- Directors: Nancy Meyers
- Producers: Nancy Meyers
- Writers: Nancy Meyers
- Genres: Comedy, Romance
- Actors: Jack Nicholson, Diane Keaton, Keanu Reeves, Amanda Peet
Harry Sanborn (Jack Nicholson) is a wealthy New York music mogul who has had a habit of dating women under 30 for 40 years. When he and his latest conquest, Marin Klein (Amanda Peet), drive to her mother’s Hamptons beach house on the coast, his life turns upside down.
Expecting to be alone, Harry and Marin are surprised by Marin’s mother, successful playwright Erica Barry (Diane Keaton), and her sister Zoe (Frances McDormand). After an awkward dinner, the night turns disastrous when â€” during foreplay with Marin â€” Harry has a heart attack and is rushed to a hospital. The handsome young doctor, Julian Mercer (Keanu Reeves), tells Harry to stay in the area for a few days, and so Harry ends up staying with Erica. Their differing personalities initially make for awkward living arrangements (seeing her naked), until the two begin to get to know each other.
Soon, the two have fallen in love, they live very different lifestyles â€” Erica’s determination to be single and independent, and Harry’s constant desire for new women and experiences â€” combined with the fact that Harry is dating Marin and Julian has fallen for Erica, leave the two struggling to deal with their current relationships with others, but also work on their own. Marin soon breaks up with Harry after she suspects that he’s in love with her mother. The break up is not out of anger, but rather she wants her mother to be able to have a relationship with him and for her own life to move on. Harry and Erica spend more time together and the relationship they have with each other gets even more serious. Harry’s improving health means that he no longer has to stay with Erica, and in a very awkward decision, he heads home.
While Harry is gazing over the river Seine in the Paris night saying “look who gets to be the girl” as it starts to snow, Erica pulls up in a taxi. She gets out and explains to Harry that Julian figured that they both still loved each other. Harry says “I’m 63 years old and for the first time in love”. Harry and Erica kiss; the movie resumes about one year and a half later at another restaurant in New York. Erica and Harry are eating out with Marin and her new husband with their year old child.