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A disgraced Jenny departs Blair's clique and earns an internship as a fashion designer in a company owned by Blair's mother.
The privileged prep school teens on Manhattan's Upper East Side first learn that Serena van der Woodsen is back in town the way they learn all the important news in their lives - from the blog of the all-knowing albeit ultra-secretive Gossip Girl.
As the Upper East Side teens from Constance Billard and St.
Jude's prepare for a much-anticipated visit from the Ivy League representatives, Blair and Chuck uncover a scandalous secret about Serena that may not remain a secret much longer.
Young Jenny becomes a cunning protege to Blair and Dan enters a relationship with Serena.
It is revealed that their relationship resembles the one between Dan's father Rufus (Matthew Settle) and Serena's mother Lily (Kelly Rutherford) in their youth.
When Georgina arrives on the Upper East Side she poses as a naive woman named Sarah in order to destroy Serena's new found happiness.
She succeeds in exposing Serena's deep-hidden secrets, taking Dan away from her and outing Serena's brother as gay.
Meanwhile, siblings Dan (Penn Badgley) and Jenny Humphrey (Taylor Momsen), Brooklyn-residents, are attracted by the opulent wealth of their classmates.In the midst of all these events, Dan Humphrey greets Vanessa Abrams (Jessica Szohr) back to his life.Vanessa is a childhood friend of his and an outsider herself.Shrouded in mystery and scandal, Serena's disappearance and sudden return are announced by the omniscient blogger "Gossip Girl." The news reaches Blair Waldorf (Leighton Meester) whose life is torn apart when the secret behind Serena's leaving is revealed: Serena was seduced by Nate Archibald (Chace Crawford), the Golden Boy of the Upper East Side and Blair's boyfriend, the night she left town.Nate announces his feelings for Serena a number of times and a series of battles ensue between the former Queen Bee Serena and her heir, Blair.
Once the Upper East Side's most notorious party girl, Serena's reasons for returning are mysterious, although they may have something to do with her younger brother Eric.