Hugh Hefner’s Ex-Girlfriends And Wives Through The Years

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If you have heard of the popular Playboy Magazine, you would know that its founder Hugh Hefner who died on September 27, 2017, did not just build himself an empire but also a reputation of being the ladies man. Hefner’s escapades date as far back as 1949 and in an interview conducted before his demise, he revealed that he had slept with more than 1,000 women, however, he had been married only 3 times throughout his adventurous 91 years of life.

Hugh Hefner’s Women: Wives And Ex-girlfriends

Let’s take a look at Hefner’s women starting from the first to the last one in his life before he died.

1. Mildred Williams

Mildred was Hefner’s first wife with whom he had his daughter Christie and son David. The couple met while at the Northwestern University, fell for each other and eventually got married in 1949. However, to Hefner’s dismay, Mildred confessed she was unfaithful before their wedding while he was in the army.

They stayed married for another 10 years before calling it quits in 1959.

2. Barbara Lynn Klein

Hefner and Barbara were an item from 1969 to 1976 and he is said to have convinced her to change her name to Barbi Benton. Benton was not only his girlfriend but the face of Playboy magazine in 1969, 1970, 1972 and even in 1985 after their split. Benton is said to be one of Hefner’s greatest love and he regretted why they did not get married.

3. Shannon Tweed

Shanon was named Playmate of the year in 1982 which in a way ended up making her Hefner’s girlfriend, however, their relationship was shortlived.

4. Carie Leigh

Leigh is said to have dated Hefner for 5 years in the 80’s before breaking up with 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 an interview with The Washington Post in 1999 that the Playboy Mansion was like a cult in which the girls living there were all prisoners.


5. Kimberley Conrad

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

They separated in 1998 but it was in 2009 that Hefner filed for divorce on the grounds of irreconcilable differences and he revealed to People’s magazine that he waited that long because Kimberley wanted to stay in the marriage for the sake of their kids.

6. Brande Roderick

After Hefner’s separation from his second wife in 1998, sources have it that he dated lots of women including actress Brande Roderick who was Playmate of the year in 2001 and is known to have been featured in the film Baywatch.

7. Sandy And Mandy Bentley

Twins Sandy and Mandy along with Brande Roderick were said to be Hefner’s live-in girlfriends at the Playboy mansion for about 2 years. It actually sounds crazy to have 3 live-in girlfriends but yeah, the ladies man pulled it off.

8. Tina Marie Jordan

In the early 2000’s Hufner is said to have dated Tina Jordan who was the playmate for the month of March in 2002.

9. Izabella St. James

After the Playboy founder broke up with Brande and the twins, he increased the number of his girlfriends to 7 which include 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 is the trio live-in girlfriends Holly Madison, Bridget Marquardt and Kendra Wilkinson who were featured in the show The Girls Next Door aired on E! which made its debut in 2005 and ran for six seasons.

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

11. Twins Karissa And Kristina

Hefner seems to have a thing for twins as he dated another set of 20-year-old twins named Karissa and Kristina and he even featured them in the final season of the show The Girls Next Door. The twins who later started dating younger men were asked to leave the Playboy mansion and move to the Playmate House in 2010.

12. Crystal Harris

Hugh Hefner’s third and last wife was one of his girlfriends Crystal Harris whom he got engaged to in 2010 when she was 24 and he was 84. Although she was said to have called off the engagement for reasons unknown to the public they still managed to get back together and proceded with the wedding in 2011.

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

Also Read: Top 10 Richest People in the world with full biography and details.