James Shannon III (Chris O'Donnell) is seeing his single friends get married one by one. He isn't too worried until his girlfriend Anne Arden (Renée Zellweger) catches the bouquet at his friend Marco's (Artie Lange's) wedding. Suddenly, his wild mustang days are numbered. He finally decides to propose to her, but he sticks his foot in his mouth and botches the proposal. Being insulted by the defeatist proposal, Anne leaves town on an assignment. After she's gone, he finds out that his recently-deceased granddad James Shannon's (Sir Peter Ustinov's) will stipulates that he gets nothing of a multi-million-dollar fortune unless he's married by 6:05 p.m. on his 30th birthday: tomorrow. Not being able to find Anne, Jimmie begins backtracking through his past girlfriends to find a wife.