Crossing Delancey (1988)

Amy Irving stars as Isabella Grossman in this enjoyable, slightly off-kilter romantic comedy from Joan Micklin Silver. A beautiful woman in her early thirties, Isabella works as the manager of New York City bookstore, putting her in contact with a wide range of stellar literary figures. Among them is Anton Maes (Jeroen Krabbe), an egotistical European poet who, smitten, offers her a job as his personal secretary. However, it becomes clear that typing and filing were not what Anton had in mind, and Isabella is soon involved with him. But her grandmother, Bubbie (Reizl Bozyk), unhappy with Isabella's unmarried status, intervenes, contracting with a matchmaker (Sylvia Miles) to introduce her to a nice Jewish man. Isabella agrees to date pickle salesman Sam Posner (Peter Riegert), and, predictably, it doesn't go too well. Naturally, things are not always as they seem, and Isabella has to rethink some of her assumptions before she can find love in this charming, old-fashioned take on romance in the 1980s.