Autumn in New York (2000)

Romantic drama about an aging playboy who falls for a sweet, but terminally ill, young woman. - anonymous

Forty-eight year old Will Keane is a successful restaurateur and serial womanizer, his reputation generally preceding him. When he is introduced to twenty-two year old Charlotte Fielding by Charlotte's grandmother, Will's old friend Dolly who he has not seen in years, there is a mutual but slow to acknowledge attraction. After their first date, Will and Charlotte agree that their relationship will never progress to one of a long term standing, but for different reasons: while this is Will's somewhat standard modus operandi, Charlotte announces that she has a terminal heart condition. Charlotte's admission makes Will look at this relationship differently, he being told by his best friend John that if he is going to continue to date Charlotte that he better treat her well. Their relationship does end up being different than both expect, for Charlotte which could mean a change from her current "let me die in peace" attitude to want to fight for her life. And Will's time with Charlotte is further influenced by his encounter with a young woman named Lisa Tyler. - Huggo

A May-December romance. He's 48, on the cover of New York magazine, an upscale restaurateur, and a womanizer who rejects ideas of love. She's 22, living with her grandmother, artistic, facing a tumor that's life-threatening, which she tells him about the morning after their first night, when he tells her not to expect permanence from him. Will finds Charlotte unprecedented and unpredictable, and experiences feelings of love, but she packs him off when he's casually unfaithful. He's stung, and he's also flummoxed by the appearance of a young woman from his past. Can he convince Charlotte to take him back, and can he help her through her illness and change his irresponsible ways?