Guest Stars Caroline Aaron as Shirley Maisel Joel Johnstone as Archie Cleary Brian Tarantina as Jackie David Paymer as Harry Drake Erin Darke as Mary Michael Countryman as Simon Co Starring Nunzio Pascale as Ethan Matteo Pascale as Ethan Andrew Polk as Fred Colby Minifie as Ginger Megan McGinnis as Loula Wakeema Hollis as Harriet Lilli Stein as Vivian Joanna Glushak as Mrs. O'Toole Logan Riley Bruner as Lance David Bluvband as Virgil Brandon Salerno as Truman Patrick O'Neill as Oz Jack Messina as Salvatore Melanie Minichino as Mama Sarah Schenkkan as Milly Ben Gougeon as Ed Grieg Audrey Heffernan Meyer as Dog Woman Lindsay Brill as Lady Customer Susannah Perkins as Dora Cristiano Adiutori as Papa Lucy Sorlucco as Grandmama Raleigh Shuck as Carie Ann Larry Wendorf as Louie Kelsey Carthew as Greta James DiGiacomo as Luigi Sarah Baskin as Elsa James Rich as Albert Fred Applegate as Father O'Brien John Mondin as Mel Laurie Dawn as Sister Saint Stephen Ed Jewett as Brian Tommy Beardmore as Curren Cleary Uncredited Adam Cohen as Abe's Student Dan Castiglione as Dancer Doris McCarthy as Coat Check Customer