Harry Sanborn (Jack Nicholson) is a perennial bachelor who only dates women under the age of 30. On what was to have been a romantic weekend with his latest infatuation, Marin (Amanda Peet), at her mother’s beach house, Harry develops chest pains. Marin’s mother, Erica (Diane Keaton), a successful, divorced playwright, reluctantly agrees to help nurse him back to health. Alone together, Harry is surprised to find himself drawn to Erica for all the right reasons. And despite her initial protestations about Harry, Erica finds herself rediscovering love. Romantic complications arise when Erica is pursued by Harry’s charming young doctor, Julian Mercer (Keanu Reeves).