Will Keane (Richard Gere) is a successful 48-year-old restaurateur, womanizer and recently featured in a New York magazine cover story. Charlotte Fielding (Winona Ryder) is a free-spirited, 22-year-old, celebrating her birthday in his upscale restaurant. Noticing her immediately, her grandmother, an old friend, introduces them. Will admires the hats she made and surprised to learn Charlotte is the daughter of Katy, a former girlfriend who died in a crash.
The next day, Will calls and asks Charlotte to make a hat for his date for an upcoming benefit dinner. When she delivers the hat to his apartment a few days later, he invites her to accompany him to the formal benefit under the guise that he had been stood up. There they get to know each other and later end up back at his apartment where they have sex. The next morning, while having breakfast on his terrace, Will explains that their relationship has no future. She acknowledges this, revealing she is dying from a heart condition.
The next day, they walk through the fall foliage in Central Park, and Charlotte recites lines from the poem "God's World". As they talk, she takes his watch from him, saying she'll return it when he forgets she has it. At his restaurant, they prepare a meal together for his staff, and he begins to fall in love.
With severe chest pain, Will rushes her to the hospital. The doctor explains her neuroblastoma, a rare illness in adults, has produced a tumor near her heart and she has perhaps a year to live. Asking him why his deep interest in food, Will responds, "Food is the only beautiful thing that truly nourishes."
At a Halloween party, Charlotte, dressed as Emily Dickinson, entertains children by reciting "Two Butterflies" Meanwhile, Will meets an ex (Jill Hennessy) and they end up on the roof having sex. Later, Charlotte confronts him and breaks off their relationship, which deeply affects them both.
Meanwhile, Will receives a letter from Lisa Tyler (Vera Farmiga), an illegitimate daughter he's never met. He goes to her museum, recognizes her from an old photo, but can't approach her. A few nights later he arrives home, finds her in the lobby and they talk for the first time. Pregnant, she has become sentimental about parenthood, wanting to meet her own father. She's had a dream that he's been trying to find her all these years to apologize for abandoning her. Will says quietly, "Yes I am (sorry)."
The next night, Charlotte returns home to find Will asleep in a chair. Angry at first, she tells him to leave, but he pleads for another chance. She cries as he holds her in his arms. In the morning, Charlotte recites to him from "Midnight" Later, while skating at Rockefeller Center, she suddenly collapses. At the hospital, they are told the tumor has grown and she's given only a few weeks left.
In the next days, Will searches for a specialist to perform the complicated surgery to save her. Asking his daughter for help, she finds a specialist who agrees to perform the surgery when the time comes. On Christmas morning, Charlotte wakes up and hears Will decorating. As she prepares to bring him his Christmas gift, she collapses. Rushed to the hospital, the surgeon is called. and Will, at her side, whispers to her lines from "To a young poet" before she is taken to the operating room.
Will, friends, Lisa, and Charlotte's grandmother wait during the long hours of surgery. Finally, the specialist emerges, and as he approaches it is clear that he could not save her. Back at his apartment, Will finds Charlotte's gift to him on the floor – a small box with the hat stem she designed for him. Opening it, he finds his watch she took on their first date. He stands at his window weeping, holding the box closely to his chest.
The following summer on a small boat on Central Park Lake, Will is holding his newborn grandson in his arms as his daughter Lisa looks on lovingly. Will notices a swan, and then a reflection in the water of a young woman walking over the bridge. The three drift peacefully on the lake.
Richard Gere as Will Keane
Winona Ryder as Charlotte Fielding
Anthony LaPaglia as John Volpe
Elaine Stritch as Dolores "Dolly" Talbot
Vera Farmiga as Lisa Tyler
Sherry Stringfield as Sarah Volpe
Jill Hennessy as Lynn McCale
J.K. Simmons as Dr. Tom Grandy
Sam Trammell as Simon
Mary Beth Hurt as Dr. Paul Sibley
Kali Rocha as Shannon
Steven Randazzo as Alberto
George Spielvogel III as Netto
Ranjit Chowdhry as Fakir
Audrey Quock as Eriko
Tawny Cypress as Melissa
Daniella van Graas as Model at Bar
Rachel Nichols as Model at Bar
Liza Lapira as Charlotte's birthday friend