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Home > Celebrity > Hugh Hefner: How Many Women Did He Date In His Lifetime?

Hugh Hefner: How Many Women Did He Date In His Lifetime?

by Lokesh Bhardwaj
Tuesday, 22 February 2022, 01:17 IST
Secrets of Playboy Episode 5

source: Decider

Viewers who have watched the reality show “The Girls Next Door” back in 2005 were able to get a sneak peek at the Playboy Mansion and get an intimate look at the life of the founder Hugh Hefner his relationships. The Playboy magazine first came out in the year 1953. Since then, its founder has dated several girls, so let us just dig into his life of glamor and fame.

Hugh Hefner slept with about 1000 girls and more in his lifetime. The founder of the famous magazine has a luxurious and fancy mansion in Holmby Hills, just off Sunset Boulevard in LA, having an enormous footfall of celebrities and playmates. But not everyone is lucky enough to live in that mention; only his live-in girlfriends are allowed to stay.

Holly Madison, Bridget Marquardt, and Kendra Wilkinson are his girlfriends who share a closer bond with him. In the sensational American Tv show “The Girls Next Door,” women were seen as the eye candy. This show highlighted the beautiful girls and gave us a closer look inside the controversial mansion for six seasons, from 2005 to 2010.

Hugh Hefner – Lifetime 

Secrets of Playboy Episode 5
source: Decider

Hugh Marston Hefner, the founder (editor-in-chief) of the spice magazine and show – Playboy, passed away on September 27, 2017. His publication is famous for revealing photographs and articles about sex and pleasure.

He extended his brand into Playboy clubs that were nightclubs and resorts. The first club came into existence in 1960 in Chicago, and later on, many others were added to the list. In addition, he started his TV show in 2005, in which playmates shared wild parties and lifestyles with him.

Married Life of Hugh Hefner

The ladies’ man has been married three times and has dated several ladies since 1949. He claimed that he shared his bed with more than 1000 girls in his lifetime of 91 years, but only a few got the opportunity to be called his wives or girlfriends. His first wife was Mildred Williams back in 1949, and they crossed their paths in college, which was Northwestern University.

In one of his interviews, he talked about cheating on her before their marriage. They stayed together for a decade and parted ways in 1959. They have 2 kids together, Christie and David. After his first wife, another relationship that can be said to have some seriousness was with Barbara Lynn from 1969 and 1976. He even influenced her to change her name to Barbie Benton.

Another lady named Shannon Tweed also dated him in 1982, the playmate of the year. Carrie Leigh had a live-in relationship with the playboy for about 5 years in the ’80s. She later filed multiple lawsuits against him and called the mansion a ‘trap’ in one of her interviews.

Kimberley Conrad was the second wife of Hefner’s; she was just 26 years old when they got married in 1989. They also have 2 children, Marston and Cooper. Unfortunately, they got separated in 1998. They kept their divorce on a halt till 2009 because of their children, but his life was also filled with girls during that time. He dated multiple playmates, including actress Brande Roderick (Baywatch actress), one of the playmates in 2001.

Dating in the 2000s 

In the 2000’s he dated many girls, one of the most famous among them being Tina Marie Jordan, a playmate on the Playboy Show in 2022. After his breakup with Brande, he added more and more girls to his list. Finally, a girl named St. James moved into his mention in 2002 and stayed there for the next 2 years.

During 2005, he had 3 girlfriends simultaneously, namely, Kendra Wilkinson, Bridget Marquardt, and Holly Madison. This trio got mentioned on E! ‘s as well.

The Twins’ Story

The playboy dated 20- year- old identical twins named Karissa and Kristina Shannon, who were participants in the final season of “The Girls Next Door.” The twins moved out of the Playmate mansion in 2010 because of their relationship with younger boys.

Third and the Last Marriage

Secrets of Playboy Episode 5
source: MICE News Philippines

Hefner was two-timing Crystal Harris and the twins but married Crystal, who was 24 years old. Though there were ups and downs in their relationship because she broke off their engagement in 2011, they married in December 2012.

End of Playboy Legacy

The famous playboy passed away in 2017 because of sepsis from an E. coli Infection. After his death, his last wife vanished from social media, deleted her Instagram handle, and set her Twitter to a private setting. No one knows the reason, but as far as the guesses go, she will not inherit any of his fortunes because of her prenup. 

Tags: Hugh Hefner
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Lokesh Bhardwaj

Lokesh Bhardwaj

The only word in the dictionary which can describe Lokesh well is "Curious". He is a man who sits in the corner of a café, sipping his coffee and watch others and write about them having a good time. Addicted to bettering himself each day. An impressive introvert who finds his home in the places he travels. It's either the power of universe or sunsets that sets his soul free. In between, He can be found wrapped in his own bubble, knitting stories even before the sun rises!

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