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Serena slips back into her old habits because she is ashamed of her secret. She eventually reveals it and her friends Blair, Nate and Chuck have to put their differences aside, in order to help her. Unfortunately, Serena is too ashamed to share the truth with Dan, therefore he assumes the worse 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

Georgina informs Serena that she can reveal a deep dark secret from Serena’s past, but no one is prepared for what Georgina does next. Blair and Jenny’s power struggle continues when each of them start spreading scandalous rumors about each other on Gossip Girl. Dan sees Jenny’s new beau, Asher, cheating on her, but Jenny doesn’t believe him. Rufus goes to Lily for advice on how to handle Jenny’s new behavior. Serena tries to confront Georgina, but she leaves before Serena has a chance. After this Serena says that she and Georgina are not friends.

Serena’s world descends into 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 to be 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 to find she is still on the outs with her old friends. Dan visits his mother over Spring Break, and when he returns Jenny is on the verge of becoming a full-fledged member of the A-List crowd. Jenny must go to dangerous and even illegal lengths to fit in. 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 pregnancy tests. Of course, on the Upper East Side, the truth is often even juicier and more scandalous than the gossip. Nate finds out about Blair and Chuck’s affair. And when everyone else finds out what happened Blair’s life comes crashing down. Meanwhile, Dan struggles to tell Serena those three special words.

Serena, Blair, Nate, Chuck and the rest of their friends 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 keep silent, 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. While working on a documentary project about private schools, Vanessa accidentally captures Blair and Chuck discussing their affair. Meanwhile, Lily tries to tell Rufus how she really feels about him.

Blair’s father, Harold, 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 forever. Jenny and Vanessa help Serena get the best Christmas present ever for Dan, who has a surprise of his own for Serena. Then when Chuck texts Blair that Nate is with him in Monaco, Blair worries that Chuck may tell Nate about their hook-up. Meanwhile, Rufus refuses to remain the understanding husband any longer after Alison’s former lover calls the house.

May I have this dance?

Serena has no intention of attending the upcoming Debutante Ball, until her grandmother, CeCe, announces that she simply must go. Unfortunately, Dan isn’t exactly who CeCe wants as an escort for Serena, and she makes her opinion heard loud and clear, causing a rift to form 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. Then a jealous Nate begins to suspect that Blair is seeing someone else. Meanwhile, social climbing Jenny finds herself faced 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.

The Humphreys and van der Woodsens share Thanksgiving!!!

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 complicated romantic past. Meanwhile, Blair’s 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.

It’s Blair’s 17th Birthday Party!

Blair is feeling heartbroken and guilty by the current state of her relationship with Nate and her recent indiscretion. But she manages to put on a happy face for her 17th birthday party and attempts to hide her feelings from her friends. Hoping that Serena and Vanessa can bond, Dan takes Vanessa to Blair’s birthday party, but this ends up making Serena more uncomfortable. Jenny brings her mother home as a surprise, but Rufus isn’t ready to forgive and forget. Finally, Nate’s parents ask him to make a huge sacrifice to save his father’s business as he faces charges of embezzlement and fraud.