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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.

Hazel and Penelope try to recruit Nelly Yuki to be part of their club but it is not easy. Blair supervises the whole operation and hatches a plan to sabotage her biggest rival, Nelly Yuki. When Nelly breaks down after being reminded of her recent break-up with her boyfriend, the ladies find their way in and Nelly comes to the Waldorf penthouse. Then Blair invites the ex-boyfriend over.

Meanwhile Serena goes out with Georgina, but things get so bad that Serena thinks someone spiked her non alcoholic drink. Jenny develops a crush on a dog-walker, Asher Hornsby, who might be her ticket to permanent popularity.

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. Everyone else also finds out what happened and Blair’s life comes crashing down. Dan struggles to tell Serena those three words.