Guest Stars Kiernan Shipka as Sally Draper Alison Brie as Trudy Campbell Christopher Stanley as Henry Francis Peyton List as Jane Siegel Sam Page as Greg Harris Patrick Cavanaugh as Smitty Chelcie Ross as Connie Laura Regan as Jennifer Crane Ryan Cutrona as Gene Hofstadt Judy Kain as Olive Healy Jud Tylor as Honey Stolich Tim Snay as Ronald Ettinger Pamela Roylance as Irene Ettinger Miles Fisher as Jeffrey Graves Co Starring Jared S. Gilmore as Bobby Draper Alexa Alemanni as Allison Deborah Lacey as Carla Jamison Haase as Rick Stolich Amy Scott as Hillary