Twenty-nine-year-old bachelor Jimmy has been dating Ann for three years and feels compelled to finally ask for her hand in marriage. However when he does, the proposal comes out all wrong. Instead of accepting his offer she walks out on him. When Jimmy's grandfather dies, leaving a will stipulating that his grandson must marry by age 30 or forfeit a $100 million inheritance, he tries desperately to either win her back or find a new bride -- with his next birthday only 27 hours away.
Chris O'Donnell, Renee Zellweger, Hal Holbrook, James Cromwell, Artie Lange, Ed Asner, Marley Shelton, Sarah Silverman, Stacy Edwards, Rebecca Cross, Jennifer Esposito, Katharine Towne, Peter Ustinov, Mariah Carey, Brooke Shields, Lydell M Cheshier, Robert Kotecki, Pat Finn, Timothy Paul Perez, Romy Rosemont, Kelly Jean Peters, Jane L Powell, Jim Jackman, Christopher Carroll, Kevin Jones, Michael Deeg, Edith Fields, Michael Lee Merrins, Nicholas Pryor, Maree Cheatham, Ken Baldwin, Jenni Pulos, Niecy Nash, Marnie Alexenburg, Elizabeth Guber, Nancy O'Dell, Marnie Schneider, Brian Leonard