Here's What Hugh Hefner's Exes Are Up To Today

"I'm the boy who dreamed the dream," Hugh Hefner often said, as reported by The New York Times. If that dream was to date as many women as possible, sometimes several at once, Hefner did more than just dream it — he did it. The founder of Playboy Magazine, Hefner lived what many might cite as an ideal life. He owned an enormous mansion in Los Angeles, traveled the world on a private jet, had famous friends, and was always next to a beautiful woman.

But some of those beautiful women don't look at their time with Hefner rosily. Through memoirs, podcasts, and interviews with major publications, many of Hefner's ex-girlfriends have criticized the former Playboy publisher for his treatment of the women in his orbit, labeling him as a narcissist and a predator. Others, though, have staunchly defended their ex-boyfriend, highlighting his kindness and generosity. What the ladies all have in common is that Playboy is no longer the force in their lives that it once was — they've all moved on to other things. Here's what Hugh Hefner's exes are up to today.

Audiences were first introduced to Kristina and Karissa Shannon in 2008 via "The Girls Next Door." The Clearwater, Florida natives moved into the Playboy Mansion that October, and by June of 2009, they were officially Playmates. The twins posed in the magazine together, and in an interview with the Tampa Bay Times, they expressed their excitement over being featured in the magazine. They even sang Hugh Hefner's praises at the time. "He's fun. He's nice, really laid-back. He's all about having fun. Everyone gets along with him. He's very, very smart," Kristina told the Florida publication.

As the Shannon twins would document later, life at the Mansion for Kristina and Karissa wasn't fun for long. Kristina and Karissa appeared in the A&E documentary series "Secrets of Playboy" and noted that when they agreed to move into the Mansion, neither believed that Hefner was having sex with all of the women who lived with him. The Shannon twins claimed that on the night of their 19th birthday, Hefner gave them each a pill and forced them to perform sexual acts they were not comfortable with. "After that night, I didn't feel like my body was mine anymore. Like, I felt used, disgusted," Kristina said, as reported by People. In 2010, two years and many traumas later, the Shannon twins moved out of the Mansion.

Sondra Theodore was involved with Hugh Hefner for many years. The model first met Hefner when she was 19 years old, and by July of 1977, at 20 years old, she was named Playmate of the Month. Theodore lived at the Playboy Mansion for over five years, much of which she spent trying to pursue an acting career. While Theodore did find some acting work while living at the Mansion, as she claims, much of her efforts were derailed by Hefner. Instead, she says, her time was spent partying at the Mansion.

In 2022, Theodore shared stories from her time at the Mansion in the A&E docuseries "Secrets of Playboy," and she opened up further in an interview with Fox News. In the interview, Theodore claimed that she had tried to share her experiences for a decade, but that she couldn't find anybody willing to document it for her. The former actor detailed her memories of meeting Hefner, moving into the Mansion, and feeling that she had a real future with him. Theodore claimed that she and other women were given drugs and forced to have orgies with Hefner. "It's like I'm looking at somebody else's life ... I know it was me, but I'm still baffled by how he got me to twist my world so completely. And it was all for him," Theodore said of looking at photographs of herself with Hefner.

Lillian Müller was born in Norway and moved to the United States to further pursue a career in acting and modeling. Müller was named Playmate of the Year in 1976, and to date, she's been on the cover of Playboy nine times, more than any other model in the magazine's history. In her early days at Playboy, Müller also dated Hugh Hefner for a short time. Unlike some other ex-girlfriends, Müller stayed friends with Hefner, and she hasn't said anything negative about him since his death.

Now, Müller's main focus is educating others about living a healthy lifestyle. "I'm using sex appeal for a higher purpose now ... Those of us in the raw movement who are passionate about getting this message out are serving a power and energy much bigger than ourselves," Müller said in an interview with SarahBest. According to Müller's Instagram, in addition to modeling, she does speaking engagements, has written two books, and hosts a podcast.

Barbi Benton started dating Hugh Hefner in the late 1960s. After appearing on the show "Playboy After Dark," Benton started dating Hefner, and she had what would end up being one of the most massive influences on him of any of his girlfriends. It was Benton who convinced Hefner to purchase the Playboy Mansion. Benton eventually lived with Hefner in the Mansion, and she dated him until 1976, turning down four proposals from Hefner throughout their relationship. After leaving Hefner, Benton met another man, got married, and had children, but she always remained friends with Hefner, even appearing in multiple episodes of "The Girls Next Door."

