A romantic comedy in which Jimmie (Chris O'Donnell), can't come to terms with leaving bachelorhood. After an unromantic attempt at proposing to his girlfriend (Renee Zellweger), she decides he isn't ready for marriage. After they have separated, his grandfather dies and his last will and testament leaves O'Donnell a $100 million inheritance, with a catch. He must be married by his thirtieth birthday. He now has 24 hours to convince his girlfriend he is ready for marriage and go to the altar.