Kendra Wilkinson Shares Her One Regret Living at Playboy Mansion
Kendra Wilkinson wishes she had hopped into the real estate business sooner.
After all, the Playboy model turned realtor said she likely lost out on potential celebrity clients during her time as one of Hugh Hefner's girlfriends.
"The only thing I can say I regret in my life is not starting my real estate career while I was living at the Playboy Mansion," Kendra told Fox News on June 3. "What was a thinking? I was surrounded by everyone—every celebrity, every billionaire."
But that's not to say she had a bad time, either. As the 40-year-old put it during a recent episode of the Skinny Confidential podcast, "It was like heaven."
"It was a heavenly experience for me," she continued. "There couldn’t have been a better experience.”
While Kendra did have some "bad experiences when it comes to the business side of things," she said her relationship with Hugh—who died in 2017 at age 91—had always been "awesome."
"He was a generous, nice person," Kendra shared. "I don’t see him in any other way."
The Kendra on Top alum moved out of the Playboy Mansion in 2009 after meeting NFL star Hank Baskett. They married in the same year, but called it quits in 2018 after welcoming son Hank Baskett IV, 15, and daughter Alijah Baskett, 11.
However, her former Girls Next Door costar Holly Madison cannot say the same thing about Hugh, who she dated from 2001 to 2008.
"After I left the relationship, I was so shell shocked because I realized that this vision I'd had of him the whole time as this amazing person was just something I had wished for and made up in my own head," Holly told E! News in 2023. "And I realized the person I was looking at was really a stranger."
Though she did have a unique connection with Hugh, Holly said she "knew there were problems in the relationship the whole time."
"He had been causing all this drama between me and the other girls," she added. "I couldn't put up with it anymore."
Keep reading to find out where all the Girls Next Door stars landed after leaving the Playboy Mansion.
Kendra Wilkinson was one of Playboy founder Hugh Hefner's three live-in girlfriends when the show premiered in 2005. Fans were so invested in Wilkinson that she got her own spin-off show, Kendra, on E! after leaving the series in 2009.
Her subsequent WE tv series, Kendra On Top, which followed her journey as a mother of two, son Hank IV (born Sept. 11, 2009) and daughter Alijah (May 16, 2014), and her marriage to NFL player Hank Baskett, who she swapped vows with at the Playboy Mansion on June 27, 2009.
The couple split up in 2018 and their divorce was finalized the following year. In 2021, Kendra got a real estate license and launched her own Discovery+ series, Kendra Sells Hollywood.
From investigating the mansion's possible haunted past to planning Hef's birthday, Bridget was No. 1. Her skin was ready to be shown on the Travel Channel's Bridget's Sexiest Beaches and she had cameos in the likes of Entourage, The House Bunny and Curb Your Enthusiasm.
Bridget's interest in the paranormal has come full circle as host of the podcast Ghost Bunny, featuring interviews with celebs who've experienced the unexplainable and other deep dives into various unsolved mysteries with the help of experts. She also began hosting the Girls Next Level podcast with Holly Madison in 2022.
Once part of an iconic trio, she happily paired off long ago with partner Nicholas Carpenter.
Holly Madison had a successful career after her tenure at the Playboy Mansion, including competing on Dancing with the Stars before getting her own show, Holly's World, that centered around her career in Las Vegas, including her Peepshow residency.
She published a revealing memoir about her time in the Playboy Mansion, Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny, in 2015, chasing that it with 2016's The Vegas Diaries: Romance, Rolling the Dice and the Road to Reinvention.
The longtime PETA advocate is mom to daughter Rainbow (March 5, 2013) and son Forest (Aug. 7, 2016) with ex-husband Pasquale Rotella.
In addition to participating in the scathing A&E docuseries Secrets of Playboy, she described having a complicated relationship with her Girl Next Door costars on a 2021 episode of the podcast Call Her Daddy. "Bridget and I have always been close," she said. "We've always been friends since day one. She is [the sweetest]." When asked if she had a relationship with Kendra, Holly tersely replied, "No."
Indeed, Holly proves her and Bridget's bond each week on the Girls Next Level podcast.
While all of the ladies of The Girls Next Door had a special place in Hefner's heart, Crystal Harris actually married the Playboy mogul in 2012, the then-86-year-old's third trip down the aisle. They remained together until his death in 2017.
After Holly spoke out about her relationship with her costars, Crystal was quick to pick a side. "I was at the mansion for a DECADE almost four years ago now and these ladies and their drama were there years before that," she wrote on her MeWe account. "So much time has passed. I side with Kendra here."
"Not sure why these women who shared an incredibly uncommon and rare experience (that will never be repeated in our lifetimes) can't get along?" she continued. "Maybe for the same reasons Holly and Bridget despise me for absolutely NO reason. I hope one day we can all get along and compare experiences."
Crystal also became an advocate for Lyme disease awareness after announcing she'd been diagnosed with the illness in 2016.
In 2024, she debuted her relationship with Jim Ward and announced she would be reverting back to using her maiden name after going by Crystal Hefner following her 2012 nuptials.
"I'm in a much better place," Crystal told E! News, seven years after Hugh's death. "Next step is definitely going back to my original last name and finally taking that last step to just be myself."
After the first generation of The Girls Next Door girlfriends left, twins Kristina Shannon and Karissa Shannon moved into the Playboy Mansion in 2009. During the remaining seasons, they celebrated their Playboy Summer Issue in Vegas, went camping in the backyard with Hef and prepared for bit parts in Sofia Coppola's Chateau Marmont-set movie Somewhere.
After the show wrapped, Kristina and Karissa joined the ninth season of Celebrity Big Brother and opened a beauty salon in Los Angeles.
However, the sisters eventually moved to Ann Arbor, Mich.
"Kristina and I decided to move,” Karissa told People in 2025. “We didn't know where to go, so we decided to go back to where we were born and leave L.A."
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