Guest Stars Zuzanna Szadkowski as Dorota Kishlovsky Margaret Colin as Eleanor Waldorf Reed Birney as Mr. Prescott Krysta Rodriguez as Jordan Steele Matt Burns as Leader of the Yale Skull and Bones Byron Jennings as Dean Berube Co Starring Alexandra Carl as Laurel's Assistant Charlie Hewson as Yale Guy Aaron Dean Eisenberg as Bones Molly Camp as Girl (Ms. Steinberg) Jenny Sterlin as Shirley Bill Kux as History Professor Roarke Walker as Skull Uncredited Kristen Bell voices Gossip Girl