In 1966 New Jersey, Jill Rosen, a frustrated high schooler, is intrigued by an enigmatic new student known only as the Sheik. Sheik is an Italian whose primary interests are his car, Frank Sinatra, and Jill. At first she is taken aback by his forwardness, but they soon develop a relationship, much to the chagrin of their parents. Sheik gets expelled from school, and Jill is accepted at an all-girls college. After a fight, Sheik goes to Florida to work in a club lip-synching Sinatra songs. Sheik becomes dissatisfied with his Florida lifestyle and goes back to New Jersey to try to win Jill over.