Jimmie (Chris O'Donnell) and Anne (Renée Zellweger) are in a committed relationship, but the pressure is mounting on Jimmie to propose. Rather than lose Anne, Jimmie decides to ask for her hand in marriage. But when he delivers a lackluster speech to her, Anne turns him down. Jimmie soon finds out that he has one day to find a woman and marry her; otherwise he will lose out on his hefty inheritance. What ensues is a crazed search through Jimmie's past to find a suitable bride.