Guest Stars Victoria Tate as Rena Robinson Shari Belafonte as Julia Johnson Hannah Leder Werntz as Isabella Joe Marinelli as Donny Amber Friendly as Layla Bell Joe Pacheco as Bart Joe Tippett as Hal Jackson Holland Taylor as Cybil Richards Jack Conley as Earl Tig Notaro as Amanda Robinson Aflamu Johnson as Aflamu Stephen Fry as Leonard Cromwell Natalie Morales as Kate Danton Co Starring Aven Lotz as Young Bradley Paull Walia as Sahil Brian Byrnes as Reed Ingrid Walters as Simone Matthew Downs as Officer #2 Jeremy Denzlinger as Desk Officer Rafael Cabrera as Vincent Jason W. Wong as Maître d' Marita De Lara as Sarah John Hartmann as Interviewer Paul Chirico as Bradley's Father Joanne Baron as Brenda Litchfield Uncredited June Diane Raphael as Eagle News Anchor