Autumn In New York
Will Keane (Richard Gere), an almost-fifty bachelor, is amazingly wealthy for a restaurant owner. Able to consume women faster than a fine dinner, he has left a legacy of broken hearts behind him. Always on the lookout for fresh females, he can't help but notice Charlotte Fielding (Winona Ryder) who has come to celebrate her twenty-second birthday at his over priced eating establishment.
Oddly enough, Charlotte's grandmother Dolly (Elaine Stritch), who remembers Will because he jilted her now deceased daughter (Charlotte's Mother) many years ago, introduces the two of them to each other. When Will decides to peruse Charlotte, it isn't clear whether he is trying to recapture his youth, or the memory of the woman who got away. Charlotte melts as he turns on his flattery and charm, eager to taste adulthood. But what Will doesn't understand is that he is entering into a relationship with a woman whose heart is already broken -- literally. Charlotte is dying from heart complications.
Playboy is the polite term we use in society to refer to sexually obsessed men like Will. Unwilling to commit to Charlotte or any other relationship, he sees women as mere gas station stops to fuel his desires. This is aptly demonstrated when he leaves Charlotte snacking on canapes at a friend's party while he sneaks up to the roof to engage in a quick sexual encounter with a former girlfriend.
But aside from Will's indiscretions, a couple of sexual profanities, and a fairly heavy love scene, Autumn in New York doesn't work as a movie either. In spite of the soft musical score, the romantic autumn colors, and the sentimentality of a dying heroine, it is difficult to believe the na0xEFve and inexperienced Charlotte can change thirty years of Will's predatory habits. Nor do Will's heroics to keep Charlotte alive, convince us that he won't eventually return to his sexualizing ways. The only part of the script that makes any sense at all, is when Will tells Charlotte he isn't any good for her and she should find somewhere else to spend her precious time.