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It’s Hugh Hefner’s 100th Birthday—What Do His Exes Look Like Now?

The legendary Playboy founder dated countless women and married three. This is what they’re up to as of 2026.

Roosa RahkonenReporter, The Looker

PublishedApr 9, 2026, 5:18 PM EDT

UpdatedApr 9, 2026, 9:54 PM EDT

Updated Apr 9, 2026, 9:54 PM EDTPublished Apr 9, 2026, 5:18 PM EDT

“This was going to be my wedding day, but life is full of surprises. After all is said and done, staying single is probably for the best,” Hugh Hefner wrote in a 2011 tweet.

The Playboy founder, then 85, posted it after Crystal Harris, then 25, left him less than a week before the pair was to be married.

Hugh Hefner would turn 100 on April 9. Despite his proclaimed affinity for singledom, Hefner infamously dated a long list of women and was married to three of them before his 2017 death at age 91.

While his biggest legacy is undoubtedly the magazine he started in Chicago in 1953 and grew into a risqué empire, the women at Hef’s side throughout his 60-plus years in the spotlight continue to capture public attention.

Here’s where the media mogul’s ex-girlfriends and ex-wives are now.

Kimberley Conrad, 63

In 1989, at 63, Hefner married 26-year-old Playmate of the Year Kimberley Conrad.

The couple had two sons: Marston in 1990 and Cooper in 1991. Conrad and Hefner separated in 1998, though they stayed close: She moved with their two sons into a luxurious $7 million house next door to the Playboy Mansion in the exclusive Holmby Hills neighborhood in Los Angeles. The couple finalized their divorce in 2010.

Conrad has since shied away from the spotlight, though in 2024, she released a statement defending the late Playboy founder after Hefner’s widow, Crystal Harris, published a memoir that painted him in a bad light.

“I’m speaking out now for the first time about Hef because I feel compelled to speak on behalf of someone I love, who is no longer here to speak for himself,” the statement read.

“We should be wary of those who try to destroy things because they are no longer benefiting from them,” it continued. “People like that will never hold credibility, in my opinion. If you want to talk about exploitation, this is exactly what these women have done with Hef in his later years and at the end of his life.”

Mildred “Millie” Williams

Hefner married his first wife, Chicago native Mildred “Millie” Williams, in 1949—four years before he founded Playboy, which published its first issue in December 1953.

The two were classmates at Northwestern University, and welcomed two children, including Christie (in 1952) and David (in 1955), before their marriage ended in 1959.

In December 2025, Williams died at 99. Her daughter, Christie, provided a heartwarming description of her beloved mother in an obituary published by the Chicago Tribune.

“My mom was my biggest cheerleader and inspiration, and a joy to be with,” Christie said. “She was smart and funny and full of life until the very end.”

Holly Madison, 47

Holly Madison was one of Hefner’s more well-known partners. In 2001, at just 21 years old, Madison moved into the Playboy Mansion and became one of Hefner’s girlfriends. She announced the breakup and moved out in 2008.

She starred in the first five seasons of the reality show The Girls Next Door, which aired from 2005 to 2010 and centered on life at the Playboy Mansion.

In 2023, she told People that her time living with Hefner negatively affected her self-esteem.

“I would definitely say that living in the mansion created a body dysmorphia for me because I was always kind of wondering what’s wrong with me,” she said.

“Hugh had a way of making me feel like I wasn’t pretty enough, and I would look around to everybody else and constantly be wondering, what’s so different about them and why are they so much better?” she said, adding that had she stayed longer, she might have turned into a “plastic surgery nightmare.”

Now 47, Madison, a mother of two with her ex-husband, businessman Pasquale Rotella, showcases her life—including cosmetic procedures—on social media.

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She has published two memoirs, Down the Rabbit Hole in 2015 and The Vegas Diaries in 2016, and hosts two podcasts.

On You Wish, she interviews famous women about their lives, and on Girls Next Level, she delves behind the scenes of her time at the Playboy mansion together with her co-host, fellow The Girls Next Door star Bridget Marquardt.

