New York restauranteur Will Keane (Richard Gere) is an infamous verging-on-50 playboy, master of the no-commitment seduction -until he runs into an unexpected dead end when he meets Charlotte Fielding (Winona Ryder). Charlotte is half his age and twice his match, a free spirit yearning to get out and taste the excitement of adult life. Indulging his interest in Charlotte, Will expects another quick and easy romance. But nothing about Will and Charlotte's encounters are quick and easy; instead they are rife with intergenerational clashes, differing philosophies and an inexplicably urgent sense of sensuality and connection. Then just as Will attempts to escape from the relationship with his usual line of "not promising forever", Charlotte provides a surprise response: she has her own reasons to believe things can't last.