Harry Sanborn (Jack Nicholson) is a wealthy New York music mogul who has had a 40-year habit of dating women under 30, including his latest conquest, Marin Klein (Amanda Peet). Harry finds younger women very uncomplicated and extremely satisfying. Harry tells the girls that women above a certain age do not date him, so it is not his fault.The two drive to her mother's Hamptons beach house expecting to be alone, but are surprised by Marin's mother, successful playwright Erica Barry (Diane Keaton), along with her sister Zoe (Frances McDormand).
Harry was in the kitchen chilling the champagne when Erica and Zoe walked in from outside and assumed that Harry is a burglar. Only when Marin comes into the kitchen, is when the situation is clarified, and Erica cancels her 911 call.Harry offers to leave, but Zoe says that they are all adults, and there is no reason why all four could not stay for the weekend. Together they go shopping to a local supermarket. Erica learns that Harry owns a records company called Drive-By Records which produces hip-hop albums. Erica says she hates hip-hop as she finds it violent and misogynist. Harry already regrets agreeing to stay over.Harry and Marin met at a wine auction at Christie's.Harry and Marin had restrained from having sex and this weekend was when they were both looking forward to having it. The dinner is awkward as it is revealed that Harry has never been married and Zoe remembers an article on Harry in the New York Magazine. The article was titled "the escape artist". Harry was once engaged to Diane Sawyer, which impresses Erica.
Zoe is amazed that Harry is 63 and never married. If he was a woman, he would be consider cursed, and yet as a man he is celebrated as elusive. The whole over 50 dating scene only looks like older men dating women as young as Marin.The night turns disastrous when, during foreplay with Marin, Harry has a heart attack and is rushed to a hospital.The doctor, Julian Mercer (Keanu Reeves), tells Harry to stay nearby for a few days, so Harry ends up staying with Erica. Their personalities clash and make for awkward living arrangements at first until they get to know each other. The fact that Harry is dating her daughter, and that Julian has fallen for Erica leave the two struggling to deal with relationships.Marin tells her mother that she will break up with Harry, but he ends things first. He and Erica spend more time together and eventually consummate their relationship. Harry discovers that his improving health means that he no longer has to stay with Erica, so he heads home. He and Erica share an awkward goodbye, as despite their strong feelings, Harry is clearly hesitant to enter into a relationship.Marin receives news that her father, Erica's ex-husband, whom she still allows to direct her plays, is getting remarried. Although Erica is unaffected by the news, Marin is devastated and pressures her mother into accompanying her to a family dinner. Erica is the life of the party until she sees Harry at another table with another woman. An argument follows and Erica confesses that she is in love with him, but he does not seem to reciprocate, so she ends things between them and leaves. Harry suffers from what he believes is another heart attack, but he is told by the young ER physician, Dr. Martinez (Rachel Ticotin), who treats him like her father, that it was only a panic attack.Devastated, Erica returns home where she cries almost nonstop for several weeks. She pours her heartbreak into a new play about a woman who falls in love with her daughter's boyfriend, titling it "A Woman to Love," a phrase Harry had used to describe Erica. Harry hears about it and rushes to the NYC theater where it is being rehearsed. Despite her denials, it is quickly obvious that she has used the most personal details of their affair in the play.
When Harry tells her he still cares about her, she rebuffs him. After learning his character dies in the play, he suffers another panic attack. At the hospital, he is told he needs to reduce stress, and he relocates temporarily to the Bahamas.Six months pass. Erica's play is a huge success. Harry pays Marin a visit to apologize for anything he ever did to hurt her. She replies that he was nothing but nice to her and happily tells him that she is pregnant and has a new husband. Harry expresses a desire to see Erica. Marin tells him that her mother is in Paris to celebrate her birthday. Harry decides to surprise Erica.Remembering how they had once planned to spend their birthdays together there, he shows up at the Parisian restaurant where she is seated at a table. Harry explains that over the past six months he reached out to all of the women he ever had affairs with, and even though repeatedly rebuffed at first, finally broke through. They all had identical harsh stories that helped him learn how "I arrived at being me." He tells Erica that his trip to find her was the last and the farthest. Julian appears. All along, Erica has been waiting at the restaurant for Julian, whom she is now dating.Harry and Erica get along well during the dinner, but they part outside the restaurant. While he is gazing in heartache over the river Seine, Erica pulls up in a taxi. She explains that Julian figured out what was happening between them and decided to step aside to let Erica be with Harry. Harry explains that his search the last six months has made him realize he truly loves Erica. He tells her that at age 63, he is in love for the first time in his life, and they embrace. Harry and Erica kiss.A year later, at a New York restaurant, Erica and Harry, now married, are out with Marin and her husband and new baby, as one big happy family.
Storyline
Harry Sanborn is an aged music industry exec with a fondness for younger women like Marin, his latest trophy girlfriend. Things get a little awkward when Harry suffers a heart attack at the home of Marin's mother Erica. Left in the care of Erica and his doctor, a love triangle starts to take shape. — Keanuette Sixty-three year old Harry has a reputation for dating girls a third his age. Taking Marin, his latest belle, back to her beach house for the weekend he is taken aback when her mother Erica unexpectedly turns up. Suffering a heart attack while romancing Marin, Harry finds himself housebound with Erica his nurse and only companion. As they grudgingly get to know each other something starts to stir, though as the hospital doctor who treated him has taken a shine to Erica, Harry could have serious competition. — J-26