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James Shannon III (Chris ODonnell) is seeing his single friends get married one by one. He isnt too worried until his girlfriend Anne Arden (Renée Zellweger) catches the bouquet at his friend Marcos (Artie Langes) 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 shes gone, he finds out that his recently-deceased granddad James Shannons (Sir Peter Ustinovs) will stipulates that he gets nothing of a multi-million-dollar fortune unless hes 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.
James Shannon III (Chris ODonnell) is a man who is somewhat gullible at keeping relationships with his girlfriends. But one day, he meets Anne Arden (Renée Zellweger) and suddenly his life is changed. It is then that the night he was supposed to propose to her that he returns back to his old self again. This upsets Anne completely. Soon, his Grandad James Shannon (Sir Peter Ustinov) dies and leaves Jimmie an inheritance of one hundred million dollars with one huge condition: Jimmie must get married on his 30th birthday by no later than 6:05 p.m. Pacific time or else his San Francisco-based pool table company goes under, and/or will be sold, his bank accounts will be frozen, and employees will be laid off completely. Jimmie must now use every attempt to learn from his foolish mistakes, find his true love, get married, and save the company in one day.
Chris O'Donnell
Jimmie
Renée Zellweger
Anne
Artie Lange
Marco
Edward Asner
Gluckman
Hal Holbrook
O'Dell
James Cromwell
Priest
Marley Shelton
Natalie
Peter Ustinov
Grandad
Katharine Towne
Monique
Rebecca Cross
Stacey
Stacy Edwards
Zoe
Mariah Carey
Ilana
Sarah Silverman
Carolyn
Jennifer Esposito
Daphne
Brooke Shields
Buckley
Lydell M. Cheshier
Sanzel
Robert Kotecki
Hodgman
Pat Finn
Bolt
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