At 63, Harry Sanborn (Jack Nicholson) has everything every guy wants: Money, power and hordes of women under 30 throwing themselves at him. His current flame is Marin (Amanda Peet), whose mom, famous Broadway playwright Erica Barry (Diane Keaton), has a sweet beach house in the Hamptons. The May-December couple has a romantic weekend in mind when they take the Long Island Expressway out to mom's fancy shack, but their plans change when her high-strung mom and feminist aunt Zoe (Frances McDormand) turn up there, too, catching Harry raiding the fridge in his briefs. After such inauspicious beginnings, it's not surprising that Harry and Erica are at each other's throats, and shortly thereafter, the stress gets to Harry and his ticker gives out. After consulting with hottie local doc Julian Mercer (Keanu Reeves), the crew decides that Harry, unable to travel, will have to recuperate in the Hamptons, and Erica gets stuck taking care of the reluctant patient in her home while trying to write her new play. It all gets complicated when Erica and Harry start to fall for each other, Marin breaks it off with Harry, and Julian gets a yen to play doctor with Erica.