Guest Stars Connor Paolo as Eric van der Woodsen Nicole Fiscella as Isabel Coates Margaret Colin as Eleanor Waldorf Amanda Setton as Penelope Shafai Michelle Trachtenberg as Georgina Sparks Yin Chang as Nelly Yuki Sebastian Stan as Carter Baizen Wallace Shawn as Cyrus Rose Jan Maxwell as Headmistress Queller Matt Doyle as Jonathan Whitney Chris Riggi as Scott Rosson James Naughton as William van der Bilt Reed Birney as Mr. Prescott Stella Maeve as Emma Boardman Co Starring Carrie Yaeger as Teacher Barbara Andres as Bursar Uncredited Kristen Bell voices Gossip Girl