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Hugh Hefner's Girlfriends

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Hugh Hefner's Girlfriends

The founder and editor in chief of the world-famous Playboy Magazine, Hugh Hefner, requires little introduction. And, with his recent demise on September 27, 2017, at the age of 91, it can be rightly touted as an end of an era for both the leading American publishing house as well as the revolution that both stirred and transformed print media like never before.

A sneak peek into Hugh Hefner’s early life

Born as Hugh Marston Hefner in his hometown Chicago, Illinois on April 9, 1926, during the prohibition era, Hugh was the first child of Glenn Lucius Hefner and Grace Caroline. Hugh graduated from the University of Illinois with a Bachelor of Arts in Psychology. And although he went on to pursue another graduate course in Sociology at the North Western University, Hugh Hefner soon dropped out and took up a copywriter position at Esquire.

After quitting his first job, he decided to raise a handsome sum of money from investors and bank loans to launch the first ever issue of the Playboy that was originally slated to be called the Stag Party. The magazine was finally introduced in December 1953 with Marilyn Monroe’s famous nude picture as the cover page. The Playboy met with a hugely successful first run and went on to sell over 50,000 copies.

Hugh Hefner died at his Holmby Hills home in California surrounded by his family and friends. A 91-year-old man, Hugh suffered a series of medical conditions and died from a cardiac arrest, sepsis, respiratory failure and also an E.coli infection. His remains lie at a $75,000 crypt at the Westwood Memorial Park beside Marilyn Monroe’s. Acknowledging his great adoration for the legendary Hollywood star, Hefner once said “Spending eternity next to Marilyn is an opportunity too sweet to pass”.

Describing his family as ‘conservative, Midwestern and Methodist’, Hugh grew up to build a lifestyle empire like no other and also eventually earned the reputation of being a ‘ladies man’. Having been married thrice and involved in a string of love affairs, Hugh once claimed that he had slept with north of 1000 women during his lifetime spanning an impressive 91 years. So, let’s have a look at some of Hugh Hefner’s most famous romantic engagements that made headlines during the different phases of his life.

Mildred Williams

Hugh married his first wife Mildred Williams (whom he met during his stint at Northwestern University) back in 1949. However, when the media mogul got to know about the infidelity of his wife before the wedding, he was utterly devastated. Regardless, the marriage went on for a decade and finally, the couple divorced and went their separate ways in 1959. The couple has two beautiful children, David and Christie, together.

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Barbara Lynn Klein

After the divorce, Hugh met the famous supermodel Barbara Lynn Kelin in 1969 and got involved in a serious love affair that lasted until 1976. As was expected, Barbara continued to steal the limelight as Playboy’s cover girl in the years 1969, 1970, 1972 and 1985 and also changed her name to Barbi Benton as requested by Hugh. After her breakup with Hugh, Barbara went on to get married to the real estate hotshot George Gradow.

Shannon Tweed

After earning the title of the Playmate of the year, the popular star of ‘Falcon Crest’ fame Shannon Tweed allegedly got into a brief romantic engagement with Hugh Hefner in 1982. However, Shannon eventually moved on and married the famous vocalist Gene Simmons, raising two lovely kids together.


Carrie Leigh

One of the most highly publicized love affairs of its time, the Carrie Leigh-Hugh Hefner live-in relationship lasted for all of five years and ended on a grisly note when the former filed three lawsuits against the latter after their breakup. According to Carrie, Hugh had published some of her photos in the media without her permission. She further described the famous Playboy Mansion as a ‘cult’ and a place similar to the one described in the song Hotel California where ‘You can check out any time you like, but you can never leave'!


Kimberly Conrad

At the age of 26, Kimberly made it to the headlines by becoming the then 63-year-old Hugh Hefner’s second wife in 1989. The couple later separated following some ‘irreconcilable differences’ in 1998 and finally divorced in 2009. They had two children namely, Cooper and Marston.

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Brande Roderick

The sizzling actress from Baywatch and also the Playmate of the year in 2001, Brande Roderick hooked up with Hugh Hefner after his separation from Kimberly Conrad in 1998. However, the relationship did not last very long and Brande moved on to tie the knot with Glenn Cadrez (the famous NFL star) in 2001 and have a child with him. Intriguingly, the media mogul admitted in an interview with The Daily Beast that he had been dating multiple other women as well during his live-in relationship with Brande Roderick. While having an affair with Brande, Hugh met Sandy Bentley and Mandy Bentley and hooked up with them as well, and for the next two years, he had several live-in girlfriends.

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Tina Marie Jordan

Among the (allegedly) seven other women in his life during the first decade of the 2000s, a famous supermodel by the name Tine Marie Jordan too stole a considerable limelight and got the privilege of becoming the Playmate of the Month in 2002. Bridget Marquardt and Izabella St. James were also among the string of girlfriends that stayed at the Playboy Mansion as Hugh’s live-ins. Bridget Marquardt along with Kendra Wilkinson and Holly Madison featured on the six-season-long ‘the Girls Next Door’ that debuted back in 2005. Both Holly and Kendra too hooked up with Hugh Hefner at the same time. While Kendra later went on to marry Hank Baskett of Philadelphia Eagles, Holly tied the nuptials with Pasquale Rotella.

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Kristina and Karissa Shannon

The 20-year-old twins Kristina and Karissa Shannon, both got romantically involved with Hugh Hefner during 2008 and 2010 and stayed at the Playboy Mansion for two years. After their breakup, however, the twins moved out of the mansion and started living at the Playmate House in 2010. According to a few news reports, Hugh also dated Jenna Bentley during the same time in 2009.


Anna Sophia Berglund

It has been reported that Hugh Hefner also dated the 29-year-old model and actor Anna Sophia Berglund after his breakup with the Shannon twins and Jenna Bentley in 2011. Anna hailed from San Pedro, Los Angeles and featured in ‘Fired Up’.

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Crystal Harris

A 24-year-old model and actor, Crystal Harris began dating an 84-year-old Hugh Hefner and got engaged to him in December 2010. Although Crystal broke up the engagement with Hugh just before their wedding in 2011, the couple eventually got hitched in December of 2012. Crystal Harris is Hugh Hefner’s third wife. The couple did not have any kids together. Also, ever since Hugh died, Crystal Harris has avoided all paparazzi and also deleted her Instagram account. She has also set her Twitter account to private. According to some media reports, Crystal Harris will not receive any part of Hugh Hefner’s inheritance as stipulated in their prenuptial agreement.




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