Guest Stars Callie McClincy as Holly Holter Charmin Lee as Rose Giles Madelyn Deutch as Dakota Hoon Lee as Dr. Kenneth Park M.C. Gainey as Bob Lee Tergesen as Blake Morrow C. Thomas Howell as Simon Barnes Co Starring Jill Jane Clements as Florence Marguerite Pons as Dot Chris Greene as Oscar Andrea Andrade as Bar Waitress Drew McDermott as Man with Suitcase / Clint Jamie Criss as Twenty Something Cashier