American Playboy: The Many Wives and Girlfriends of Hugh Hefner

The 91-year-old founder of Playboy magazine was married three times and had a multitude of loves over the years.

Hugh Hefner was surrounded by his third wife, Crystal, and his three sons, Cooper, David, Marston, and daughter, Christie, when he passed away peacefully at the Playboy Mansion Wednesday.

The 91-year-old founder of Playboy magazine was married three times and had many loves over the years.

Read: World Mourns Hugh Hefner: The Playboy Legend Is Dead at 91

His Wives

Mildred Williams (1949-1959)

Hugh Hefner and Mildred Williams met in college at Northwestern University. The two married in 1949 and had two kids together: Christie, who was born in 1952, and David, born in 1955. While Hefner served in the U.S. Army, Williams had an affair that she admitted to him when he returned. He later said that hearing that his wife had strayed from their marriage was the most devastating moment of his life, according to reports. In an attempt to make up for the infidelity, she allowed him to sleep with other women. They divorced in 1959 after a decade of marriage.

(Hefner and 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 was 36 years her senior. The couple had two children together: Marston, born in 1990, and Cooper in 1991. After nine years of marriage, they legally separated and eventually divorced in 2010.

(Heffner and Harris in 2014 - Getty)

Crystal Harris (2012 – 2017)

Despite their 60-year age difference, Hefner and his third wife, Crystal, tied the knot in 2012. The couple had an on-again off-again engagement that began in 2010 with his proposing. They had a wedding planned for June 2011, but five days before the nuptials, she broke off the engagement. That same month, she was on the cover of Playboy to announce “Mrs. Crystal.” They married on New Year’s Eve 2012, when she was 26 and he was 86.

Watch: Why Hugh Hefner's Wife Crystal Had To Remove Her Breast Implants

His Girlfriends

(Hefner and Betton in 1970 - Getty)

Barbi Benton (1969-1976)

Benton became a subject on the short lived late-night series Playboy After Dark, where she and Hefner met. The duo lived together for nine years and he once told People magazine that he regrets never marrying her.

Carrie Leigh (1983-1988)

Leigh became Hefner’s first long-term girlfriend in the years after he and Benton split. Leigh lived with him in the Playboy Mansion for five years before she broke up with him and left.

(Hefner and 'The Girls Next Door' in 2007 - Getty)

The Girls Next Door Cast

Hefner was known for dating many women at once. At one point, he reportedly dated as many as seven women at a time, with the ladies living in the mansion with him. His most famous group of girlfriends came in the early 2000s when he invited cameras into his home to put his life on public display with the ladies on E!’s The Girl’s Next Door. Hefner dated Holly Madison, who was his No.1 girl, Kendra Wilkinson and Bridget Marquardt. After Hefner refused to have a baby with Madison, she ended their relationship and moved out of the mansion in 2008. He and Wilkinson split that same year, and Hefner and Marquardt broke up in 2009. 

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

Can't really put in to words how I really feel. It's easy to say he will be missed and how much I loved him. There's a lot more than that

September 28, 2017

Marquardt also expressed her condolences on Twitter Thursday.

So sad but forever grateful for all the wonderful memories and amazing experiences #RIPHef #Playboy ?

September 28, 2017

Kristina and Karissa Shannon (2008-2010)

After his split from the original Girls Next Door, Hefner invited twins Kristina and Karissa Shannon to move into his mansion and be a part of the show. His relationship with them lasted just two years. He reportedly broke up with them after finding out they had younger boyfriends come inside the home.

Watch: Ex-Playboy Model Accused of Affair With Donald Trump: I Have Class and Integrity