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Harry Sanborn (Jack Nicholson) is a legendary womanizer. Now 60-something, he's notorius for dating only much-younger women. His current squeeze, Marin (Amanda Peet), takes Harry to her mom's Hamptons beach house to consummate the relationship.

Turns out mom, succesful (if neurotic) divorced playwright Erica Barry (Diane Keaton), and her sister, feminist professor Zoe (Frances McDormand), are there as well. Harry has a mild heart attack and his doctor, Julian Mercer (Keannu Reeves), say's Harry can't travel, leading to changing ideas, beds, and relationships.