A look at Hugh Hefner's wives, girlfriends through the years


Hugh Hefner has made headlines posthumously as A&E recently released its docuseries about the Playboy founder, “Secrets of Playboy.” 

Although Hefner died in 2017, many former Playboy Playmates have come forward to detail their alleged experiences with Hefner and the Playboy mansion in the new docuseries, including Holly Madison and Sondra Theodore.

In addition to Madison and Theodore, here’s a look at Hefner’s wives and girlfriends through the years.

Mildred Williams

Williams was the first wife of Hugh Hefner. The two met in college and got married in 1949. During their marriage, Hefner and Williams raised two children, Christie and David.

The two divorced in 1959.

Barbi Benton

Hugh Hefner met Barbi Benton in 1968, and the two dated until 1979.

Hugh Hefner met Barbi Benton in 1968, and the two dated until 1979.

Benton met Hefner in 1968 when she was 18, and he was 42. The pair dated until 1976. 

She went on to marry Los Angeles entrepreneur George Gradow in 1979. Benton appeared on “Playboy After Dark,” and after she split with Hefner went on to do modeling, singing and acting.


Sondra Theodore

Sondra Theodore and Hugh Hefner

Sondra Theodore and Hugh Hefner
(Ron Galella/Ron Galella Collection via Getty Images)

Theodore met Hefner when she was 19 and he was 50 in the late ’70s. Theodore was one of Hefner’s exes who spoke out in the docuseries.

She recently spoke to Fox News Digital, where she alleged that Hefner manipulated her into participating in an orgy.

Carrie Leigh

Leigh dated Hefner and lived in the Playboy mansion for five years in the 1980s. She has been candid about her experience since leaving the mansion, describing it as an alleged “cult” during an interview with the Washington Post in 1999.

Leigh is an actress, most known for her roles in “A Fine Mess” and “The New Mike Hammer.”

Kimberley Conrad

Conrad was Hefner’s second wife. The two married in 1989 and remained married until 2009, despite separating in 1998. Conrad and Hefner had two sons together, Marston and Cooper. Cooper has recently spoken out, defending his late father amid the shocking A&E documentary. 

Mandy and Sandy Bentley

Mandy and Sandy were the first set of twins that Hefner dated simultaneously around 2000. They lived in the Playboy mansion with Hefner and his other girlfriend at the time, Brande Roderick

Brande Roderick

Roderick dated Hefner for roughly a year from 2000-2001. 

Roderick was named Playmate of the Year in 2001. Roderick is a model and actress most known for her appearances in “Baywatch,” “The Apprentice” and “Starsky & Hutch.”

Holly Madison

Holly Madison dated Hugh Hefner from 2001 until 2008.

Holly Madison dated Hugh Hefner from 2001 until 2008.
(Chad Buchanan/Getty Images)

Madison moved into the Playboy mansion at the age of 21. She dated Hefner from 2001 until 2008. Madison starred in “Girls Next Door” alongside Bridget Marquardt and Kendra Wilkinson.

She went on to have her own show, “Holly’s World.”

In the A&E doc, Madison claimed she was afraid to leave the Playboy Mansion out of fear of repercussions, specifically a “mountain of revenge porn” that the late publisher allegedly had in his possession.


Tina Marie Jordan

Hefner dated Tina Marie Jordan for one year in 2000-2001. Following her time in the “Playboy” videos, Jordan made appearances on “Howard Stern,” “Late Night Poker” and “The Girls Next Door.”

She also hosted the radio show “Two Chicks and a Bunny” from 2004 until 2006.

Izabella St. James

St. James dated Hefner from 2002 until 2004. She was in law school when she met Hefner. Since her time living in the mansion, St. James wrote the book “Bunny Tales: Behind Closed Doors at the Playboy Mansion” detailing her experience.

Bridget Marquardt

Bridget Marquardt dated Hugh Hefner from 2002 until 2008.

Bridget Marquardt dated Hugh Hefner from 2002 until 2008.
(Neilson Barnard/Getty Images)

Marquardt dated Hefner from 2002 until 2008. She was one of the live-in girlfriends that appeared on the show “Girls Next Door.” Since her time dating Hefner, Marquardt has started the podcast “Ghost Magnet” and is engaged to long-time boyfriend Nick Carpenter.

Kendra Wilkinson

Kendra Wilkinson dated Hugh Hefner from 2004 until 2008.

Kendra Wilkinson dated Hugh Hefner from 2004 until 2008.
(Getty Images)

Wilkinson began dating Hefner in 2004, shortly after the two met. They ended their relationship in 2008, and Wilkinson left the Playboy mansion in 2009. Wilkinson went on to marry Hank Baskett, but the two have since divorced.

She works in real estate and was hired by the luxury agency The Agency.

Kristina and Karissa Shannon

Kristina and Karissa were the second set of twins to live in the Playboy mansion. The pair dated Hefner from 2008 until 2010 and appeared on “Girls Next Door.” After their time with Hefner, Kristina and Karissa went on to appear in other reality shows, including “Celebrity Big Brother” and “Rob & Chyna.”

The two also run a salon in Beverly Hills called GLAM.


Crystal Harris

Crystal Harris was married to Hugh Hefner from 2012 until his death in 2017.

Crystal Harris was married to Hugh Hefner from 2012 until his death in 2017.
(Charley Gallay/Getty Images for Playboy)

Harris was married to Hefner from 2012 until his death in 2017. Since Hefner’s death, Harris has spent time creating a lifestyle and travel blog. She also designed swimwear and was a DJ.

Harris recently responded to Madison, letting her know that she had destroyed alleged photos. Harris has also been candid about her marriage to Hefner, speaking to Fox News Digital in 2018.

“He taught me love. He taught me kindness. He gave me life. He really did,” she gushed at the time.


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