The return of "it girl" Serena van der Woodsen (Blake Lively) to the Upper East Side serves as the first season's focal point. 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 slept with 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. However, the rift resolves in reconciliation between the two and temporary peace follows. Meanwhile, siblings Dan (Penn Badgley) and Jenny Humphrey (Taylor Momsen), Brooklyn residents, are attracted by the opulent wealth of their classmates. Young Jenny becomes a cunning protégée to Blair while 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. As a subplot, Blair and Nate suffer problems in their relationship when the dangerously seductive Chuck Bass (Ed Westwick) conquers Blair's fragile heart. The manipulative Georgina Sparks (Michelle Trachtenberg) arrives, creating a lot of trouble and revealing the real reason behind Serena's disappearance: a death Serena thought she was responsible for. When Georgina arrives on the Upper East Side she poses as a naive girl named Sarah in order to destroy Serena's newfound happiness. She succeeds in exposing Serena's deep-hidden secrets, taking Dan away from her, and outing Serena's brother as gay. At the same time, Blair falls for Chuck, but as a price they both lose their friendships with Nate. Not able to withstand the vulnerability that a real relationship demands, Chuck deserts Blair. In the midst of all these events, Dan welcomes Vanessa Abrams (Jessica Szohr) back into his life. Vanessa is a childhood friend of his and an outsider herself. She is a threat to his feelings for Serena, until he realizes the real love he has for Serena. At the end of the season, the Upper East Siders team up to expose Georgina and banish her from New York. Serena then leaves with Nate for the Hamptons, while Chuck abandons a heartbroken Blair. Dan reconciles with Vanessa and returns to his old life in Brooklyn. A disgraced Jenny leaves Blair's clique and earns an internship as a fashion designer in the company owned by Blair's mother.
- ConditionGood