Hugh Hefner: A History of Romance

Hugh Hefner - The Hollywood Sign Trust - 2010
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The Playboy creator, who was recently jilted by young bride Crystal Harris, has had a laundry list of great loves over his lifetime.

The split between Hugh Hefner and his runaway bride, Crystal Harris, turned ugly this week when Harris guested on Howard Stern’s radio show to share details about the intimacies of their relationship. The Playboy founder fired back on Twitter, saying: “I feel sorry for Crystal. She seems lost.” He later added, “Crystal convinced me that she adored me. That was the first lie.”

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In his 85 years, Hefner has had many great loves. We take a look back on some of the most notable ladies to walk on his arm.

Long before Playboy, Hefner married Northwestern University student Mildred Williams in 1949. In their ten years of marriage, ending in a 1959 divorce, the couple had two children together. Hef’s first real heartbreak came prior to tying the knot, when Williams admitted to engaging in an affair during his time in the Army. In an attempt to lessen her guilt and save their relationship, Williams allowed the future mogul to become involved with other women during their marriage.

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Among a bevy of flings with Playmates and models, Barbi Benton earned a spot as a standout girlfriend in 1969. She famously dated Hefner until 1976. The couple split amicably with Benton and Hefner remaining close friends, as documented on the E! reality series, The Girls Next Door.

Before becoming Gene Simmons’ longtime love, Shannon Tweed briefly dated Hefner in the early ‘80s during her time as a Playmate.

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Hefner married again, just once, to Playmate of the Year, Kimberley Conrad in 1989. The couple had two children before separating in 1998, at which point Conrad and the two boys moved out of the Playboy mansion and into a house next door. It wasn’t until 20 years later that Hefner and Conrad officially divorced.

The media spotlight shone bright on Hefner’s unconventional lifestyle in 2005, when The Girls Next Door debuted on E!. The show featured Hef and his three live-in girlfriends, Holly Madison, Bridget Marquardt and Kendra Wilkinson, as they engaged in a fascinating and unusual relationship.

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The show skyrocketed the girls to fame, with Madison and Wilkinson each earning their own spinoffs, while Marquardt landed a show on the Travel Channel. After one season of Bridget’s Sexiest Beaches, the former Girl Next Door filmed a pilot for E!, which was not picked up.

After famously refusing to marry Madison, despite her not-so-subtle hints, Hef moved on with 20-year old twins Kristina and Karissa Shannon, before popping the question to his “Number One” girlfriend at the time, Harris.

Not one to let a lady keep him down, Hef rebounded quickly with two new girlfriends. He is currently “in a better place” with 25-year old Anna Sophia Berglund and 24-year old Shera Bechard. According to his Twitter feed, the trio enjoys watching Dexter and playing dominos.