When he least expected it, Jimmie Shannon (O'Donnell) falls in love with Anne (Zellweger). After a three-year relationship, Jimmie reluctantly proposes to Anne, but sensing his uncertainty, Anne rejects him. Then Jimmie's grandfather dies and leaves him $100 million – on the condition Jimmie marries before he turns 30. The problem is that his 30th birthday is just 24 hours away, and he must find a bride or lose the fortune.