Guest Stars Jimmi Simpson as Phil Hayes Kristin Lehman as Therapist Gillian Jacobs as Annie Mitchell Mike Dopud as Annie's Husband Co Starring Emily Chang as Barista Lily Matthew Mandzij as Officer #1 Sara Amini as Julia Simon Chin as Ice Cream Server Lossen Chambers as Mrs. King Nicole Major as Female Passenger Jamall Johnson as Handsome Guy Nagin Rezaiean as Pizza Cashier Emerson Skye Coutts as Chloe (6 Yrs Old) Garth Hodgson as Train Conductor