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 Matteo Pascale as Ethan Nunzio 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 Josh Hemphill as Frederick Larry Petersen as Marvin Brian Patrick Whitted as Tommy Corey Masklee as Wait Staff Jamie Lawrence as Jazz Pianist