Hugh Hefner's Loves & Hookups

All of Hugh Hefner's past and present girlfriends and wives. Hefner dated tons of women, most of them 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 "tapes" with other high-profile men. Kendra Wilkinson, for example, is high on the list of such celeb tapes and is no stranger to the attention. As of now, Hef himself has not been in the middle of a celebrity 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 was still his wife upon his passing in 2017. Other notable Hugh Hefner partners include Holly Madison, Shannon Tweed, and Bridget Marquardt. 

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

  • Crystal Harris
    Photo: Toglenn / Wikimedia Commons
    Hugh Hefner dated Crystal Harris on-and-off since 2008. The couple tied the knot in 2012.
    Crystal Hefner (née Harris) (born April 29, 1986) is an American model and television personality. She was the Playboy Playmate of the Month for December 2009, and is the widow and the third wife of Playboy publisher Hugh Hefner from December 31, 2012, until his death on September 27, 2017.
    • Age: 36
    • Birthplace: Lake Havasu City, Arizona, USA
  • Anna Sophia Berglund
    Photo: Toglenn / Wikimedia Commons
    Hugh Hefner was involved with Anna Sophia Berglund in 2011.
    Anna Sophia Berglund is a film and television actress.
    • Age: 36
    • Birthplace: San Pedro, Los Angeles, California, United States of America
  • Jenna Bentley

    Hugh Hefner was reportedly linking up with Jenna Bentley in 2009.

  • Kristina Shannon
    Photo: Metaweb (FB) / Fair use
    Hugh Hefner was romantically involved with Kristina Shannon from 2008 - 2010.
    Kristina Shannon is a film actress.
    • Age: 33
    • Birthplace: Ann Arbor, Michigan, USA
  • Holly Madison
    Photo: / Wikimedia Commons
    Holly Madison was one of Hugh Hefner's girlfriends from 2001 - 2008.
    Holly Madison (born December 23, 1979) is a model, showgirl, television personality and New York Times best-selling author. Madison is known for her role in the E! reality television show The Girls Next Door and for her own series, Holly's World. In July 2015, Madison released her first book and memoir, Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny. In May 2016, she released her second book, The Vegas Diaries: Romance, Rolling the Dice, and the Road to Reinvention detailing her career and dating life in Las Vegas.
    • Age: 43
    • Birthplace: Astoria, Oregon, United States of America
  • Kendra Wilkinson
    Photo: Eva Rinaldi / Wikimedia Commons
    Kendra Wilkinson was in a relationship with Hugh Hefner from 2004 - 2008.
    Kendra Leigh Baskett (née Wilkinson; born June 12, 1985) is an American television personality, businesswoman, glamour model, and author. She is known for being one of Hugh Hefner's girlfriends and for her role on the E! reality television series The Girls Next Door, on which her life in the Playboy Mansion was documented. Although not a Playboy Playmate, she has appeared in three nude pictorials with her Girls Next Door co-stars and fellow Hefner girlfriends Holly Madison and Bridget Marquardt. Her first reality series, Kendra, debuted in June 2009 and ended in November 2011.
    • Age: 37
    • Birthplace: San Diego, California, USA