Guest Stars Kiernan Shipka as Sally Draper Jared Harris as Lane Pryce Sam Page as Greg Harris Crista Flanagan as Lois Sadler Patrick Cavanaugh as Smitty Chelcie Ross as Connie Charles Shaughnessy as Saint John Powell Ryan Cartwright as John Hooker Judy Kain as Olive Healy Carol Locatell as Miss Wakeman Jamie Thomas King as Guy Mackendrick Co Starring Jared S. Gilmore as Bobby Draper Alexa Alemanni as Allison Julie McNiven as Hildy Edin Gali as Kurt Mark Kelly as Dale Neil Dickson as Harold Ford