Guest Stars Tessa Albertson as Caitlin Miller Mather Zickel as Richard Meredith Hagner as Montana Goldberg Aasif Mandvi as Jay Mallick Kate Blumberg as Winnie Co Starring Bill Kocis as Boomer Eastwood Laura Jordan as Carey ("Receptionist") Nichole Yannetty as Woman at Bonfire Wes Shum as Moderator