Hugh Hefner’s Partners: All of the ‘Playboy’ Creator’s Wives & Girlfriends Through the Years

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January 24, 2022 3:15PM EST
Hughe and Crystal Hefner
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Hugh Hefner was best known for creating ‘Playboy’ magazine, but he was also known for his playboy lifestyle. When Hugh died at the age of 91 in 2017, he had been married three times, but there were plenty of other women in his life throughout his years. While the magazine creator had been with hundreds of women, there were a handful that also got to be his official ‘girlfriends.’ Hugh sometimes dated many women at one time, as well.

During ‘The Girls Next Door’ years, Hugh dated Holly Madison, Bridget Marquardt, and Kendra Wilkinson all at the same time, and all three lived in the Playboy mansion with him. Hugh was married to Crystal Hefner at the time of his death, and her new memoir, ‘Only Say Good Things: Surviving Playboy and Finding Myself’ hit shelves in January of 2024.

Click through to see photos of Hugh’s wives and girlfriends over the years in our official gallery.

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Hugh & ‘The Girls Next Door’

Hugh & ‘The Girls Next Door’
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Hugh’s lifestyle was depicted on the E! reality series’ Girls Next Door,’ which aired from 2005 until 2010. The show mostly followed Hugh’s relationships with models Holly Madison, Bridget Marquardt, and Kendra Wilkinson. 

Here, the blonde beauties pose with the late Playboy magnate in sexy two piece costumes.

May 17, 2021, 12:10PM
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Hugh Hefner & Sondra Theodore

Hugh Hefner & Sondra Theodore
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Sondra Theodore is one of Hugh Hefner’s former girlfriends. She dated Hefner from 1976 to 1981.

January 24, 2022, 2:17PM
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Mildred ‘Millie’ Williams

Mildred ‘Millie’ Williams
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Before he became the ‘Hef’ who the world knows today, Hugh was married to Mildred Williams from 1949 until 1959.

The two had a daughter, Christie, who was born in 1952, and a son, David, who was born in 1955, together. Mildred came clean about having an affair while Hef was away in the army, before the two were even married. Hef later claimed that Mildred would let him sleep with other women to make up for this infidelity. Still, the marriage came to an end after ten years.

May 17, 2021, 12:33PM
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Hugh Hefner & Barbi Benton

Hugh Hefner & Barbi Benton
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After ending things with Mildred, Hef began to date various playmates from ‘Playboy’ magazine.

One of those women was Barbara Lynn Klein, who changed her name to Barbi Benton at Hugh’s request. The two were together from 1969 until 1976. Barbi was a ‘Playboy’ covergirl in 1968, 1970 and 1972, followed by another appearance in 1985, as well.

May 17, 2021, 12:13PM
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Shannon Tweed

Shannon Tweed
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Shannon lived at the Playboy Mansion for more than a year in the early 80s, and she wound up being named Playmate of the Year in 1982. She and Hef briefly dated around this time, but split when she started dating her now-husband, Gene Simmons.

May 17, 2021, 12:14PM
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Hugh Hefner & Carrie Leigh

Hugh Hefner & Carrie Leigh
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In the 1980s, Hugh also dated Carrie Leigh, who lived with him at the Playboy Mansion for five years.

After moving out, Carrie filed three lawsuits against Hef. One claimed that he published unauthorized photos of her during their time together. Later, she described living in the mansion as “almost like a cult”, adding, “When you live in an environment like that, that’s so different from how other people live, you start forgetting who you are and what you believe is right.”

May 17, 2021, 12:16PM
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Hugh Hefner & Kimberley Conrad

Hugh Hefner & Kimberley Conrad
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Hugh’s second wife was Kimberely Conrad. She was just 26 years old when they tied the knot — more than 35 years younger than Hef. Hugh and Kimberely were married in 1989, which was the same year she was named Playmate of the Year. They had two sons — Marston, born 1990, and Cooper, born 1991 — together.

