Special Guest Stars Phil McGraw as Himself (Dr. Phil McGraw) Guest Stars Erick Lopez as Hector Michael McMillian as Tim Esther Povitsky as Maya Burl Moseley as Jim Kittsworth Jacob Guenther as Chris Michael Hitchcock as Bert Buttenweiser Johnny Ray Meeks as Kevin Allison Dunbar as Stacy Whitefeather B.J. Novak as Himself Matt Walsh as Frank Co Starring Debra Cardona as Estella Craig Gellis as Rick Arden Belle as Lana Carrie Clifford as Clarice Doug Mand as David Frank Crim as Jewelry Guy Mark Sande as Board Person Rachel Andersen as Judge