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