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With her best friend Serena’s (Blake Lively) life and reputation on the line, Blair (Leighton Meester) decides to take matters into her own hands in dealing with the manipulative and evil Georgina Sparks (guest star Michelle Trachtenberg). With Rufus (Matthew Settle) never far from her thoughts, Lily (Kelly Rutherford) prepares for her wedding day which is destined to be the Upper East Side’s social event of the year. Serena finally pours out her heart and the truth about her past to Dan (Penn Badgley), but will it prove to be too late to save their relationship?
After Georgina reveals the true reason Serena left Manhattan, Serena goes back into her old habits. Her friends Blair, Nate and Chuck-in order to help her-have to put their differences aside. Unfortunately, Serena is too ashamed to share the truth with Dan, therefore he assumes the worst about his girlfriend.
Meanwhile, Rufus is excited when his band is invited to perform at a Rolling Stone-sponsored concert, but Lily is the last person on earth he expects to see at the performance, especially since her wedding rehearsal dinner is the same night.
Serena's world becomes a chaos when a former friend the evil Georgina Sparks returns to town. Dan sees Serena preoccupied and he assumes that it has something to do with Chuck, her soon step-brother. Nate connects with the last person he expected, Vanessa.
Having been recently dethroned as Queen Bee, Blair returns to school with the support of her BFF, Serena. Dan visits his mother and upon his return home he's surprised to meet Rufus' new girlfriend. She apparently spent the night and is now making pancakes in the kitchen. We see Blair at a club alone at a huge table waiting for her friends to arrive, but no one has shown up yet. Jenny's drive to popularity hits when she does something illegal to fit in. The we see her going to sell some of her things to a consignment shop. Serena struggles to adjust to living with Chuck, and receives disturbing packages from an unknown sender.
Gossip Girl reports that Serena van der Woodsen was seen buying a pregnancy test. Of course, on the Upper East Side, the truth is often even juicier and more scandalous than the gossip. Nate finds out about Blair’s and Chuck’s affair
Serena, Blair, Nate, Chuck and their class break into the school swimming pool for a night of fun, but when someone nearly dies, the school threatens to expel the person responsible for the break-in. Everyone agrees to not say anything, but this creates major problems between Serena and Dan, because Dan is not ready to take the fall for someone else and risk his future. Vanessa, while working on a documentary project about private schools, accidentally captures Blair and Chuck discussing their affair. Lily tries to tell Rufus how she really feels about him
Blair’s father comes home for the holidays with an unexpected guest, his boyfriend Roman. Blair cannot hide her disappointment and makes a plan to get rid of Roman. Jenny and Vanessa help Serena get the best Christmas present ever for Dan, who has a surprise of his own for Serena. When Chuck texts Blair that Nate is with him in Monaco, Blair worries that Chuck may tell Nate about their hook-up. Rufus refuses to remain the understanding husband after Alison’s former lover calls the house
Serena had no intention of attending the upcoming Debutante Ball, until her grandmother CeCe announces that she must. Cece does not approve of Dan as Serena’s escort, causing a rift between Serena and Dan. Although they are officially broken up, Nate asks Blair to go to the ball with him. She accepts, but only as friends. However, a jealous Nate begins to suspect that Blair is seeing someone else. Jenny finds herself with the decision of either attending her mother’s art opening or following her dreams to the Debutante Ball, even though her parents don’t want her to go
Dan invites Serena and her family to spend the holiday with his family, creating an uncomfortable situation for Rufus and Lily. The children are unaware of their parents’ complicated romantic past. Meanwhile, Blair freaks out when she learns that her father isn’t coming home for Thanksgiving. Nate spends the holiday with his family, but their awkward dinner quickly goes from bad to worse
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