Sutton Foster Liza Miller Actor Debi Mazar Maggie Actor Miriam Shor Diana Trout Actor Nico Tortorella Josh Actor Peter Hermann Charles Actor Hilary Duff Kelsey Peters Actor Molly Bernard Lauren Actor Kate Blumberg Winnie Guest Star Charles Michael Davis Zane Guest Star Campbell Dunsmore Jessica Guest Star Phoebe Dynevor Clare Guest Star Katie Lee Katie Lee Guest Star Aasif Mandvi Jay Mallick Guest Star Jaime Schwarz Michiko Guest Star Michael Urie Redmond Guest Star Jennifer Westfeldt Pauline Guest Star Mather Zickel Richard Guest Star Darren Star Executive Producer, Director