Just before Hefner died in 2017, Benton visited her ex-boyfriend and longtime friend at the Mansion. "I went up to the Mansion, and rather than sit where other people were, he wanted to sit with me privately ... So we went to one of the rooms in the Mansion, and behind closed doors we had the most amazing conversation about old times," Benton said to People of her visit. Benton shared that Hefner had a cemetery plot beside Marilyn Monroe, and he was at peace about being laid to rest next to her.

Hef dated countless women, but he only ever married three times. He might have wed more, but he remained legally married to Kimberley Conrad, his second wife, for 30 years despite only being together for nine after their wedding. The couple got married in 1989 when Conrad was 26 and Hugh was 63, much to the surprise of Hefner's friends like Bill Cosby and James Caan. During their marriage, Conrad and Hefner had two children together, Cooper Hefner and Marston Hefner.

The year before Conrad married the Playboy publisher, she was featured on the cover of the magazine, and the same year she got married, she was named Playmate of the Year. In 2017, Conrad posed for the magazine again, this time recreating her 1988 cover in honor of Mother's Day, per her son Cooper's idea. "We decided to re-shoot a bunch of our old covers. I was sitting with my mom on Mother's Day and thought, 'Hey mom, do you want the opportunity to re-shoot your old cover?'" Cooper said in a video about the photoshoot, as reported by the Daily Mail.

Brande Roderick is another one of Hugh Hefner's former girlfriends who's defended him in the wake of controversy. After the A&E docuseries "Secrets of Playboy" aired in 2022, Roderick took to "Banfield" on NewsNation to defend the former Playboy publisher. "I learned grace from Hef, that's one thing that I learned and got to see firsthand is the way that this major iconic man, who's super famous, would react with everybody ... He was just so graceful, which is something you don't see a lot of times from celebrities in Hollywood," Roderick said.

Roderick and Hefner dated for about a year at the turn of the century. Roderick was named Playmate of the Year in 2001, and she went on to have a successful career in the entertainment industry. The model had roles in "Baywatch" in 2000, 2004's "Starsky & Hutch," and dozens of other projects throughout the past two decades, including 2022's "Twisted Vines." In 2021, Roderick got into producing, and her name has been attached to multiple projects over the past couple of years in that capacity, including the aforementioned "Twisted Vines."

In the early 2000s, Zoe Gregory was living in the U.K. on just £75 per week. Wanting to improve things for herself and her son, Gregory saved up to have a breast augmentation, and soon after she found herself topless in a British magazine. "It was always a dream to go to America or become a model, go to Hollywood. Page 3 opened the doors to that. I was doing glamour modelling and I was discovered by Hef, and started to do Playboy shoots," Gregory told the Daily Star. The next thing Gregory knew, she and her son were living in Los Angeles, her son at an apartment with a nanny and Gregory at the Playboy Mansion.

Now, most of Gregory's modeling is through OnlyFans, and she stays largely out of the spotlight. The model has been in the news some in the past few years, however, for various reasons. In 2019, Gregory alleged that she had received sexts from former Yankees player Alex Rodriguez less than a month before his engagement to Jennifer Lopez. Gregory also revealed what her time living at the Mansion was like, telling USA Today that she looks back on those years fondly.

Izabella St. James moved into the Playboy Mansion in 2002 and stayed as one of Hugh Hefner's seven girlfriends until 2004. St. James has been very forthcoming about her time at the Mansion, even detailing the reality of the famous grotto on the Mansion premises. "The heyday of the grotto's glory days was the '70s. That's when I think all the swinging or activities took place in the grotto," St. James told People in 2017. St. James opened up further in 2022 for the A&E docuseries "Secrets of Playboy." "[It was] the least sexual time I've had in my life. People have these grand visions of what takes place, and it's just not that. It was all very brief and a very pretty, nice illusion," St. James said of her time living with Hefner, as reported by USA Today.

St. James was open about her life with Playboy much earlier, too. In 2006, St. James released an e-book called "Bunny Tales," which shared more about her life at the Mansion. Now, St. James runs the non-profit organization she founded, The Pug Queen, which aims to rescue pugs living in dangerous situations like puppy mills or abusive homes.

