Henry Graham (Walter Matthau) is a man with a problem: he has run through his entire inheritance and is completely unequipped to provide for himself. His childhood guardian, Uncle Harry (a deliciously mean-spirited James Coco), refuses to give him a dime, so Henry devises a plan with the help of his imaginative butler (George Rose) to make his money the old-fashioned way he can marry it. But he cannot see himself as a happily married man, so he comes up with an even more devious solution with a temporary loan from his uncle, Henry has six weeks to find a bride and repay the loan; otherwise he must forfeit all his property to his uncle. Henry finally meets his dearly beloved, a clumsy, painfully shy heiress Henrietta Lowell (played by the films writer/director Elaine May). The answer to his prayers - if only he can overcome the obstacles placed in his path by his uncle and Henriettas Lawyer (Jack Weston).