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Hugh Hefner and Crystal Harris
It may seem like an obvious one, but Hugh Hefner is surely the king of punching above his weight. The 87-year-old Playboy founder has been romantically involved with a number of his Playboy playmates, but decided to marry 27-year-old Crystal Harris in 2012 after she had spent some time as his 'number one girlfriend'.
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Date 2 mins ago, Duration 1:36, Views 0