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 Rita Wilson as Viola Walsh Jack Carpenter as Patric Edelstein Edward Herrmann as Lionel Deerfield Amy Sedaris as Stacie Hall Parker Posey as Vanessa Gold Jonathan Groff as Jimmy Omid Abtahi as Samir Bernard White as Kassim Manish Dayal as Dinesh Michael Nathanson as Randy Julie Boyd as Anne Vanessa Wasche as Assistant Aizzah Fatima as Furat Teal Wicks as Sara