The Sixteen Year Old Virgin
Despite being grounded, Jenny continues to see Damien who tells Jenny that he wants to have sex with her. Lily tells Rufus the big secret she has been keeping from him even though she knows it's a huge risk. Dan and Vanessa explore a new stage of their friendship. Chuck is forced to make an extremely difficult decision about his hotel.

Cast
Blake LivelySerena van der Woodsen
Leighton MeesterBlair Waldorf
Penn BadgleyDan Humphrey
Chace CrawfordNate Archibald
Ed WestwickChuck Bass
Kaylee DeFerIvy Dickens
Matthew SettleRufus Humphrey
Kelly RutherfordLily van der WoodsenGossip Girl on tvt

