Guest Stars Tessa Albertson as Caitlin Miller Mather Zickel as Richard Aasif Mandvi as Jay Mallick Meredith Hagner as Montana Goldberg 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