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Gossip Girl takes pleasure in reporting that Serena van der Woodsen was spotted buying pregnancy tests. Of course, on the Upper East Side, the truth is often even juicier and more scandalous than the gossip, and this time is no exception. Later it is revealed that Serena bought the pregnancy tests for Blair, who is unsure of who the father would be – Chuck or Nate. Chuck’s jealously over Nate and Blair’s reconciliation pushes him to reveal a few home truths to Gossip Girl and knock Queen B off her throne and end his bromance with Nate.

Having been recently dethroned as Queen Bee in the last episode by Gossip Girl, with an assist from scheming “little J”, Blair hesitantly returns to school with the support of her BFF, Serena. Meanwhile, Serena struggles to adjust to her new living arrangements with her future step-brother, Chuck, while receiving disturbing packages from an unknown sender. Jenny’s drive to be popular hits an all-new time high when she does something illegal to fit in with her new Upper East Side friends.

Serena’s Upper East Side world is turned upside down when her former partner in all things bad, Georgina Sparks, returns to Manhattan to stir up trouble and Serena’s past. When Dan notices that Serena seems preoccupied he jumps to the conclusion that it must have something to do with Serena’s new roomie and soon-to-be step-brother, Chuck. Nate finds romance with the last person he was expecting to connect with, Vanessa. Jenny meets a new guy, Asher Hornsby, who just might be her ticket to permanent popularity. Finally, Blair hatches a secret plan to sabotage her biggest rival, Nelly Yuki.

Georgina informs Serena that she is prepared to reveal damaging information from Serena’s past, but no one is prepared for what Georgina does next. Blair and Jenny escalate their “popularity war” by spreading scandalous rumors about each other through Gossip Girl. Dan witnesses Jenny’s new boyfriend, Asher, cheating on her, but Jenny refuses to listen to her brother’s warning. Rufus goes to Lily for advice on how to handle Jenny’s recent out-of-character behavior.

As a result of Georgina revealing the true reason that Serena fled Manhattan for boarding school, Serena falls back into her old habits and Blair, Nate and Chuck must put their complicated feelings for each other aside to help their friend. Unfortunately, Serena is too ashamed to share the truth with Dan, leaving him only to assume the worse about his girlfriend. Rufus is thrilled 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.

With her best friend Serena’s life and reputation on the line, Blair decides to take matters into her own hands in dealing with the manipulative and evil Georgina. With Rufus never far from her thoughts, Lily 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, but will it prove to be too late to save their relationship?