Producer and writer John Hughes effectively remade Pretty in Pink here (even hiring the same director, Howard Deutch), only pausing to swap Molly Ringwald with Eric Stoltz in the role of the teen who can't choose between the neighbourhood beauty and the less glamorous (but infinitely nicer) best friend as his love interest. This is gentler and more subtle than Pretty in Pink, with Back to the Future's Lea Thompson in one of her best roles as the spoilt girl that garage attendant Stoltz falls for, and Mary Stuart Masterson delightful as the tomboy who secretly harbours deeper feelings for her male friend. Stoltz makes an effective leading man, giving a touching performance in what is a genuinely charming film.

Keith Nelson, an artsy high school outcast, tries to land a date with popular girl Amanda Jones with some help from his tomboy best friend, Watts. However, Watts realizes she likes Keith as more than just a friend and tries to convince him to stop pursuing Amanda. Matters are further complicated when Keith's invitation draws the ire of Amanda's rich yet snobby ex-boyfriend, Hardy Jenns, who makes plans to get even.