Guest Stars Kiernan Shipka as Sally Draper Alison Brie as Trudy Campbell Christopher Stanley as Henry Francis Anne Dudek as Francine Hanson Chelcie Ross as Connie Ned Vaughn as Ed Lawrence Mark Metcalf as Mayor Johnson Nina Rausch as Gudrun Federico Dordei as Fabrizio Giuseppe Raucci as Luca Joanne Baron as Saleswoman Co Starring Jared S. Gilmore as Bobby Draper Deborah Lacey as Carla Julie McNiven as Hildy Jeanne Simpson as Marilyn Farrelly Edoardo Beghi as Bellboy Josiah Polhemus as Ernie Hudson