Hugh Hefner Girlfriends 2022: Who Is Hugh Dating Now?

Hugh Hefner passed away on Wednesday, September 28, at the age of 91. Being the founder of Playboy Enterprises, he sure did live his life to the fullest with various women. Hefner was only legally married three times, but he does have a long list of girlfriends. Like really long. In honor of his passing, let’s take a trip down memory line.

Mildred Williams 1949 – 1959

Heard County Parks & Recreation

Hefner met Mildred when he was in college and the couple tied the knot in 1949. They had two children together, but it wasn’t happily ever after for them. Williams admitted to Hefner that she had an affair while he was away in the army. Hefner was heartbroken and Williams felt so guilty that she let Hefner sleep with other women to make up for her infidelity.

The two finally ended it and divorced in 1959.

Barbi Benton 1969 – 1976

Stanton Daily

Hefner met Barbi Benton when she landed a role on Playboy After Dark. People confirmed that the two lived together for nine years. Hefner even confessed that he regretted not putting a ring on it with Benton. This eventually led to their separation.

Carrie Leigh 1983 – 1988


For five years, Carrie Leigh was Hefner’s live-in girlfriend. When she finally packed her bags and left him, Leigh said that living in the mansion was “almost like a cult.” Interesting.

Kimberly Conrad 1989 – 2010

After having a few girlfriends, Hefner married Kimberly Conrad in 1989. They were together for nine years and had two children together. When that nine years was up, they decided to separate but stayed legally married for 11 years. The long separation came to an end after they sought a divorce.

Mandy & Sandy Bentley 1999 – 2000

These two girls were Hefner’s first twin live-in girlfriends, staying at the mansion for a year. They definitely were not the only twins in Hefner’s life. Of course.

Brande Roderick 2000 – 2001


Brande Roderick dated Hefner for one year. She was the Playmate of the Year in 2001. Before she became a playmate, she was an actress on Baywatch.

Holly Madison 2001 – 2008


Holly Madison was an original cast member on Girls Next Door. She moved into the mansion when she was only 21 years old. Madison and Hefner dated for seven years. After seven years, Madison decided to move out of the mansion. She moved out when she was 28.

Tina Marie Jordan 2000 – 2001


Tina Marie Jordan is an American glamour model and actress. Jordan was Playmate of the Month in March 2002. She dated Hefner for a year.

Izabella St. James 2002 – 2004


Izabella St. James was in law school when she met Hefner. She was invited to the mansion in 2002 and became his girlfriend. James wrote a tell-all book about what happens behind closed doors at the mansion. The book is called Bunny Tales: Behind Closed Doors at the Playboy Mansion.

Bridget Marquardt 2002 – 2009


Another member of the original cast of Girls Next Door, Bridget Marquardt also dated Hefner for several years.

Kendra Wilkinson 2004 – 2008


Kendra Wilkinson was also part of the original cast of Girls Next Door. While dating Wilkinson, He was also dating Marquardt and Madison at the same time.

Wilkinson also openly admitted to cheating on Hefner while they were still dating. You do you, Kendra! We all know he was pretty much doing the same.

Kristina & Karissa Shannon 2008 – 2010

Daily Mail/Getty Images

These are the second twins to move in with Hefner. The Shannons were also part of Girls Next Door, but when Hefner found out the twins had younger boyfriends coming over to the mansion, he kicked the girls out.

Crystal Harris 2012 – 2017

Daily Mail

Crystal Harris was 26 years old when she met Hefner in 2012. He was 86 years old at the time. The happy couple tied the knot on New Year’s Eve 2012. Harris and Hefner were together until his death.

We’re so sorry for your loss, Crystal.


Hugh Hefner was married to Crystal Harris in 2012 and he passed away on September 28, 2017 at the age of 91.

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