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Hugh Hefner's Many Lady Loves: All of the 'Playboy' Founder's Wives & Girlfriends through Years

Rebelander Basilan
May 23, 2021
11:00 A.M.

Hugh Hefner had three wives and a prodigious amount of girlfriends. Here are the women he married and had affairs with throughout his adult life.

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The late Hugh Hefner created "Playboy" magazine and enjoyed a playboy lifestyle. In total, he was married three times. However, he cohabited with a variety of women throughout his lifetime.

Even though he had been with hundreds of women, he only had a few who had the honor of being his girlfriend. Sometimes, Hefner, who died in 2017 at the age of 91, dated several women at once.

Hugh Hefner at his Los Angeles, California home, November 19, 2003. | Photo: Getty Images

Hugh Hefner at his Los Angeles, California home, November 19, 2003. | Photo: Getty Images

MILDRED WILLIAMS

Hefner exchanged his wedding vows with Williams in 1949. The former couple shared two children, daughter Christie and son David. After a decade, Hefner and Williams called it quits.

Hugh Hefner and his wife from 1949 t0 1959, Mildred Williams. | Photo: YouTube/BeforeTheyWereFamous

Hugh Hefner and his wife from 1949 t0 1959, Mildred Williams. | Photo: YouTube/BeforeTheyWereFamous

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BARBI BENTON

After splitting with Williams, Hefner began dating women from "Playboy." One of them was Barbara Lynn Klein, who took Barbi Benton's name at Hefner's request. Their relationship lasted from 1969 to 1976.

Hugh Hefner and Barbi Benton at Home of Warren Cowan in Beverly Hills, California, United States in 1973. | Photo: Getty Images

Hugh Hefner and Barbi Benton at Home of Warren Cowan in Beverly Hills, California, United States in 1973. | Photo: Getty Images

SHANNON TWEED

A Playmate of the Year in 1982, Tweed lived at the Playboy Mansion for over a year in the early 80s. At this time, she had a brief romance with Hefner, but they ended when she started dating Gene Simmons.

Shannon Tweed and Hugh Hefner on April 13, 1982 at Mann Chinese Theater in Hollywood, California. | Photo: Getty Images

Shannon Tweed and Hugh Hefner on April 13, 1982 at Mann Chinese Theater in Hollywood, California. | Photo: Getty Images

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CARRIE LEIGH

Hefner dated Leigh in the 1980s, and after moving out of the Playboy Mansion, she filed three lawsuits against him. According to her, he published unauthorized pictures of her during their time together.

Carrie Leigh and Hugh Hefner at Samuel Goldwyn Theater in Beverly Hills, California, United States in 1984. | Photo: Getty Images

Carrie Leigh and Hugh Hefner at Samuel Goldwyn Theater in Beverly Hills, California, United States in 1984. | Photo: Getty Images

KIMBERLEY CONRAD

The second wife of Hefner was Conrad. Hefner and Conrad were married in 1989, and they had two sons together, Marston and Cooper. Though they separated in 1998, Hefner didn't file for divorce until 2009.

Hugh Hefner and Kimberley Conrad on October 19, 1988 at the Beverly Hilton Hotel in Beverly Hills, California. | Photo: Getty Images

Hugh Hefner and Kimberley Conrad on October 19, 1988 at the Beverly Hilton Hotel in Beverly Hills, California. | Photo: Getty Images

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MANDY AND SANDY BENTLEY

After breaking up with Conrad, Hefner started dating various women. These women included twins, Mandy and Sandy. Hefner lived with them along with his other girlfriend at the same time.

Hugh Hefner and twins Mandy and Sandy Bentley at Playboy Lounge, celebrating the May issue as cover girls in 2000. | Photo: Getty Images

Hugh Hefner and twins Mandy and Sandy Bentley at Playboy Lounge, celebrating the May issue as cover girls in 2000. | Photo: Getty Images

BRANDE RODERICK

Roderick became Playmate of the Year in 2001 and also started a relationship with Hefner. Around this time, they had been together for less than a year. In the end, Roderick and Hefner broke up.

