The 91-year-old founder that Playboy magazine to be married 3 times and also had a multitude that loves end the years.

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Hugh Hefner was surrounded by his 3rd wife, Crystal, and also his three sons, Cooper, David, Marston, and daughter, Christie, as soon as he passed away peacefully at the Playboy Mansion Wednesday.

The 91-year-old founder that Playboy magazine was married 3 times and had countless loves end the years.


Mildred Williams (1949-1959)

Hugh Hefner and also Mildred Williams met in college at Northwestern University. The 2 married in 1949 and also had two kids together: Christie, who was born in 1952, and also David, born in 1955. While Hefner offered in the U.S. Army, Williams had actually an affair the she admitted to him as soon as he returned. He later on said that hearing the his wife had strayed native their marital relationship was the most damaging moment the his life, according to reports. In an effort to comprise for the infidelity, she enabled him to sleep with other women. They divorced in 1959 ~ a te of marriage.


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(Hefner and also Conrad in 1998 -Getty)

Kimberley Conrad (1989-2010)

Conrad, who was Playboy"s "Playmate of the Month" in January 1988, married Hefner in 1989. He to be 36 years she senior. The couple had two children together: Marston, born in 1990, and also Cooper in 1991. After ripe years that marriage, castle legally separated and eventually divorce in 2010.

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(Heffner and also Harris in 2014 - Getty)


Crystal Harris (2012 – 2017)

Despite their 60-year period difference, Hefner and his 3rd wife, Crystal, bound the node in 2012. The couple had an on-again off-again engagement that began in 2010 through his proposing. They had actually a wedding planned for June 2011, however five days before the nuptials, she broke off the engagement. That very same month, she was on the cover of Playboy come announce “Mrs. Crystal.” lock married on new Year’s night 2012, as soon as she was 26 and also he was 86.

Watch: Why Hugh Hefner"s wife Crystal had To remove Her breast Implants

His Girlfriends

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(Hefner and Betton in 1970 - Getty)


Barbi Benton (1969-1976)

Benton came to be a topic on the brief lived late-night collection Playboy after ~ Dark, wherein she and also Hefner met. The duo lived together for ripe years and he when toldPeople magazine the he regrets never ever marrying her.

Carrie Leigh (1983-1988)

Leigh became Hefner’s very first long-term girlfriend in the year after he and also Benton split. Leigh lived with him in the Playboy Mansion for 5 years prior to she damaged up v him and also left.

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(Hefner and also "The Girls following Door" in 2007 - Getty)


The Girls next Door Cast

Hefner was known for dating many women at once. In ~ one point, he reportedly dated as plenty of as 7 women at a time, with the females living in the mansion with him. His most renowned group that girlfriends come in the at an early stage 2000s once he invited cameras right into his house to put his life on windy displaywith the ladies on E!’s The Girl’s following Door. Hefner date Holly Madison, who was his No.1 girl, Kendra Wilkinson and also Bridget Marquardt. After Hefner refused to have actually a baby through Madison, she ended their relationship and moved out of the mansion in 2008. He and Wilkinson break-up that same year, and Hefner and Marquardt broke up in 2009.

Following Hefner’s passing, Wilkinson tweeted “Can’t really put in come words just how I yes, really feel.”

Can"t really put in to words how I really feel. It"s basic to to speak he will certainly be missed and how lot I love him. There"s a lot an ext than that

September 28, 2017

Marquardt likewise expressed her condolences ~ above Twitter Thursday.

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So sad yet forever grateful for every the wonderful memories and also amazing experiences #RIPHef #Playboy ? pic.twitter.com/RkHje7h0Un

September 28, 2017

Kristina and Karissa Shannon (2008-2010)

After his separation from the initial Girls next Door, Hefner invite twins Kristina and Karissa Shannon to move right into his mansion and also be a component of the show. His partnership with lock lasted simply two years. That reportedly damaged up v them after ~ finding out they had younger boyfriends come within the home.