Watch Gossip Girl S05e01 May 2026

: Debuts as the mysterious media mogul Diana Payne. Michael Michele : Appears as Serena's Hollywood boss, Jane. Hugo Becker : Continues his role as Prince Louis Grimaldi. Yes, Then Zero | Gossip Girl Wiki | Fandom

: Where Dan is confronted by his mentor about the Vanity Fair piece. Guest Stars Watch Gossip Girl S05E01

: Blair and Prince Louis return from Monaco to plan their wedding, but Blair clashes with her future mother-in-law over traditions like the wedding dress. : Debuts as the mysterious media mogul Diana Payne

: Nate begins a secret affair with Diana Payne, an older woman with hidden motives who eventually hires him for The New York Spectator . Yes, Then Zero | Gossip Girl Wiki |

: Traumatized by his breakup with Blair, Chuck adopts a philosophy of saying "yes" to everything, leading him into dangerous stunts and a motorcycle accident.