Jimmie Shannon (Chris O’Donnell) is happily single and in no rush to find “the one.” When he least expects it, Jimmie crosses paths with the adorable Anne (Renee Zellweger) and falls in love. After a three-year relationship, Jimmie feels the pressures of commitment and decides to “give in”, reluctantly proposing to Anne. Sensing his uncertainty and angry over his botched and lame attempt at a proposal, Anne dumps Jimmie. Shortly thereafter, Jimmie’s grandfather (Peter Ustinov) passes away and, determined to get Jimmie married and carry on the family line, wills a $100 million inheritance to his grandson, on the condition he marries by nightfall on his thirtieth birthday, which is less than twenty-four hours away — the race is on for The Bachelor.

Jimmie hastily arranges for a priest (James Cromwell) to wait in the wings while he finds a bride. He tries to reconcile with Anne and several other ex-girlfriends, including a well-to-do ex-debutante (Brooke Shields), an opera singer (Mariah Carey), a chef (Katharine Towne), a cop(Jennifer Esposito), a window dresser (Stacy Edwards), a college student (Sarah Silverman), and a commodities broker (Rebecca Cross). Through these hilarious antics, Jimmie can’t help but discover the true meaning of love.