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Nate promises to help Serena win Carter back from the Buckleys through poker, and eventually raises the stakes to include a picture of Future Congressman Tripp van der Bilt with a van der bong, but they lose...
SO GOOD. So this poor guy has to decide who'll give the freshman toast at NYU Parents' Weekend, and he's got it narrowed down to two girls: the genetic fondue pot that is Vanessa Abrams, and... Blair Waldorf, for some reason. Unbeknownst to anybody, Dan invites the Duffster along, so she accepts the alumnus's original invitation to give the speech in order to surprise him and his family with how down-to-earth she really is.
Also, everybody on the show is wearing the same asymmetrical purple dress and it's super weird. I thought this was another NYU thing but it's not, because Serena is wearing one, and she's now fully made the switch to the Nate Show. After Blair wages serious mental warfare on Vanessa, she gets Dan to uninvite Olivia, then accidentally tells Olivia that he did it because he's embarrassed by her superstar status.
This all comes down the pike because Vanessa's mom -- perfect Gina Torres, from Alias and Firefly -- is twice as Vermontalicious as her daughter, hates NYU for a million reasons including H.R. Dufnstuf, and I guess will only give Vanessa the respeito she desperately needs by seeing her give this speech.
Blair basically wants it because she is: crazy. Having gotten Duffington Post out of the way via the gaping need Vanessa embodies, she sends Chuck in to secure the lips of the alumni liaison -- not to mention a "Previouslies" quote for future seasons when Chuck finally goes gay ("Did you think I'd never kissed a guy before?") -- but then it turns out because the guy just wanted the kiss for a gay scavenger hunt, which is redundant. However, Chuck's upset because he only likes kissing B.
Duffy the Humphrey Slayer eventually drags Dan to the banquet anyway, just so she can embarrass him in front of Lily and Rufus by acting like a Hollywood jerk. Then V tricks Blair into talking trash over a hidden microphone, embarrassing herself plus everybody else, but especially B for not seeing a total cliché heading straight for her head. Her overheard confession, however, includes the part about lying/pimping out Chuck, which hurts his feelings -- especially poignant once Lily points out that Chuck would get frisky with a dude if Blair asked him to, because he is just that devoted to her, so she shouldn't have lied in the first place.
(Meanwhile, on a different show entirely, everything is crazy: Nate promises to help Serena win Carter back from the Buckleys through poker, and eventually raises the stakes to include a picture of Future Congressman Tripp van der Bilt with a van der bong, but they lose. The reason he's willing to risk so much for a guy who once bet him in a poker game would be more confusing if it weren't Nate. But twist! Come to find out the photo is fake, and the whole thing was a Nate/Grandfather plan to discredit the Buckleys -- meaning S totally got played by Nate! She eventually settles Carter's debts by warning the Buckleys, but too late: Carter throws a fit because he wanted to prove he was a man by settling his own debt, and ends up peacing anyway, dropping a surfeit of smolders on his way out.)
Dan and Shia LaDuff figure out that Vanessa has once again stuck her psycho Navajo jewelry in their relationship, confront her, and before she can cry and lie about it like always, the hits keep on coming: Gina Torres overhears Vanessa talking about what terrible parents she has, and bounces back home on a cloud of self-righteousness and authentic maple syrup. The episode ends with Chuck's trust seriously betrayed, S in tears, Olivia eating Humphrey waffles and Vanessa lonelier than ever, sharing a table at the Bleecker with Blair and watching her not eat a croissant. XOXO.
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