Guest Stars Charles Michael Davis as Zane Anders Phoebe Dynevor as Clare O'Brien Michael Urie as Redmond Jennifer Westfeldt as Pauline Turner Brooks Mather Zickel as Richard Aasif Mandvi as Jay Mallick Kate Blumberg as Winnie Co Starring Katie Lee as Herself Campbell Dunsmore as Jessica Jaime Schwarz as Michiko Aoki