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Can an independent, contemporary woman find happiness with a guy who sells pickles? Isabelle Grossman (Amy Irving) is an attractive, intelligent Jewish woman in her early 30s. She has a good job and a nice apartment on the Upper West Side, and she values her independence; she often visits her grandmother Bubbie (Reiz Bozyk), who lives on the Lower East Side and wants Isabelle to meet a nice Jewish man and settle down. Bubbie goes so far as to obtain the services of Hannah Mandelbaum (Sylvia Miles), a matchmaker who finds the "perfect" man for Isabelle: a pickle salesman named Sam Posner (Peter Riegert). Isabelle thinks Sam is a nice enough guy, but she has a hard time imagining herself spending her life with the pickle man, and she isn't sure if she wants to pursue the relationship. However, Sam is taken with Isabelle and goes out of his way to change her mind. Crossing Delancy was directed by Joan Micklin Silver, whose breakthrough film Hester Street also examined Jewish culture on the Lower East Side, albeit from the vantage point of the 1890s.