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Hugh Hefner's Loves & Hookups

Updated June 14, 2019 363.9k views33 items

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).

  • 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....  more
    • Age: 41
    • Birthplace: Astoria, Oregon, United States of America

    #4 of 10 What Ever Happened To All Of Playboy's 'Girls Next Door'?#6 of 21 Celebrities Who Live in Las Vegas#5 of 9 11 Celebrities Who Worked At Hooters

  • 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....  more
    • Age: 36
    • Birthplace: San Diego, California, USA

    #51 of 131 The Hottest California Models of All Time#33 of 40 The Coolest Celebrities Who Play Fantasy Football#23 of 53 Celebrities Who Are Runners

  • Photo: Toglenn / Wikimedia Commons
    Hugh Hefner counted Bridget Marquardt as one of his girlfriends from 2002 - 2008.
    Bridget Christina Marquardt (née Sandmeier; born September 25, 1973) is an American television personality, model, paranormal investigator and actress, known for her role on the reality television series The Girls Next Door, which depicted her life as one of Playboy magazine publisher Hugh Hefner's girlfriends. Although not a Playboy Playmate, she has appeared in nude pictorials with her Girls Next Door co-stars and fellow Hefner girlfriends Holly Madison and Kendra Wilkinson....  more
    • Age: 48
    • Birthplace: Tillamook, Oregon, USA
  • Photo: Playboy
    Hugh Hefner was married to Kimberley Conrad from 1989 - 2010.
    Kimberley Conrad (born as Kimberley Conradt; August 6, 1962) is an American model and actress. Conrad was chosen as Playboy's Playmate of the Month in January 1988 and became Playmate of the Year 1989. Conrad was Hugh Hefner's second wife and is mother to two of his four children. In 2017 at the age of 55 Conrad duplicated her Playmate of the Year cover along with her cohorts Renee Tenison, Candace Collins, Lisa Matthews, Cathy St. George, Charlotte Kemp, and Monique St. Pierre nearly three decades on....  more
    • Age: 59
    • Birthplace: Moulton, Alabama, United States of America