Guest Stars Aaron Tveit as Trip van der Bilt Hilary Duff as Olivia Burke Holley Fain as Maureen van der Bilt James Naughton as William van der Bilt Deanna Russo as K.C. Cunningham Bree Williamson as Brandeis Simon Miller as Patrick Robinson Co Starring Benita Robledo as Amalia Sonya Harum as Sophie Jimmy Fallon as Himself Amber Bela Muse as Caroline Lowe Christopher Durham as Congressman Wade Annika Pergament as Newscaster Guy Olivieri as Ballroom Reporter Kamahl Naiqui as Student Chip Brookes as Strategist Eugene Osborne Smith as Older Man (Bystander) Uncredited Kristen Bell voices Gossip Girl