8 Most Ridiculously Mismatched Couples

One of the most awkwardly mismatched couples has definitely got to be Hugh Hefner and Crystal Harris, and age has a lot to do with it. She was once just a Playmate until Hugh popped the question and she became his wife. Crystal is Hugh’s third much younger spouse – she is only 27 and he is 87, which makes him old enough to be her grandfather.

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This leaves many wondering if she married him because she is actually in love with him or because she is more in love with the money and fame. Hefner is founder and CEO of Playboy enterprises with a mansion valued at $54 million. In fact, a couple of years ago, the value of the Los Angeles mansion was the subject of a heated court case.

Hefner, who owned 69.5% of the company shares, tried to undervalue the company’s assets as he made a pitch to take it private. He claimed that the 29 room manor was only worth $1.2 million!! Hmmm.. I wonder if the L.A. estate has anything to do with why Crystal married the Playboy founder…