Hugh Hefner’s Ex-Girlfriends And Wives Through The Years
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If you’ve heard of the popular Playboy magazine, you know that its founder, Hugh Hefner, who died on September 27, 2017, not only built an empire, but also a reputation for being the ladies’ man. Hefner’s escapades date back to 1949, and in an interview, he conducted before his death, he revealed that he had slept with more than 1,000 women, but had only been married three times in his adventurous 91 years.

Hugh Hefner’s Women: Wives And Ex-girlfriends

Let’s take a look at Hefner’s wives, from the first to the last in his life before his death.

1. Mildred Williams

Mildred was Hefner’s first wife, with whom he had his daughter Christie and his son David. The couple met at Northwestern University, fell in love, and eventually married in 1949, but to Hefner’s dismay, Mildred confessed that she had been unfaithful to him before her marriage while he was in the army.

They remained married for another 10 years before they stopped in 1959.

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2. Barbara Lynn Klein

Hefner and Barbara were a topic of conversation from 1969 to 1976, and he is said to have convinced them to change their name to Barbi Benton. Benton was not only his girlfriend but also the face of Playboy magazine in 1969, 1970, 1972, and even 1985 after their separation. Benton is said to have been one of Hefner’s greatest loves, and he regretted why they didn’t get married.

3. Shannon Tweed

Shanon was elected Playmate of the Year in 1982, which in a way led to her becoming Hefner’s girlfriend, but their relationship was short-lived.

4. Carie Leigh

Leigh is said to have dated Hefner for 5 years in the ’80s before she separated from him, moved out of the Playboy mansion, and even filed 3 lawsuits against him, which included publishing her photos without her consent.

Leigh had revealed in a 1999 interview with the Washington Post that the Playboy Mansion was like a cult where the girls living there were all prisoners.

5. Kimberley Conrad

In 1989, Hefner took a second wife named Kimberley, who was 26 years old while he was 63. The couple married at the Playboy Mansion and had two children, Marston and Cooper.

They separated in 1998, but it wasn’t until 2009 that Hefner filed for divorce due to irreconcilable differences, and he revealed to People’s magazine that he had waited so long because Kimberley wanted to stay in the marriage for the sake of her children.

6. Brande Roderick

After Hefner’s separation from his second wife in 1998, sources say he met with many women, including actress Brande Roderick, who was named Playmate of the Year in 2001 and was featured in the film Baywatch.

7. Sandy And Mandy Bentley

The twins Sandy and Mandy as well as Brande Roderick are supposed to be Hefner’s friends who have been living in the Playboy Mansion for about 2 years. It does sound crazy to have 3 girlfriends, but yes, the man-woman has done it.

8. Tina Marie Jordan

In early 2000, Hufner is said to have gone out with Tina Jordan, who was the playmate of the month is March 2002.

9. Izabella St. James

After the Playboy founder split up with Brande and the twins, he increased the number of his girlfriends to 7, including Izabella St. James, who lived in the Playboy mansion for two years.

10. Holly Madison, Bridget Marquardt, and Kendra Wilkinson

Next on Hugh Hefner’s list are three friends, Holly Madison, Bridget Marquardt, and Kendra Wilkinson, who appeared on E! in The Girls Next Door, which debuted in 2005 and ran for six seasons.

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When the girls left the mansion, Wilkinson married Hank Baskett, who played for the Philadelphia Eagles, and they now have two children, a daughter, and a son. Madison also married and has two children with her husband Pasquale Rotella.

11. Twins Karissa And Kristina

Hefner seems to have a fondness for twins, as he was with another group of 20-year-old twins named Karissa and Kristina, whom he even showed on the last season of The Girls Next Door. The twins, who later got together with younger men, were asked to leave the Playboy Mansion and move to Playmate House in 2010.

12. Crystal Harris

Hugh Hefner’s third and last wife was one of his girlfriends Crystal Harris, with whom he got engaged in 2010 when she was 24 and he was 84 years old. Although she allegedly broke off the engagement for reasons unknown to the public, they managed to get back together and continue with the wedding in 2011.

After his death, it was reported that Hefner did not mention Crystal in his will, which excludes her from claiming any part of his assets.