Will Keane (Richard Gere) is a womanizing restaurateur on the cover of a magazine. Charlotte Fielding (Winona Ryder) has her 22th birthday party at his restaurant. She makes weird little hats. Her grandmother (Elaine Stritch) knows him as an old friend of her mom. He starts flirting with her and maneuvers her to a date. After their first night together, he tells her that he can offer her nothing, and she tells him that she has a terminal heart tumor. Meanwhile there is a mystery woman Lisa Tyler (Vera Farmiga) around.

There is a high ick factor especially since the movie hints at him and her mother having a thing in the past. She's playing a giggly little girl. She's literally giggling about him dancing with her mother. He's the weaselly Don Juan type. She's so young that she can't see that he was just trying to seduce her that first time around. She's so clueless that she's shocked by her mother's past with him. It's not romantic. It's just sleazy. Next to Gere, Winona Ryder is like a fawning teenager. And why do they have to keep talking about her mother? I understand that there is a May to December romance that gets turned upside down. It's not as poetic as the movie supposes. The chemistry is all wrong. If she doesn't start off as terminal, then it might make the movie more poetic. The dialog is fairly weak and there is limited tension in the story. I don't know what drives the movie if we rule out happily ever after right off the bat.