Failed hockey player-turned-golf whiz Happy Gilmore -- whose unconventional approach and antics on the grass courts the ire of rival Shooter McGavin -- is determined to win a PGA tournament so he can save his granny's house with the prize money. Meanwhile, an attractive tour publicist tries to soften Happy's image.
A plastic surgeon, romancing a much younger schoolteacher, enlists his loyal assistant to pretend to be his soon to be ex-wife, in order to cover up a careless lie. When more lies backfire, the assistant's kids become involved, and everyone heads off for a weekend in Hawaii that will change all their lives.
Lenny has relocated his family back to the small town where he and his friends grew up. This time around, the grown ups are the ones learning lessons from their kids on a day notoriously full of surprises—the last day of school.