The Rachel Papers (1989)

Synopsis
A teen sex comedy derived from the arch debut novel of author Martin Amis by debut director Damian Harris (son of actor Richard Harris). Dexter Fletcher stars as Charles Highway, a 19-year-old computer nerd in London who has created a program that will allegedly guide him through the process of seducing a girl. Charles is determined to win over a beautiful, older woman before he enters Oxford University as a freshman. Then he meets 20-year-old American girl Rachel Noyce (Ione Skye), who unfortunately has a boyfriend named DeForest (James Spader). Since Rachel is a bit of a free-spirited swinger, however, Charles might have a chance, but her complexity dooms his ill-conceived "Master of Seduction" computer program. ~ Karl Williams, All Movie Guide