Will Keane (RICHARD GERE) is a successful and suave New York restaurateur and renowned ladies man, whose age of forty-eight has neither hampered nor slowed down his efforts in either field. Charlotte Fielding (WINONA RYDER), on the other hand, is a still somewhat awkward 22-year-old woman known best for making bizarre hats. When the two meet on Charlotte's birthday through her salty grandmother, Dolores (ELAINE STRITCH), whom Will has known for quite some time, the sparks immediately fly between them, despite their differences in age.
Ever the womanizer and after an amorous evening, Will tells Charlotte that this romance won't work between them. She agrees, but for different reasons as she then informs him that she's living on borrowed time since she has a non-cancerous tumor growing inside her heart that should have killed her by now. Despite warnings from Dolores and advice from his friend and restaurant worker, John (ANTHONY LaPAGLIA), not to get involved with Charlotte, her candid disclosure has now made him fall for her.
With word from Charlotte's physician, Dr. Sibley (MARY BETH HURT), that Charlotte probably has less than a year to live, Will sets out to make her remaining time as enjoyable as possible. Yet, his involvement with several women from his past, Lynn (JILL HENNESSY), a former girlfriend and Lisa (VERA FARMIGA), the adult daughter he's never met, soon impact his and Charlotte's relationship. As Charlotte's condition continues to deteriorate and her love affair with Will hits its share of bumps in the road, they try to make things work out before time runs out for both her and them.