Guest Stars Megan Ferguson as Wendy Fineman-Walsh Luke Kirby as Davis Calloway John Benjamin Hickey as Roy Sachs Elizabeth Lail as Lola Morgan Donna Murphy as Headmistress Vivian Burton Carla Hall as Rocky Rana Roy as Reema Jeremy O. Harris as Himself Paul James as Aaron Co Starring Bruce Faulk as Jimmy Jakob Von Eichel as George Tom D'Agustino as Fabrizio Ann Harada as Linda Frank DiLella as Himself Douglas Everett Davis as Henry Schacter Tamer Mohammed Abedrabbo as Teymour Erin Lindsey Krom as Linda Schacter Stephanie Tear as Server Tenzing Kalden as Woman Oskar Eustis as Himself David Binder as Himself Uncredited Kristen Bell as Gossip Girl