James Shannon III (Chris O'Donnell) is a man who has had dozens of girlfriends and they all break-up with him because he is unwilling to commit. But when he meets Anne Arden (Renée Zellweger), he starts to loosen up a bit, but is still a little hesitant. Even his blustery Grandad James Shannon (Sir Peter Ustinov), who is concerned of the fate of the Shannon line, is nagging him to get married and have children. So he decides to take that step, but he is so nervous, that he botches the proposal. Anne is disappointed in him. When his grandfather dies and the will is read, they discover that he has left Jimmie one hundred million dollars, but only if he gets married by 6:05 p.m. on his 30th birthday, which is the next day. Jimmie then decides to propose to Anne again, and this time does a little better, but when Anne questions his eagerness and if he truly wants to marry her, he freezes, she then gets on a plane for Greece. She gets off the plane at the last minute and goes to visit her parents. Jimmie then learns that if he doesn't get the inheritance which includes the business, a company that has a reputation of buying a business and then stripping it for all that it is worth and then laying off the employees, will buy it and lay off all of the employees. Jimmie is adivised to find someone else to marry, so he goes through his black book and proceeds to ask every girl he has dated to marry him, only some of them are still stinging from his breaking up with them, others think that it's a travesty what he is proposing, or he just continues to propose badly.—[email protected]