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 Laura Regan as Jennifer Crane Chelcie Ross as Connie Ryan Cutrona as Gene Hofstadt Judy Kain as Olive Healy Pamela Roylance as Irene Ettinger Jud Tylor as Honey Stolich Miles Fisher as Jeffrey Graves Tim Snay as Ronald Ettinger 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