Guest Stars Renée Elise Goldsberry as Geneva Pine Anna Camp as Caitlin D'Arcy Monica Raymund as Dana Lodge 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 Bernard White as Kassim Michael Nathanson as Randy Julie Boyd as Anne Vanessa Wasche as Assistant Aizzah Fatima as Furat Teal Wicks as Sara