couples 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
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Hugh Hefner dated Crystal Harris on-and-off since 2008. The couple tied the knot in 2012.

Age: 30

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

Profession: Model, Singer, TV Personality

Credits: The Girls Next Door

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

Age: 29

Birthplace: San Pedro, Los Angeles, USA, California

Profession: Model, Actor

Credits: Fired Up!

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3

Jenna Bentley


Jenna Bentley is listed (or ranked) 3 on the list Hugh Hefner's Loves & Hookups
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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
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Hugh Hefner was romantically involved with Kristina Shannon from 2008 - 2010.

Age: 27

Birthplace: Michigan, USA, Ann Arbor

Profession: Model, Actor

Credits: Somewhere, The Girls Next Door

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