Brande Roderick and Hugh Hefner at Palms Hotel & Casino on May 2, 2009 in Las Vegas, Nevada. | Photo: Getty Images

Brande Roderick and Hugh Hefner at Palms Hotel & Casino on May 2, 2009 in Las Vegas, Nevada. | Photo: Getty Images

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IZABELLA ST. JAMES

After he and Roderick broke up, Hefner added more girls. He revealed a point where he had up to seven girlfriends, including St. James, who lived in the Playboy Mansion from 2002 until 2004.

Izabella St. James, Bridget Amarquardt, Hugh Hefner, Holly Madison at the The Palms Casino Resort in Las Vegas, Nevada in 2003. | Photo: Getty Images

Izabella St. James, Bridget Amarquardt, Hugh Hefner, Holly Madison at the The Palms Casino Resort in Las Vegas, Nevada in 2003. | Photo: Getty Images

HOLLY MADISON

The most well-known of Hefner's girlfriends might have been Madison, whom he dated from 2002 until she left the mansion in 2008. She had wanted to marry Hefner and have children with him, but he refused.

Hugh Hefner and Holly Madison at The Loews Beverly Hills Hotel in Beverly Hills, California, United States in 2005. | Photo: Getty Images

Hugh Hefner and Holly Madison at The Loews Beverly Hills Hotel in Beverly Hills, California, United States in 2005. | Photo: Getty Images

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BRIDGET MARQUARDT

During Marquard's stay in the Playboy Mansion in 2002, her relationship with Hefner was featured in "Girls' Next Door." Marquard remained there until 2009 and ultimately ended up with director Nicholas Carpenter.

Holly Madison, Hugh Hefner, and Bridget Marquardt at The Playboy Club at The Palms Hotel and Casino Resort in Las Vegas, Nevada in 2007. | Photo: Getty Images

Holly Madison, Hugh Hefner, and Bridget Marquardt at The Playboy Club at The Palms Hotel and Casino Resort in Las Vegas, Nevada in 2007. | Photo: Getty Images

KENDRA WILKINSON

Wilkinson's first encounter with Hefner took place at a birthday party in 2004. Shortly after that, he asked her to move in with him and be his girlfriend. In 2009, Wilkinson opted to move out of the mansion.

Kendra Wilkinson and Hugh Hefner at Nine Steakhouse at the Palms Resort & Casino on April 4, 2009 in Las Vegas, Nevada. | Photo: Getty Images

Kendra Wilkinson and Hugh Hefner at Nine Steakhouse at the Palms Resort & Casino on April 4, 2009 in Las Vegas, Nevada. | Photo: Getty Images

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KRISTINA AND KARISSA SHANNON

Kristina and Karissa moved into the mansion in 2008 but left it by 2010. In retrospect, Kristina and Karissa explained that their relationship with Hefner was more fun than romantic.

Karissa Shannon, Kristina Shannon, Hugh Hefner, and Crystal Harris at Sony Pictures Studios on June 11, 2009 in Culver City, California. | Photo: Getty Images

Karissa Shannon, Kristina Shannon, Hugh Hefner, and Crystal Harris at Sony Pictures Studios on June 11, 2009 in Culver City, California. | Photo: Getty Images

CRYSTAL HARRIS

Hefner and Harris started dating in 2009 despite Harris being 60 years younger than him. Their engagement took place in 2010. However, six months later, she ended their relationship.

They had just scheduled their nuptials days before they broke up. A reconciliation occurred between Hefner and Harris, and the couple got married in 2012. She was his wife until he died in 2017.

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Crystal Harris and Hugh Hefner on May 9, 2013 in Holmby Hills, California | Photo: Getty Images

Crystal Harris and Hugh Hefner on May 9, 2013 in Holmby Hills, California | Photo: Getty Images

Harris insisted that her unconventional relationship with Hefner is made out of love, despite the opinions of others. During an interview, she emphasized how much he loved her and how much she loved him.

Hefner, who estimated that he had slept with more than 1,000 women, once spoke about Harris in an interview. According to the multi-millionaire, he was a happy person with only one woman in his life.

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