Guest Stars Caitlin Thompson as Madison Elizabeth Perkins as Janet Malone Susan Santiago as Dr. Angela Whitaker Tobias Jelinek as David Watkins Sophia Bush as Lizzie John Legend as Himself Thomas Anthony Jones as Kurt Co Starring Ruben Vernier as PA J. Anthony McCarthy as Building Manager Jamie Tompkins as Third Woman Desiree Hall as Brainy Woman Jenny Tran as Bubbly Woman Eddie Kehler as Mechanic