Over at the estate, Grandfather Vanderbilt shows his guests the distinguished Vanderbilt portrait gallery and brags about his family’s important roots. He and Nate end up having a heart-to-heart, and he tells Nate that he was proud of him for standing by his mother and compelling his father to turn himself in. Tripp interrupts to offer some touch football.
After showering the Baizen off of her, Blair meets S for some shopping. Blair explains that being the anxious over-achiever was leading her to an early grave, and she’s decided to throw all caution to the wind, and do everything she never would have done before. She starts by shoplifting a pair of sunglasses. Blair walks out, and Serena calls Chuck, blaming Carter for the change. Chuck says he is trying to track dirt on Baizen, but hasn’t found anything. She tells him to set up a meeting with Carter and she’ll do the rest.
On her way to blackmail Carter, Serena sees Lily’s Santa-esque list of bad decisions, and tells her it’s a bad idea to show that to her current boyfriend, because DUH. Lily says she “already agreed” to the list-thing, which is apparently code for: it was entirely her idea, and she bullied Rufus into it. Serena says that if she’s going to do it, which she shouldn’t, she should at least edit it down to be on par with Rufus’s list. The man was once married for 18 years, so… we can guess what that list looks like.
Over at the Vanderbilt estate, Vanessa watches as Tripp and Nate get their expensive sweaters muddy playing touch football. Tripp’s fiancée, Maureen, comes up to Vanessa and tells her not to “fret.” In more evidence that she is some sort of terrifying ghost from the 1930’s, Maureen tells Vanessa that Grandfather has planned out Tripp’s entire life, and will groom Nate similarly into a life of politics and public service. And like Maureen, Vanessa can become a Vanderbilt arm-trophy! Isn’t life grand?
Chuck meets with Carter, who rubs all Blair’s indiscretions in his face, and calls it a game. Serena walks in, and she blackmails Carter, threatening to tell the cops about whatever happened between them in Santorini if he doesn’t leave town ASAP. Her plan works, but Carter warns that he’s not to blame for Blair’s unraveling. Getting rid of him won’t get their friend back.
Lily and Rufus meet for their dinner date, and Rufus hands over his index card with about a dozen names on it. Lily, clearly screwed, reaches into her bag and hands over half her list. Rufus says he’s relieved that they’re in the same ballpark. Later, looking through Lily’s purse for some take-out money, Rufus finds the other half of the list and confronts her with it. She gets mad at him for being relieved when he saw her condensed version, and he gets mad that she lied (and is also a floozy) and leaves. He later returns with a new list of everything he knows Lily loves—the only list he needs to know. They make up. And that’s how our mature grown-ups on Gossip Girl spent their week.
Back to the real story. Dan and Vanessa come home from the estate, and Vanessa worries that Nate will have his life laid out for him, but she doesn’t want to say anything to keep him from reconnecting with his family. Dan tells her to just tell him.
Meanwhile, Blair sneaks off to an unknown house, and Serena and Chuck go to Blair’s and convince Dorota to tell them where she is. They think she’s at some dangerous party.
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