Upper-middle-class Jewish girl Jill Rosen, who is bound for Sarah Lawrence College, meets a blue collar Italian boy nicknamed the Sheik, who aspires to follow in Frank Sinatra's footsteps.
In the moments before they undress, their conversation turns to his odd nickname, which he had not explained to Jill when they dated in high school.
He steals a car and makes the long drive from Miami to Sarah Lawrence in New York, propelled by the romantic notion of reuniting with Jill.
The act of consummating her desire for Sheik has led her to realize that she does not love him, having moved past the point of romantic and sexual wonder.
When Sheik arrives at Sarah Lawrence and does not find Jill, he violently trashes her room and waits for her return.
In the midst of the dance, Sheik and Jill submit a request for the rock band to perform "Strangers in the Night", the Sinatra hit that had been a key part of their high school romance in New Jersey.
[1] Rosanna Arquette reflected on the role shortly after the film's theatrical release: "I went to high school for a while, but my experiences were shitty.
Specifically, "it may take twenty minutes for an audience to realize that [the Sheik] actually attends high school and isn't a dropout hanging around.
For Sayles this is lighter fare than what he usually tackles, but he fights through all the teenage clichés to give his own spin on this romance, the significance of social-class differences, how it is to finally grow up by listening to your heart and to change with the times.