She is also the host and executive producer of Discovery’s The Playboy Murders, a true-crime TV show that explores murder cases involving Playboy models and playmates.

Bridget Marquardt, 52

Before becoming an official girlfriend and starring in The Girls Next Door, Bridget Marquardt had multiple unsuccessful Playboy auditions. But her persistence paid off: at 29, she moved into the Playboy Mansion in 2002.

In 2009, she posed nude in Playboy with Madison and Kendra Wilkinson to promote their final season of The Girls Next Door, and exited the mansion shortly after.

Now 52, Marquardt hosts two podcasts: Girls Next Level, co-hosted with Holly Madison, and the paranormal podcast Ghost Bunny.

Kendra Wilkinson, 40

Kendra Wilkinson moved into the Playboy mansion after she met Hefner at his 78th birthday party in 2004. She was just 18, but soon became one of the stars of The Girls Next Door alongside Madison and Marquardt.

After leaving the mansion in 2009 to start a life with NFL wide receiver Hank Baskett, Wilkinson went on to star in multiple reality shows. The two married in 2009 and welcomed two children, but eventually filed for divorce in 2019.

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In 2024, Wilkinson reflected to People on her time at the Mansion, saying she was “dumb” when she made the “crazy” choice to live with Hefner.

“I got into deep regret [afterward]. I got to that point where I started hating myself. ‘Why did I have sex with Hugh Hefner?’ I hated my boobs, my body, my face. I got to that point where I started hating myself,” she said.

But now, the realtor is doing well, describing herself as a “balanced, single, positive, fun woman who loves life.”

In an Instagram post, she responded to online critics who were writing that she has “aged poorly.”

She wrote, “For some reason, I’m happier than I’ve ever been lately even with a little weight gain and wrinkles and I’m not going to tie my happiness again into the negative energy.”

In late March, she shared that she was starting a weight loss journey with GLP-1 medication. “I don’t really want to be skinny, but I just want to be balanced and fit in my jeans again,” she explained.

Crystal Harris, 39

Crystal Harris was the star of the sixth and last season of The Girls Next Door from 2009 to 2010.

She began dating the Playboy founder, who was 60 years her senior, in 2009. The couple got engaged in 2010, but Harris called off their wedding in 2011, five days before the ceremony, prompting Hefner’s tweet.

The couple later reconciled, and they married on New Year’s Eve in 2012. Harris remained married to Hefner until his passing in 2017.

Harris revealed on Facebook that she had undergone explant surgery after her breast implants “slowly poisoned” her in 2016. She suffered from symptoms such as fatigue that was “so severe that [she] could barely leave the house or drive.”

In 2024, Harris released her bombshell memoir, Only Say Good Things: Surviving Playboy and Finding Myself, detailing her time at the mansion.

On April 2, the best-selling author eloped with James Ward.

Karissa and Kristina Shannon, 36

Twin sisters Karissa and Kristina Shannon were stars of the sixth and final season of The Girls Next Door, starring alongside Harris. They moved into the Playboy Mansion in 2008, when they were 18, after a successful test shoot with the magazine.

The duo starred in two consecutive centerfolds together and were named Miss July and Miss August in 2009 before they moved out of Hugh’s house in 2010.

In 2025, they told People that life at the Playboy Mansion was not easy.

”We got a lot of jealousy from the other Playmates because we were twins,“ Kristina said. ”We were the first twins to each get our own months, which made Playboy history. We were the youngest Playmates and the youngest girlfriends.”

Life after the Mansion was also difficult for the pair, she said.

“We gained weight. There was alcohol and pills,” Kristina said. “We were really unhealthy and lost and, even at points, suicidal. We had no one. It was just us, trying to figure it out after losing ourselves.”

The two left Los Angeles but, in 2025, revealed they were ready to be back. They considered different career paths, from podcasting to reality TV, but said they were in the process of getting their real estate licenses.

The twins were considering some aesthetic changes, too: ”We do believe in Botox and some fillers, but we’re reducing our breast implants," Karissa told People. “We’re changing our look. This is our transition in our thirties and you can see it. We’re just trying to figure it out like everybody.”

Roosa RahkonenReporter, The Looker

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