S1, E16: Georgina (recurring guest star MICHELLE TRACHTENBERG) informs Serena that she is prepared to reveal damaging information from Serena's past, but no one is ready 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 (recurring guest star JESSE SWENSON), 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. Plus, one of the Upper East Side teens reveals that he is gay.