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Rent The Bachelor (1999)

Jimmie (Chris O'Donnell) is the ultimate bachelor - a devilishly handsome guy who loves his freedom, with plenty of swinging-single bachelor friends and a little black book filled with hundreds of women's phone numbers. But when Jimmie meets Anne (Renee Zellweger) a sweet, pretty photographer who loves her independence as much as Jimmie, he knows that he has found true love and must kiss his bachelor life goodbye. Jimmie plans to propose marriage, but manages to turn a romantic evening into a catastrophe that sends Anne running to Beijing for a photographic assignment. Rejected and broken-hearted, Jimmie learns that next day that his grandfather has died and left him $120 million. Just as he is about to start celebrating his wealth, he realises that there is a catch: He is only entitled to the money if he marries before his 33rd birthday - which is just 24 hours away!...