Guest Stars Jacqueline Toboni as Jo Jane Adams as Annabelle Jones Michael Chernus as Kyle Gugu Mbatha-Raw as Sophie Jake Weber as Wally Jake Johnson as Drew Co Starring Rebecca Spence as Cheryl 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 Meighan Gerachis as Casting Director Otis Fine as Jeffrey Kate James as Paige
