Guest Stars Jane Adams as Annabelle Jones Jacqueline Toboni as Jo Michael Chernus as Kyle Jake Weber as Wally Gugu Mbatha-Raw as Sophie Jake Johnson as Drew Co Starring Rebecca Spence as Cheryl Meighan Gerachis as Casting Director Charles Malave as Skittles Player #2 Lily Emerson-Malave as Skittles Player #1 Trevor Dawkins as Skittles Guy Miroslaw Czeczot as Kyle's Friend Brian Kizer as Kyle's Friend Peg Donovan as Sophie's Manager Ron Hale as Hookup Guy Jose A. Garcia as Doorman Noah Holcom Jr. as Theatergoer Marjorie Holcomb as Theatergoer Otis Fine as Jeffrey Kate James as Paige