Dan, who cries into Cedric's bosom for a couple of hours, until Rufus tells him that no never means no, and that he should go get Nate and bring him back, because, effectually, Dan is the only friend Nate has. Now at least we know where Dan gets his grossly inflated sense of self-importance.
At the party, Eric tells Serena that it was he who told Jonathan not to attend. Since Bart's name is now cleared, Serena has to dredge up a bunch of hate for her mother in order to throw a proper tantrum. Once she has successfully spoken out about her mother's past husbands' various vices (some of which are simply being named a variation of "Klaus"), she runs out into the street to pout and ends up spending the night talking to Dan Humphrey, who is himself wandering around the UES in search of some Nate Archibald to kidnap. They apologize to each other for being stupid enough to put up with Dan's shit for so long, and then Bart shows up to take Serena home in a limo. You can really tell Dan's matured because he doesn't even make a crack about how black Serena's soul is from all the orphans and pandas who died while stitching together her fancy car.
Serena and Bart arrive back at their house, where they laugh about how shameful Lily's life has been and eat expensive cake made of bald eagle eggs. Dan shows up some time later in Brooklyn, dragging a bound and gagged Nate behind him.
Chuck follows Vanessa back to the speakeasy, where he tells the black proprietor that he wants to buy it, for serious. This impresses Vanessa, who totally wanted to fuck him the whole time anyway. Chuck goes back to Blair, who's wearing lace thigh-highs and satiny red lingerie, and they make out and it looks all sexy and shit, except that Chuck totally ruins the mood by being like, "Tell me you love me," and Blair's like, "Ew, no! Just stick your dick in me," and he's like, "Not until you tell me you love me," and I'm like, "Jesus, 17-year-olds are so picky about sex!" Seriously. He threatens never to bang her until she tells him she loves him, which is amazingly only like the 3rd gayest thing to happen this episode. Even more improbably, Eric's date with Jonathan was the absolute least gay thing. It's like ray-ee-ain.