Guest Stars Brian Tarantina as Jackie Will Brill as Noah Weissman Justine Lupe as Astrid Weissman Erin Darke as Mary David Aaron Baker as Charles Connelly Mary Testa as Drina Romanoff Nate Corddry as Randall Michael Nathanson as Lew Fogelman Byron Jennings as Irving Connie Ray as Mrs. Winters Co Starring Nunzio Pascale as Ethan Matteo Pascale as Ethan Matilda Szydagis as Zelda Holly Curran as Penny Pann Wakeema Hollis as Harriet Lilli Stein as Vivian David Bluvband as Virgil Patrick O'Neill as Oz Caitlin McGee as Vonnie Larry Petersen as Marvin Josh Hemphill as Frederick Brian Patrick Whitted as Tommy Corey Masklee as Wait Staff Jamie Lawrence as Jazz Pianist