Hef and Kimberely separated in 1998, but remained legally married for the sake of their sons. It wasn’t until 2009 — when the pair’s youngest child was 18 — that Hef finally filed for divorce.

May 17, 2021, 12:16PM
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Hugh Hefner With Mandy & Sandy Bentley

Hugh Hefner With Mandy & Sandy Bentley
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Following his split from Kimberley, Hugh once again began dating various women. Two of those women included twins, Mandy and Sandy Bentley. The twins lived with Hef, along with his other girlfriend, Brande Roderick, at the same time.

May 17, 2021, 12:17PM
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Hugh Hefner & Brande Roderick

Hugh Hefner & Brande Roderick
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Brande was Playmate of the Year in 2001, and also began a relationship with Hef. They were together for less than a year around this time. Eventually, Brande and Hef ended things, and she wound up marrying Glenn Cadrez in 2007 (they later split).

May 17, 2021, 12:18PM
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Izabella St. James

Izabella St. James
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Another one of Hef’s ladies in the early 2000s was Izabella St. James.

“When the relationship with Brande broke up, I added more girls,” he explained, adding that, at one point, the number of girlfriends he had was up to seven. That included Izabella, who lived in the Playboy Mansion from 2002 until 2004.

May 17, 2021, 12:19PM
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Hugh Hefner & Holly Madison

Hugh Hefner & Holly Madison
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Perhaps Hugh’s most well-known girlfriend was Holly Madison. Holly was Hef’s “number one girl” during the era of ‘Girls’ Next Door.’ They were together from 2002 until Holly left the mansion in 2008. Although Holly wanted to marry Hef and have kids with him, he was adamant that marriage was not part of his plan anymore. 

Since leaving the Playboy Mansion, Holly has been very open about her time with Hef. She was admittedly in a “desperate” financial situation when she opted to move in with him. Holly described the situation in the mansion as “cutthroat” between the different women, and admitted that she began having thoughts of ending her own life before deciding to leave for good.

May 17, 2021, 12:21PM
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Hugh Hefner & Bridget Marquardt

Hugh Hefner & Bridget Marquardt
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Like Holly, Bridget Marquardt’s relationship with Hef was featured on ‘Girls’ Next Door.’ She moved into the Playboy Mansion in 2002, despite still being married to another man (they were in the process of divorcing at the time). Bridget stayed in the Playboy Mansion until 2009, and eventually got engaged to director Nicholas Carpenter.

May 17, 2021, 12:23PM
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Hugh Hefner & Kendra Wilkinson

Hugh Hefner & Kendra Wilkinson
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Kendra Wilkinson met Hef while working at one of his birthday parties in 2004. He asked her to move in with him and be his girlfriend shortly afterward. In 2009, Kendra met her eventual husband, Hank Baskett, and opted to move out of the mansion. She and Hank have two kids together, but are divorced. 

May 17, 2021, 12:24PM
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Hugh Hefner With Kristina & Karissa Shannon

Hugh Hefner With Kristina & Karissa Shannon
Joshua Gates Weisberg/EPA/Shutte

With Holly, Kendra and Bridget out of the mansion, the final season of ‘Girls’ Next Door’ featured a new group of women, including twins Kristina and Karissa Shannon. The girls moved into the mansion in 2008, but already moved out by 2010. They have since said that their relationship with Hef was more about “fun” than romance.

May 17, 2021, 12:27PM
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Hugh Hefner & Crystal Harris

Hugh Hefner & Crystal Harris
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Crystal Harris was the other, new main cast member on the final season of ‘Girls’ Next Door.’ Despite Crystal being 60 years younger than Hef, the two started dating in Jan. 2009. Hugh and Crystal got engaged on Christmas Eve 2010, but she broke it off just six months later. The breakup was just days before the pair’s planned nuptials. 

Eventually, Crystal and Hef reconciled and were married on New Year’s Eve 2012. Crystal was Hef’s wife until his eventual death in Sept. 2017

May 17, 2021, 12:29PM