Matthew Shear Sam Director, Actor, Screenwriter, Executive Producer Amanda Peet Dianne Actor, Producer Alessandro Nivola David Actor Judd Hirsch Fred Actor Bob Balaban Lenny Actor Andrea Martin Helen Actor Zosia Mamet Jenny Actor Jessica Harper Toby Actor Holland Taylor Dr. Greene Actor Sheng Wang Alan Actor Charlie Alderman Producer Christopher Dodds Producer Phil Keefe Producer Emily McCann Lesser Producer David Bernon Producer Sam Slater Producer Greg Field Executive Producer Alex Field Executive Producer Greg Fields Executive Producer Conor Murphy Cinematographer Ian Blume Film Editor Christopher Bear Original Music