Guest Stars Callie McClincy as Holly Holter Madelyn Deutch as Dakota Julia Crockett as Sarah Barnes Hoon Lee as Dr. Kenneth Park M.C. Gainey as Bob 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