Guest Stars Mark Duplass as Brendan Deslaurier Mary Grill as Maggie B.J. Novak as Jamie Stone Randall Park as Dr. Colin Lee Allison Williams as Jillian Eva Amurri as Lucy Jae Suh Park as Anna Co Starring Phoebe Neidhardt as Ashley Jesse Heiman as Riley Cole Hockenbury as Nervous Usher Trisha Beharie as Waiter