Guest Stars Callie McClincy as Holly Holter Julia Crockett as Sarah Barnes Madelyn Deutch as Dakota M.C. Gainey as Bob Hoon Lee as Dr. Kenneth Park Lee Tergesen as Blake Morrow C. Thomas Howell as Simon Barnes Mark Jeffrey Miller as Pruitt Lyndon Smith as Elegant Woman Co Starring Adam Vernier as Officer Tuttle Lacy Camp as Betsy Austin Marguerite Pons as Dot Chris Greene as Oscar Laura Gardner as Emma Pruitt Drew McDermott as Man with Suitcase / Clint Jason MacDonald as Elegant Man