Special Guest Stars Michael Rapaport as Leonard Guest Stars Yamaneika Saunders as Maya Laura Benanti as Jane Jones Lily Fisher as Young Ann Cole Escola as Cole Maria Bamford as Host Joe Coots as Curtis April Matthis as Millie Co Starring Thomas Place as TBD Kara Rosella as TBD Dejay Roestenberg as TBD Ben Bornstein as TBD Jo Firestone as Server Samantha MacIvor as TBD Glo Tavarez as Pat Allie Levitan as TBD Isabel Pask as Maura