Jimmie Shannon (Chris O'Donnell) is content living as a bachelor, valuing freedom more than life itself. As his buddies begin to pair up in marriage, Jimmie continues happily plugging away with his dating lifestyle, in no rush to find "the one."
Not expecting it, Jimmie falls in love with the adorable Anne (Renée Zellweger).. After a three-year relationship, Jimmie decides to "give in", and reluctantly proposed to Anne. Sensing his doubt and furious over his futile and lame attempt at a proposal, Anne dumps Jimmie back into the town known as "Bachelorville."
When Jimmie's grandfather (Peter Ustinov) passes away, his will states a $100 million inheritance for Jimmie, provided he marries before his thirtieth birthday, which is in less than twenty-four hours.
Seeking advice from his family attorney, Gluckman (Ed Asner) and stock broker, O'Dell (Hal Holbrook), Jimmie desperately and quickly arranges for a priest (James Cromwell) to wait in the wings while he finds a bride.
Attempting to reconcile with Anne and several other ex-girlfriends, including Buckley (Brooke Shields), a well-to-do ex-debutante; Ilana (Mariah Carey), an opera singer; Monique (Katharine Towne), a chef; Daphne (Jennifer Esposito), a cop; Zoe (Stacy Edwards), a window dresser; Carolyn (Sarah Silverman), a college student; and Stacy (Rebecca Cross) a commodities broker, Jimmie tries to discover the real meaning of love.