Guest Stars Connor Paolo as Eric van der Woodsen Aaron Tveit as Trip van der Bilt Matt Doyle as Jonathan Whitney Hilary Duff as Olivia Burke Sarah Steele as Kira Abernathy Co Starring Valentina de Angelis as Carmen Fortier Meg McCrossen as Jane Trapp Ben Rauch as Tim Chanel Farrell as Sawyer Jeremy Chu as Harry Beth Fowler as Mistress of Ceremonies Wolé Parks as Staffer Ryan Vigilant as Graham Uncredited Kristen Bell voices Gossip Girl