Jimmie Shannon values his freedom more than life itself. As his male peers, even his best buddy, Marco, begin to hook up in marriage, Jimmie continues happily plugging away with his dating lifestyle, in no rush to find "the one." When he least expects it, Jimmie crosses paths with the adorable Anne and falls in love. After a three-year relationship, Jimmie feels the pressures of commitment and decides to "give in", reluctantly proposing to Anne at the most romantic of restaurants. Sensing his uncertainty and angry over his botched and lame attempt at a proposal, Anne dumps Jimmie back into the town known as "Bachelorville." Shortly thereafter, Jimmie's grandfather passes away and wills a $100 million inheritance to his grandson, on the condition he marries before his thirtieth birthday, which is less than twenty-four hours away...