Isabelle Grossman works for a New York bookstore which supports authors through public readings. When author Anton Maes comes to the bookstore to give a reading, he shows an interest in Isabelle, who is enamored with the intellectual world that is very different from her traditional Jewish upbringing. Isabelle pays frequent visits to her Bubbie, Ida, who lives on the Lower East Side of Manhattan. Anxious for her granddaughter to settle down, Ida turns to the local marriage broker. Although shocked and annoyed, Isabelle allows the matchmaker to introduce her in Bubbie's kitchen to Sam Posner, who owns the nearby pickle shop. At first Isabelle is not interested in Sam, believing that he is too working-class for her. Instead, she sets her sights on Anton and the New York intelligentsia. But she also feels guilty for how rude she was to Sam, so she tries to make it up to him by setting him up with her girlfriend Marilyn. In the process, she learns that he did not hire a matchmaker out of desperation and in fact has admired Isabelle from afar for several years. She is deeply touched and begins to like him, but it seems Sam has given up on her and starts dating Marilyn. One day at a store book reading, Sam shows up, wearing a suit the matchmaker had advised him to buy. Anton arrives as well. Isabelle leaves with Sam, and later agrees to meet him the next day at her Bubbie's apartment. After work the next day, however, she is sidelined by Anton and, believing that he is romantically interested in her, goes to his apartment. She discovers instead that Anton wants the convenience of an assistant, not a true partner. Finally seeing through him, the disgusted Isabelle races to her grandmother's apartment late, finding it empty with Ida sleeping on the couch. Heartbroken, she believes she has ruined her chances with the honest and caring Sam. As she cries, Sam enters from the balcony. The two finally are united and Ida feigns confusion, but is gleeful that her plan has succeeded.
The movie received positive reviews. It currently holds an 88% rating on Rotten Tomatoes based on 24 reviews. The film is recognized by American Film Institute in these lists:
Crossing Delancey is the soundtrack album to the motion picture Crossing Delancey, released October 17, 1988. Instrumental tracks were by Paul Chihara, and songs were performed by The Roches. Suzzy Roche of the Roches played Marilyn, a friend of Isabelle, in the film. The Roches provided several songs for the soundtrack. One of the songs that was featured in the film, Nocturne, is also featured on the group's 1989 album Speak. An earlier arrangement of their cover of Come Softly to Me is featured on their album Another World.