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