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The Many Loves Of Hugh Hefner

Lifelong ladies man Hugh Hefner finally married Crystal Harris on New Year's Eve. In honor of their recent nuptials, let's take a look at the other ladies in Hef's past.

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Playboy founder Hugh Hefner has had countless lovers over the years — some more notable than others. Here's a chronological history of the wives, girlfriends, and Bunnies who found themselves in his bed. Because Hef has never been a one-woman man, there's a lot of overlap.

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Holly Madison (2003-2008)

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Another one of the Girls Next Door, Holly broke up with Hef because he wouldn't put a ring on it. She has since moved on to other reality TV endeavors.

Kendra Wilkinson (2004-2009)

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Kendra lasted longer than the other Girls Next Door, but she and Hugh eventually parted ways. Now going by her married name Kendra Baskett, her current series is Kendra on Top.

Kristina and Karissa Shannon (2009-2010)

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Along with Crystal Harris, Kristina and Karissa were Hef's rebounds after his break-up with Holly. They also appeared on The Girls Next Door.

Crystal Harris (2009-2011, 2012-)

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Crystal and Hugh have been on-again, off-again, but now they're officially married. Their New Year's Eve wedding was held at the Playboy Mansion.