| Serena (Blake Lively) returns from her trip to Spain with Poppy (guest star Tamara Feldman) and Gabriel (guest star Armie Hammer). Blair (Leighton Meester) makes a secret deal with Nate's (Chace Crawford) grandfather, William (guest star James Naughton), and Nate learns some disturbing information about his father's arrest. Dan (Penn Badgley) takes a job as a cater-waiter to earn money for college, but is distressed when he discovers the gig is a Passover seder at the Waldorf penthouse and several of his friends and family are guests. Taylor Momsen, Ed Westwick, Kelly Rutherford and Matthew Settle also star. | Tonights’s episode starts out with Blair dreaming that she is Eliza Doolittle from My Fair Lady. What a surprise! We learn that Nate’s cousin is getting married and Blair is hoping to get the fiancee’s help getting into the Whitney Junior Committee, a New York socialite club. Eleanor is not happy about this, and Cyrus is busy preparing a Passover Seder.
Serena tells Chuck that she had a great (and tame) time in Spain with Poppy and her bf., Gabriel Chuck then tells Serena he saw Poppy in town last week, proving Serena’s story to be impossible. Hmmm…what is she hiding?
Nate has a big surprise for Blair: that he got in to Columbia…all on his own, without his family’s connections. And Nate’s cousin’s fiancée tells Blair the Whitney Jr. Committee did not choose her. Nate’s grandfather convinces Blair to tell Nate that he should go to Yale, and he promises to get her into the Whitney Junior Committee …and to be a bridesmaid. And he makes good on both of those promises.
Jenny is working on a science project with a new boy, Wes, that she may have a little crush on. The Humphrey’s are still thinking of ways to get the money for Dan’s Yale tuition, and Jenny’s friend, Wes’s mom owns a catering company and Dan gets a job there. So, Dan’s catering job, of course, turns out to be the Seder and although he tries to get out of it, he is stuck doing it.
Lily is furious with Serena for taking off for Spain after she trashed the house at Jenny’s birthday party. Serena calls Cyrus and tells him she needs a lawyer…cause apparently she got married in Spain!!! Of course Dan walks by just at the perfect time to catch that last sentence. Serena explains that after some wine and some skinny dipping, she “accidentally” wed Poppy’s ex, Gabriel. Dan is clearly offended.
Jenny and Wes are playing monopoly in the living room when Chuck comes in with a bang, making out with some chick and telling them to ignore any screaming they might hear. Gross. Chuck later realizes that he has already hooked up with this girl (a ballerina) last year. Chuck is rude to Jenny, and she tells him off for being a jerk to her at the Kiss on the Lips party last year and not having any real friends or family.
Nate tells Blair that he is refusing to go to Yale because he only got in because of his family. At the Rehearsal Dinner, Nate calls his grandpa out in front of everyone for getting his dad investigated and ruining his family. Grandpa then tells Blair she had better fix the problem…and fast. Nate is just upset because he trusted his grandfather and he looks to Blair for comfort. She chooses the moral high ground and is supportive of her boyfriend, rather than arguing on behalf of his grandfather. His grandfather apologizes for turning his father in, and just then he tells Nate about Blair and their deal. And you know how that is going to turn out… Nate tells Blair he can’t trust her anymore, and we are left to assume they are over.
Lily invited herself to the Seder so that Rufus could hobnob with high-end art collectors. And Serena and Dan lie, telling everyone Blair invited them. Serena tries to tell Dan that her marriage had nothing to do with him, and he has a hard time accepting that. Then who else should stop by the Seder, but Gabriel, Serena’s husband, demanding to talk to her. Serena doesn’t want to have anything more to do with Gabriel and claims that Dan is her boyfriend and Dan backs her story up.
Then, the most awkward Seder in history occurs: Dan is pretending to be a guest while actually being a server, Serena is pretending her and Dan are together in front of an angry Lily and Rufus, Rufus is being insulted by a fancy art collector, Eleanor is being silently judged by Cyrus’s mother, and Cyrus is going painfully slow through the traditions and most of them are being ignored.
Gabriel doesn’t believe that Serena and Dan are dating, and they pretty much have all eyes on them so Dan confesses to being a cater waiter to Rufus. Serena and Lily hash it out in private, and Serena tells Lily she needs a little more freedom in her life and they agree on that. It turns out Serena got into Brown.
Gabriel takes off and when Serena goes after him and tells him she is not ready to be married, he tells her they are not married, they just got drunk and were playing around. They are about to kiss when Blair shows up and needs a hug.
Nate comes over to his old friend Chuck’s place and tells him what happened with Blair. They agree that Blair is changing because she chose Nate over Chuck. Chuck says she just needs someone to believe in her. Nate takes this to heart and takes off.
Rufus decides to sell the gallery. Chuck apologizes to Jenny and she feels bad about what she said to him before. Blair apologizes for blowing off the Seder, and accepts an interview with Cyrus’s contact at NYU. Nate comes to see Blair and she apologizes, and they make up.
Meanwhile Serena is leaving a sweet voicemail for Gabriel, while he and Poppy ignore her call.
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