Guest Stars Clare McNulty as Chantal Witherbottom Christine Taylor as Gail Shalita Grant as Cassidy Michaela Watkins as Polly Jay Duplass as Elijah Co Starring Phoebe Tyers as April Charlie Covey as Reid Conor William Wright as Aaron Jane Gabbert as Kathy Paul O'Brien as Frank Bonnie Milligan as Kathryn Witherbottom Catherine Lloyd Burns as Linda Witherbottom Connor Ratliff as Ted Busby Jim Santangeli as Garrett Shunori Ramanathan as Steph Lisa Haas as Meg Natalie Leer Walker as Gloria Ali Wentworth as Rich Woman Sonia Mena as Press Member Pat Kiernan as Himself Vanessa Aspillaga as Castillo Isabelle Pierre as Prison Guard #2 Pamela Monroe as New Yorker Elizabeth Rich as Inmate Omar Perez as Prison Guard #1