Sophisticated, single New Yorker Izzy Grossman (Amy Irving) has left behind the “old ways” of her Jewish heritage. Working at a Manhattan bookshop organizing prestigious author readings, she revels in the society of the literati. Her Upper West Side life clashes with her Lower East Side upbringing, however, when her grandmother (Reizl Bozyk) enlists a matchmaker to set her up with the man who runs the pickle shop, Sam Posner (Peter Riegert). Crossing Delancey not only portrays the tension between modernity and tradition, but also paints a rich picture of New York’s diverse splendor in the late 1980s.