Guest Stars Kiernan Shipka as Sally Draper Jared Harris as Lane Pryce Christopher Stanley as Henry Francis Mark Moses as Herman "Duck" Phillips Anne Dudek as Francine Hanson Abigail Spencer as Miss Farrell Chelcie Ross as Connie Kristoffer Polaha as Carlton Hanson Joseph Culp as Archie Whitman Erin Sanders as Sandy Jacqueline Hahn as Charlotte Stevens Susan Krebs as Cynthia Trever O'Brien as Doug Co Starring Jared S. Gilmore as Bobby Draper Alexa Alemanni as Allison Jeanne Simpson as Marilyn Farrelly Dani Repp as Waitress