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 Mark Metcalf as Mayor Johnson Ned Vaughn as Ed Lawrence Nina Rausch as Gudrun Giuseppe Raucci as Luca Joanne Baron as Saleswoman Federico Dordei as Fabrizio 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