: Traumatized by his breakup with Blair, Chuck adopts a philosophy of saying "yes" to everything, leading him into dangerous stunts and a motorcycle accident.
: Where Dan is confronted by his mentor about the Vanity Fair piece. Guest Stars Watch Gossip Girl S05E01
: The site of a glamorous party attended by Serena, Chuck, and Nate. : Traumatized by his breakup with Blair, Chuck
: Nate begins a secret affair with Diana Payne, an older woman with hidden motives who eventually hires him for The New York Spectator . Watch Gossip Girl S05E01