Guest Stars Renée Elise Goldsberry as Geneva Pine Monica Raymund as Dana Lodge Anna Camp as Caitlin D'Arcy Denis O'Hare as Judge Charles Abernathy John Benjamin Hickey as Neil Gross Edward Herrmann as Lionel Deerfield Rita Wilson as Viola Walsh Jack Carpenter as Patric Edelstein Parker Posey as Vanessa Gold Amy Sedaris as Stacie Hall Manish Dayal as Dinesh Jonathan Groff as Jimmy Omid Abtahi as Samir Michael Nathanson as Randy Bernard White as Kassim Julie Boyd as Anne Vanessa Wasche as Assistant Aizzah Fatima as Furat Teal Wicks as Sara