Guest Stars Amanda Leighton as Teenage Sophie Isabel Marcus as Allison Garrett Morris as Lloyd Yetide Badaki as Chi Chi Wendie Malick as Mrs. Damon Natalia Cigliuti as Josie Woods Charlie Robinson as Don Robinson Richard Gant as Albert Jones Kim Staunton as Mrs. Robinson Co Starring Drew Olivia Tillman as Sky Marisa Chen Moller as Pharmacist Phil Abrams as Dr. Weiss Christopher May as Mr. Walsh Taneka Johnson as Woman from the Crowd Sara Montez as Receptionist Truly Magyar as Gas Station Clerk Rachel Brunner as Teen (Arcade Teen) Manley Henry as Man from the Crowd Kay Lumas as Older Woman Luke Clark as Teen Toby Dylan Gage as Little Toby Donnie Berry as John Busner Kate Fuglei as Mrs. Walsh Christopher Guyton as Male Voter Dominick LaRae as Featured Crowd Man Stacy Barnhisel as Amy Pamela Roberts as Doris Jones Maxine Weldon as Featured Crowd Woman Brian Kamei as Pharmacy Clerk Matt Rivera as Messenger