Autumn in New York (2000)

Synopsis
An man gets an unexpected lesson in love and life from a much younger woman in this romantic drama. Will Keane (Richard Gere) is a wealthy 50-year-old restaurant tycoon who has a knack for wooing beautiful women, but is unable to commit to a lasting relationship. On day Will meets a beautiful woman in her early-20s named Charlotte Fielding (Winona Ryder); he turns on the charm in an effort to impress her, and soon the two are having an affair. But what Will thought would be a brief, casual fling proves to have far deeper repercussions when he learns that Charlotte is suffering from a serious illness and does not have long to live. Autumn in New York was directed by actress-turned-filmmaker Joan Chen and co-stars Anthony LaPaglia, Elaine Stritch, and Jillian Hennessy. ~ Mark Deming, All Movie Guide