The Bachelor

When a young, wild and carefree man inherits a $100 million fortune from his grandfather he is quite excited, but there is a condition to meet. Young Jimmie Shannon (Chris O'Donnell) must be married by 6:05 PM on his 30th birthday, which is only one day after he discovers the inheritance. When he tries to propose to his girlfriend of three years Anne (Renee Zellweger), she can see right through it, so he takes a few friends (Artie Lange, Ed Asner and Hal Holbrook) and a priest (James Cromwell) and tries to make good on the condition with several ex-girlfriends. When none of those work out he becomes desperate and must figure out whether he wants to be married for the money or for love and a family, and whether or not he can win the heart of Anne in the end.