In 1966, Trenton, New Jersey, Jill Rosen, an upper middle class Jewish girl, runs into Sheik Capadilupo, an Italian-American teenager who was recently transferred to her high school after being kicked out of another. Instantly attracted to her, Sheik pursues Jill, but she rejects him when he asks her on a date. One day after school, Jill learns that she won the lead role in the school play, and finds Sheik waiting for her in the parking lot. He congratulates her on the role and convinces her to take a ride in a car borrowed from his friend, Rat. He later calls her at home, and she agrees to meet him for a date. At home, Sheik’s mother presses a suit and Sheik greases his hair in preparation for the date, while his father disapproves of Sheik’s fancy clothes and suspects he did something illegal to afford them. Outside Joey D’s, a local bar, Jill meets Sheik in the parking lot. Inside, they join Rat and his girlfriend, Joann, who reminds Jill they used to go to school together. At the end of the date, Sheik asks Jill if she will go out with him again, but Jill complains that he didn’t speak to her all night. Sheik defends himself, saying he wanted Jill to get used to him, and they kiss. The next day, Jill’s friends tease her about her new boyfriend, and Sheik interrupts one of her classes to tell Jill he’ll wait for her in the parking lot after school. As Jill practices for her play, Miss Vernon, the drama teacher, warns Jill that boyfriends provide distractions and encourages her to stay focused on acting. At Jill’s rehearsal the next day, Sheik shows up unannounced and watches from the audience. Afterward, Jill tells Sheik that she doesn’t want him to wait for her after school. Sheik throws her books on the floor and accuses Jill of acting superior. In the next days, Jill ignores Sheik’s attempts at reconciliation. On the opening night of the school play, Sheik meets Jody, one of Jill’s friends, backstage. Feeling ignored by Jill after the show, Sheik accepts Jody’s flirtatious advances and they leave together. Later, he and Jody have sex in a room behind Joey D’s. When Jill’s parents question her about Sheik, having heard about him from Miss Vernon, Jill becomes defensive and storms away. In town, Sheik and Rat spot Jill and her friend, Beth, and force the girls into their car. Sheik demands that Jill take him seriously, and they make up. One day, he convinces her to skip school and they go to the boardwalk together. That evening, at a diner, they dance to “Strangers in the Night,” a song performed by Sheik’s idol, Frank Sinatra. Later, they kiss and Sheik walks home singing. The next day, Jill and Jody talk about Jill’s plans to go to the school prom with Sheik, who later drops into Jill’s lunch period to discuss the limousine he wants to arrange for them. Mr. McManus, a teacher who has previously caught Sheik in the cafeteria without a hall pass, orders him to leave, but Sheik refuses. McManus then attacks Sheik and expels him from school. Jill goes to Joey D’s to find Sheik, but leaves after she sees him sitting with another girl. Returning home, Jill opens a letter of acceptance from Sarah Lawrence College in New York. Days later, she attends the prom with another date, but as they walk into the dance, she spots Sheik outside and he kisses her goodbye. Later, he and Rat rob a store; when the police pursue them, Rat is caught but Sheik escapes and runs to the bus station where he buys a one-way ticket to Miami, Florida. After the prom, Jill and her friends go to Joey D’s, and Jill finds Jody in the bathroom, bleeding from self-inflicted cuts to her hands. Jody complains that Jill gets everything she wants, and confesses to sleeping with Sheik. In the fall, Jill attends school at Sarah Lawrence and struggles to fit in with other students. On a double date with her friend Leslie, Jill drinks too much while her date, Steve, speaks negatively about lower class people from New Jersey. Jill responds by telling stories about Rat, then vomits at the table. After she recovers, Jill calls Sheik and tells him that she plans to come to Miami, where he is now performing at a nightclub. There, Jill watches as Sheik lip-synchs to Frank Sinatra songs for an audience of senior citizens. After they have dinner at a fancy restaurant, Jill returns with Sheik to his dingy apartment and they make love. The next day, before she heads back to school, Sheik tells Jill that he loves her, and Jill only replies that she knows. Sometime later, Jill smokes marijuana with friends and makes fun of Sheik. One day, Steve shows up at her dorm and they have sex. When Sheik is replaced by a real singer at his nightclub job, he steals a car and drives to Jill’s college for a visit. Arriving angry, he tears Jill’s room apart, awaiting her return. Meanwhile, Jill contemplates whether she will attend a school dance that evening after Steve calls to say he cannot go. That night, Jill finds Sheik in her room and they argue. Jill tells Sheik she is not in love with him and sees no future in their relationship; however, she promises that she loves him in a different way, and convinces him to go to the dance with her. At the dance, the band plays “Strangers in the Night” by request, and Sheik and Jill dance closely, staring into each other’s eyes.