Special Guest Stars Joan Cusack as Sheila Jackson Guest Stars Noel Fisher as Mickey Milkovich Jane Levy as Mandy Milkovich Madison Davenport as Ethel Pej Vahdat as Kash Dennis Boutsikaris as Professor Hearst Christopher Gartin as Chip Lishman Paige Lindsey White as Dr. Seery Co Starring Michael Patrick McGill as Tommy Missy Doty as Jess Katherine Cunningham as Danielle Jeffery Self as Grant Jasmin M. Tavarez as Gisela Sonia Jackson as Darla Martini Michael Liu as Hugh Corina Boettger as Pimply Girl Timothy George Connolly as Sleazy Guy Brooke Kuchuris as Mom Bre Mueck as Beautiful Woman