8 Worst Celebrity Proposal Fails

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6. Howard Stern

We must admit, we’re not to surprised to find Howard Stern on this list. He can be a bit of an oddball sometimes and it seems he was no different when he asked for his girlfriend Beth Ostrosky’s hand in marriage. The radio personality made her strip down to her birthday suit before he proposed on Valentine’s Day in 2007. He prompted her to do it by telling her that if she undressed she’d get her present, so when she finally did, he gave her a 5.2-karat diamond ring. He shared the entire story with his radio audience the next day.



5. George Clooney

This Academy Award winning actor was known for being a womanizer in Hollywood and an eternal bachelor. He once even made a $10,000 bet with Nicole Kidman and Michelle Pfeiffer that he would stay unmarried and childless until he was 40 and won that bet! That has all gone out the window since he married Amal Alamuddin in 2014 and welcomed twins on June 6th, 2017. Many people were shocked to see Clooney change his ways, and despite being known as a ladies man, Amal made him work for their relationship — especially his proposal! In an interview with Ellen DeGeneres, Clooney said he got down on one knee during a romantic, homemade dinner, but she didn’t realize he was proposing! It turned into a negotiation that went on for nearly 25 minutes before she finally said yes!