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With his wife Elizabeth on life support after a boating accident, Hawaiian land baron, Matt King takes his daughters on a trip from Oahu to Kauai to confront the young real estate broker, who was having an affair with Elizabeth before her misfortune.
After leaving the prison, the dwarf criminal Calvin Sims joins to his moron brother Percy to steal an expensive huge diamond in a jewelry for the mobster Walken. They are chased by the police, and Calvin hides the stone in the purse of the executive Vanessa Edwards, whose husband Darryl Edwards wants to have a baby. Percy convinces Calvin to dress like a baby and be left in front of the Edwards’s house to get inside the house and retrieve the diamond. Darryl and Vanessa keep Calvin for the weekend and decide to adopt him, while Walken threatens Darryl to get the stone back.
When record store owner Rob Gordon gets dumped by his girlfriend, Laura, because he hasn’t changed since they met, he revisits his top five breakups of all time in an attempt to figure out what went wrong. As Rob seeks out his former lovers to find out why they left, he keeps up his efforts to win Laura back.
After years of helping their hubbies climb the ladder of success, three mid-life Manhattanites have been dumped for a newer, curvier model. But the trio is determined to turn their pain into gain. They come up with a cleverly devious plan to hit their exes where it really hurts – in the wallet!