Hugh Hefner’s Romances: His Wives and Girlfriends Through the Years

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Hugh Hefner’s Romances: His Wives and Girlfriends Through the Years

Hugh Hefner, who died in September 2018 at age 91, was always surrounded by beautiful women. The Playboy founder married three times, but was mostly recognized for having multiple live-in girlfriends at the Playboy Mansion.

Though the media mogul tried his hand at marriage, his first two attempts— to childhood sweetheart Mildred Williams from 1949 to 1959, and to Kimberley Conrad from 1989 to 2010 — didn't last. He is survived by his third wife, Crystal Hefner (née Harris), as well as four adult children from his two previous marriages. (Hugh shared Christie and David with Williams and Marston and Cooper with Conrad.)

Hugh’s love life was the subject of the Girls Next Door reality TV series, which aired on E! from 2006 to 2009. The six-season series primarily highlighted his relationships with the likes of Holly Madison, Bridget Marquardt and Kendra Wilkinson. The final season of the show introduced Crystal, and twins Kristina and Karissa Shannon.

“I've been blessed for many, many things but to find true love at this age, at this stage of life, is beyond words," Hugh previously told E! News in 2014, two years after marrying Crystal. "Things could not be better.”

After the former magazine editor’s death, Crystal exclusively opened up about her loss to Us Weekly.

“It’s been a whirlwind,” Crystal told Us in March 2020. “It’s been trying to find myself. I became someone else’s identity for 10 years. I’m finding my own identity and place in the world. It’s scary. … I’ve been doing a lot of traveling and seeing the world. I didn’t do much of that living at the house. Hef and I were just homebodies. He didn’t like me traveling. I guess I’m making up for lost time.”

Hugh’s past relationships made headlines once again after the January 2022 premiere of the A&E docuseries Secrets of Playboy. The Vegas Diaries author and other former Playmates came forward with allegations about the Illinois native’s inappropriate behavior during his mansion residency.

“We sign our names to support Hugh M. Hefner. From all we know of Hef, he was a person of upstanding character, exceptional kindness and dedication to free thought,” a collective of former Playboy employees and models wrote in a joint statement, obtained by Us Weekly, in February 2022. “He demonstrated a commitment to living an honest life beyond everything else. Our time within Hugh Hefner’s Playboy and the organization’s subsidiaries remains a period all of us are fond of.”

Scroll through to look back at the icon’s greatest loves:

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Mildred Williams

Before he launched the magazine in 1953, Hefner had already fallen in love with Mildred “Millie” Williams. The pair were together during his stint in the army from 1944 to 1946, and when he returned he found out Williams had an affair with another man. The couple married anyway in 1949, and in his E! True Hollywood Story from 2006 it was revealed that she allowed him to have relationships with other women during their marriage to lessen her guilt. They had two children together but ended their 10-year marriage in 1959.  

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Marilyn Cole

British model Cole had a brief relationship with the businessman. She was 1973’s Playmate of the Year and eventually married Victor Lownes, who was once president of the Playboy Enterprises.

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Lillian Muller

Muller first met Hefner in the 1970s after a scout for his empire found her in London. She became Playmate of the Year in 1976 and appeared on the magazine’s cover eight times. The pair were an item from 1976 to 1977 and stayed friends after their romance ended.

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Barbi Benton

After his first marriage ended, Hefner began dating and having flings with several Playboy models. He dated Playmate Benton starting in 1969. The couple lived together and split in 1976. The two remained friends and she even appeared in an episode of the E! reality show The Girls Next Door in 2005, which featured the mogul's then-girlfriends Madison, Wilkinson and Marquardt. Hefner has admitted that not marrying Benton was one of his biggest regrets.

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Carrie Leigh

Leigh lived with Hefner for five years in the 1980s. After leaving the Playboy Mansion, she filed lawsuits against the magazine publisher — one palimony suit and one for publishing unauthorized photos of her.

"It's almost like a cult," she told The Washington Post in 1999. "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.”

She added: “It took me a few years after I did leave to wipe it out of my head."

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Kimberley Conrad

The Playboy mogul married his second wife in 1989, and they had sons Marston and Cooper during their marriage. The couple separated in 1998 but didn’t officially divorce until 11 years later in 2010.

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Mandy and Sandy Bentley

Hefner dated twin sisters Mandy and Sandy Bentley from 1999 to 2000 and they lived with him for a year. The Bentley twins appeared on the May 2000 cover of Playboy.

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Brande Roderick

Roderick was a Playmate in the late '90s and dated Hef for a year from 2000 to 2001 before marrying former football player Glenn Cadrez in 2007. 

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Izabella St. James

St. James dated Hefner from 2002 to 2004 after meeting him when she was 26. St. James used her experience at the Playboy Mansion to write her tell-all memoir titled Bunny Tales: Behind Closed Doors at the Playboy Mansion.

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Holly Madison

Madison was in a relationship with Hefner for seven years, starting in 2001. She lived in the mansion until she was 28 years old, and was one of the three girlfriends who starred on The Girls Next Door. They split after Hefner refused to get married, and she went on to write a tell-all book titled Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny.

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Kendra Wilkinson

Wilkinson also starred in the reality series The Girls Next Door alongside Hefner and his two other girlfriends, which ran for six seasons on E! from 2005 to 2010. The pair maintained a friendship over the years, and she was distraught to hear about his passing.

"Hef changed my life," the Playboy model told Us Weekly in a statement. "He made me the person I am today. I couldn't be more thankful for our friendship and our time together. I will miss him so much but he will be in my heart forever."

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Bridget Marquardt

Marquardt dated Hefner for seven years, and they went their separate ways in 2009. She was one of the three girlfriends to be in the cast for The Girls Next Door.

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Kristina and Karissa Shannon

Kristina and Karissa dated Hefner in 2008 and became his live-in girlfriends, alongside his No. 1 girlfriend, Crystal. It was reported by Fox News that the twins were eventually kicked out of the mansion for breaking the “no boys” rule, and dating younger men while living in the house. 

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Crystal Harris

Hugh proposed to Crystal in 2010. But in June 2011, just five days before their wedding, she ended the engagement. They eventually reconciled and married on New Year’s Eve in 2012, when he was 86 years old and she was 26.