Jimmie Shannon (CHRIS O'DONNELL) is a self-proclaimed bachelor who loves the freedom of not being tied down. Although he and his photographer girlfriend, Anne (RENEE ZELLWEGER), get along just fine, neither seem ready or willing to move on to the next big step of their relationship.
Yet when his friends, including best buddy and coworker, Marco (ARTIE LANG), gets hitched, Jimmie starts to feel the pressure. Arranging a romantic dinner at an establishment known for inducing marriage proposals, Jimmie reluctantly and awkwardly pops the question to Anne. She sees that his heart isn't really into it, however, and turns him down.
As Anne returns home to complain to her roommate sister, Natalie (MARLEY SHELTON), Jimmie gets some mixed news. For one, he learns that his grandfather (PETER USTINOV) has passed away, but has left Jimmie the $100 million balance of his estate in his will. The catch, however, is that Jimmie has to be married by just after 6:00 p.m. on the day of his thirtieth birthday, which just happens to be the following day.
With the prompting of Marco, family attorney Gluckman (EDWARD ASNER), and stock broker O'Dell (HAL HOLBROOK) who collectively inform him that the family's billiards business will be sold due to provisions in the will if he doesn't get married, Jimmie halfheartedly asks Anne again for her hand in marriage. Nevertheless, she turns him down once more and reportedly heads off for a three-week assignment in Athens.
Thus, and with less than twenty-four hours to go and realizing that the money and his company are at stake, Jimmie starts asking his former girlfriends -- including ex-debutante Buckley (BROOKE SHIELDS), opera singer Ilana (MARIAH CAREY), commodities broker Stacy (REBECCA CROSS), and tough cop Daphne (JENNIFER ESPOSITO), among others -- to marry him and even has a priest (JAMES CROMWELL) standing by just in case any of them might agree to the arrangement.
With time running out, things looking bleak and Marco, Gluckman, and O'Dell willing to do anything to make sure he gets married, Jimmie finds his views on marriage changing and hopes he'll have another chance with Anne.