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Celebrity Odd Couples: Hollywood’s Most Surprising Hookups

Hollywood most surprising hook ups
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May 5 2015, Published 12:13 p.m. ET

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Hollywood most surprising hook ups
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They either seemed like an off-fitting pair or we have long forgotten that they were an item. These are Hollywood’s most odd couples.

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Jon cryer demi moore hollywoods most surprising hookups

Jon Cryer, 50, once romanced Demi Moore, 52. Sadly, he says his “inaugural Hollywood romance” ended when he stopped by Demi’s place one night, only to have her housekeeper reveal that she was “out with her boyfriend.”

Brad pitt christina applegate hollywood hook ups
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Christina Applegate, 43, and Brad Pitt, 51, walked the red carpet together in 1989 — but never made it past the first date! “We went to the MTV Movie Awards, and I ditched him,” confesses Christina. “I left with somebody else!”

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Kelly preston george clooney hollywoods most surprising hookups
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Kelly Preston, 52, and George Clooney, 53, dated for two years beginning in 1987, sharing a home in Hollywood and custody of a potbellied pig named Max, which George kept after the couple split.

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Cher tom cruise hollywoods most surprising hookups
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It was only a brief fling in 1986, but Cher, 68, still considers Tom Cruise, 52, to be “in the top five” of her long list of lovers. “It could have been a great big romance, because I was crazy for him,” says the singer.

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