Guest Stars Luke Kirby as Davis Calloway John Benjamin Hickey as Roy Sachs Elizabeth Lail as Lola Morgan Donna Murphy as Headmistress Vivian Burton Angelic Zambrana as Tati Gardinier Edmund Donovan as Scott Kovacs Margaret Colin as Eleanor Waldorf Jeremy O. Harris as Himself Wallace Shawn as Cyrus Rose Aaron Schwartz as Vanya Zuzanna Szadkowski as Dorota Kishlovsky Co Starring Brennan Gomillion as Harris Victoria Lily Robertson as Sophomore Girl Brianna Keilar as Herself Melissa Lehman as Bar Hostess Aubin Bradley as Ana Serena Berman as TA Nate Washburn as Micah Scott Richard Foster as Constance Coach Ruby Goodman as Stan #2 Tyler Arrington as Isiah Gayla Kornbluh as Freshman Girl #1 Shira Fisler as Freshman Girl #2 Yili Jin as Fan Marcel Werder as Crowd Member Luka Danilovich as Leo Delaney Grace Coyle as Stan Leader Nicole Biello as Stan #3 Uncredited Kristen Bell voices Gossip Girl