Holly Madison is one of the most famous of Hugh Hefner's girlfriends. Madison began dating Hefner in 2001, and she stayed at the Playboy Mansion until 2008, gaining notoriety from starring in the E! Network reality show "The Girls Next Door." The show gave viewers access to the Mansion and its residents like never before, and fans became fond of Hefner's girlfriends, particularly Madison. After leaving the Mansion, Madison went on to marry, have children, and star in another reality show of her own. In recent years, Madison has re-emerged in the spotlight, sharing more from her time with the Playboy brand and becoming one of the most outspoken critics of Hefner.

One of the first avenues for Madison to share her perspective was through her 2016 book "Down the Rabbit Hole." Madison has also spoken out on multiple podcasts, both her own — "Girls Next Level," which she hosts with her former co-star and friend Bridget Marquardt — and others such as "Call Her Daddy." The former girlfriend also spoke out on an episode of "Secrets of Playboy" in 2022. In 2023, Madison's show "The Playboy Murders," which examines the murder cases of women who were somehow related to Playboy, aired, and it was renewed for a second season. "There were so many cases I'd never heard of, and I was so intrigued and wanted to learn more," Madison said to E! News of her work on the show.

Kendra Wilkinson was another one of Hugh Hefner's girlfriends who starred in "The Girls Next Door." Unlike some of her co-stars, Wilkinson remained on good terms with Hefner after she left the Playboy Mansion, and she used the famed grounds as the venue for her 2009 wedding to former NFL player Hank Baskett. Wilkinson and Baskett have since gotten divorced, but they had two children and their own reality shows, "Kendra" and "Kendra On Top," together before splitting up.

Now, as a single mom, Wilkinson's main priority is providing for her kids, which she does as a real estate agent. The former Mansion resident has documented her work in real estate through her Max reality series "Kendra Sells Hollywood." "​​I spend more time alone, focused on simple little ways to get better as a mom and business woman and it's not as glamorous as it used to be. To find who I am in the real estate world is so important and it's exciting to have this chance," Wilkinson said on Instagram of her current life and work.

Bridget Marquardt dated Hugh Hefner from 2005 to 2009. A star of "The Girls Next Door," Marquardt grew to fame alongside Holly Madison and Kendra Wilkinson, finding roles in films like "Scary Movie 4" and "The House Bunny" through her position with Playboy. After Marquardt left the Playboy Mansion, she began pursuing one of her passions more intently: ghosts. In 2011, Marquardt was on an episode of "Celebrity Ghost Stories," and a decade later, in 2021, Marquardt appeared on an episode of the show "Ghost Adventures."

Ghosts are still a large part of Marquardt's life. The former model hosts a podcast called "Ghost Magnet with Bridget Marquardt," and in 2021, she shared that she believes she was visited by Hefner's ghost in a dream. Marquardt said she felt Hefner's presence and could smell him, detailing that their dream meeting was at the Playboy Mansion. "I didn't get to say goodbye to him. I didn't like that. I tried to go up and say goodbye to him and I wasn't able to. And I feel like it was just sort of our goodbye and it felt like, it really did feel like closure. It really did feel like I saw him," Marquardt said to E! News of her encounter.

Crystal Hefner (née Harris) became a Playmate in 2009, and the following year, she was engaged to Hugh Hefner. Though Crystal and Hef broke up once before marrying, they officially tied the knot in 2012. Crystal stayed at the Playboy Mansion with Hugh until he died in 2017.

Now, the last of Hefner's wives is preparing to release "Only Say Good Things: Surviving Playboy and Finding Myself," her memoir about the time she spent with Hugh at the Mansion. "There are hard stories and people that have hurt me, and they're in there. The stories are very detailed, and there are things that have never been spoken about before," Crystal told Us Weekly about the contents of the book. In addition to writing her memoir, Crystal has been occupying her time as a real estate agent, and in December 2023, the former Playboy model launched a podcast, "Beneath The Surface With Crystal Hefner." "If you've ever been in a situation where people try to mold you into someone you're not but you did it anyway, it was like that," Crystal said of her life at the Playboy Mansion in the first episode of her podcast.