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Georgina (guest star Trachtenberg) informs Serena (Blake Lively) that she is prepared to reveal damaging information from Serena's past, but no one is prepared for what Georgina does next. Blair (Leighton Meester) and Jenny (Taylor Momsen) escalate their popularity war by spreading scandalous rumors about each other through Gossip Girl. Dan (Penn Badgley) witnesses Jenny's new boyfriend, Asher (guest star Jesse Swenson), cheating on her, but Jenny refuses to listen to her brother's warning. Rufus (Matthew Settle) goes to Lily (Kelly Rutherford) for advice on how to handle Jenny's recent out-of-character behavior.
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Gossip Girl (2007) - 1x16 - All About My Brother