Special Guest Stars John Slattery as Roger Sterling Guest Stars Robert Morse as Bertram Cooper Anne Dudek as Francine Hanson Andy Umberger as Dr. Arnold Wayne Darby Stanchfield as Helen Bishop Kate Norby as Carol McCardy Teddy Sears as Kicks Matherton Shayna Rose as Rosemary Co Starring Kiernan Shipka as Sally Draper Alison Brie as Trudy Campbell Julie McNiven as Hildy La Monde Byrd as Hollis Maxwell Huckabee as Robert Draper Susan Grace as Delia Allison Fleming as Round Mom Flora Plumb as Gaudy Hat Gary Ballard as Waiter Doug Hale as Charlie