Models Hugh Hefner's Loves & Hookups  

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All of Hugh Hefner's past and present girlfriends and wives. The ultimate playboy, Hefner has dated tons of women, most of them Playboy bunnies who he discovered. This long list of lovers and exes covers an entire lifespan yet the women seem to always be young. One of many famous celebs who married much younger women, Hugh Hefner has only been married a couple times but he's dated continuously. Not that it's unexpected, but some of the gorgeous women on Hugh's arm have been caught on celebrity sex tapes with other high-profile men. Kendra Wilkinson, for example, is high on the list of celeb sex tapes and is no stranger to the attention. As of now, Heff himself has not been in the middle of a celebrity sex tape scandal, but who knows what the wily old man will get up to next? Here are all the playmates Hefner's been official with (who knows how many are "unofficial").

At age 86, Hugh Hefner married 26-year-old model Crystal Harris, who is still his current wife. Other notable Hugh Hefner partners include Holly Madison, Shannon Tweed, and Bridget Marquardt. 

On September 27, 2017, Hugh Hefner died at 91 of natural causes. 

Check out this list of Hugh Hefner girlfriends and Hugh Hefner's wife (or Hugh Hefner wives).

Crystal Harris is listed (or ranked) 1 on the list Hugh Hefner's Loves & Hookups
Photo: via Imgur
Hugh Hefner dated Crystal Harris on-and-off since 2008. The couple tied the knot in 2012.

Crystal Harris is an American model, and "singer". She was the Playboy Playmate of the Month for December 2009. On December 24, 2010, she became engaged to Hugh Hefner (then age 84), to become his third wife. Harris broke off the engagement on June 14, 2011, just five days before their planned wedding. Harris' parents were British entertainers, who were working at the England-themed amusement park in Lake Havsu City, Arizona when she was born. After Crystal's birth they returned to England, before returning for good to the United States and settling in San Diego, California, where she and her two elder sisters grew up. Harris was first exposed to the entertainment industry through her late ...more on Wikipedia

Age: 31

Birthplace: Lake Havasu City, Arizona, United States of America

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Anna Sophia Berglund is listed (or ranked) 2 on the list Hugh Hefner's Loves & Hookups
Photo: via Reddit
Hugh Hefner was involved with Anna Sophia Berglund in 2011.

Anna Sophia Berglund is a film and television actress. ...more on Wikipedia

Age: 31

Birthplace: San Pedro, Los Angeles, California, United States of America

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Jenna Bentley

Jenna Bentley is listed (or ranked) 3 on the list Hugh Hefner's Loves & Hookups
Photo: via Twitter
Hugh Hefner was reportedly hooking up with Jenna Bentley in 2009.

Kristina Shannon is listed (or ranked) 4 on the list Hugh Hefner's Loves & Hookups
Photo: via Wikimedia
Hugh Hefner was romantically involved with Kristina Shannon from 2008 - 2010.

Kristina Shannon is a film actress. ...more on Wikipedia

Age: 28

Birthplace: Ann Arbor, Michigan, United States of America

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