Guest Stars Lauren Lapkus as Agent Phoebe Donnegan Rob Heaps as Dr. Josh Cohen Andrew McCarthy as James Fitzpatrick Rodney To as Agent Henry Nicholas Alexander as Darren Audrey Wasilewski as Jenny Ptolemy Slocum as Carl Irene Choi as Amy Co Starring Everleigh McDonell as Jane Boland Scarlett Abinante as Emma Boland Braxton Bjerken as Kenny Boland Danny Boyd Jr. as Harry Hill Carlos Aviles as Mick David Douglas as Pack N' Ship Customer Louisa Abernathy as Elderly Lady Dominique Morton as Kyle Brad Crowe as Angry Man