Life as a
Playboy bunny wasn’t always easy! and Holly Madison ’s relationship Kendra Wilkinson has been rocky since they lived in the Playboy Mansion during their respective relationships with Hugh Hefner.
Madison, for her part, began seeing Hefner in 2001 after she attended one of the weekly pool parties at the mansion. The former Alaska resident detailed her decision to move into the house in her 2015 memoir,
Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny.
“I thought I was an adult and thought I was making my free choice. And I was. But I wasn’t sophisticated or really prepared. And kind of got in over my head,” she wrote. “I could understand how people thought it was strange. But I guess I wasn’t comfortable enough to explain why I thought it would be fun or why I thought it would be a good idea.”
Wilkinson, meanwhile, worked Hefner’s 78th birthday party in 2004 and moved in soon after.
“Hef asked me to be one of his girlfriends, and live in the mansion and I was like, ‘Hell yeah, I’m here!’” she recalled on
I’m a Celebrity, Get Me Out of Here! in 2014. “I was living in this small-ass apartment with this ugly-ass bitch. I was praying for anything to get me out of there. … I moved in and weeks went by and I didn’t know that sex was involved. I knew nothing about Playboy, I’d just graduated high school.”
, the trio became k Bridget Marquardt nown as more than just Hefner’s girlfriends as E! cameras went behind the walls of the mansion for . The reality series premiered in August 2005 and ran for five seasons with Madison, Marquardt and Wilkinson as the stars. While the three women appeared on the sixth and final season, their romantic relationships with Hefner ended in 2008. The Girls Next Door
As a result, season 6 included Hefner’s new ladies,
(née Harris) and twins Crystal Hefner Kristina and Karissa Shannon.
While Madison and Wilkinson appeared to be on good terms during and after
Girls Next Door, it didn’t take long for relationship to crumble.
“At the end of the day, it’s a very awkward situation ’cause it’s not like we’re The Spice Girls,” Wilkinson said on Fox 5’s
Good Day New York in 2015. “We dated an 80-year-old man at the same time. It’s very awkward. She probably wants to distance herself from that situation. God bless her, she should. It’s embarrassing because I saw some things that she probably doesn’t want me to talk about.”
Scroll through for a timeline of their feud:
Madison alleged in her 2015 memoir that their relationship with Wilkinson, who moved in the mansion three years after the
Holly’s World alum, was rocky from the start.
“Despite my attempts to befriend Kendra, she continued to push me away,” she wrote. “Hungry from her own ‘team,’ Kendra desperately tried to make each new Playmate who arrived at the mansion her friend — and her friend alone.”
Madison continued: “At 19 years old, Kendra was stuck with a 9 p.m. curfew, a 78-year-old boyfriend, and a stricter set of rules than she had ever had at home. And now, adding insult to injury, she was finally realizing that she wasn’t as special as Hef made her believe. She was just another blond girlfriend — and life at the mansion wasn’t all she imagined it to be.”
Filming Girls Next Door starting in 2006
The Girls Next Door, Madison, Wilkinson and Marquardt appeared to be friendly.
When Wilkinson walked down the aisle in 2009, Madison and Marquardt were bridesmaids at the nuptials.
In addition to Wilkinson and Madison making cameos on each other’s reality TV spinoffs,
Kendra and Holly’s World, respectively, the Peepshow star publicly supported Wilkinson on Dancing With the Stars in 2011.
During a 2012 interview with CNN, Wilkinson said she was “never even really friends” with Madison or Marquardt. “We’re different,” she added at the time.
Down the Rabbit Hole, she fired back, calling Wilkinson “the fakest person [she’d] ever met.”
“Kendra had apparently given an interview to a tabloid explaining that she wasn’t friends with either of us as if she were somehow better than everyone else,” Madison wrote in 2015. “Of course, I wasn’t going to stoop to her level and address this only on social media, so I decided to text her how I truly felt: that she was a coward and that she tried to act like the ‘real’ girl on TV, but she’s the fakest person I’ve ever met — and that if she had a problem with me, she should have confronted me like an adult instead of just going silent.”
She concluded: ”After that, I deleted her number from my phone. Kendra and I haven’t spoken since, and I have to say, I don’t miss her.”
In an interview with
Us Weekly at the time, Wilkinson slammed the book, telling Us, “It’s a shame that someone can’t be appreciative of what something like that has given them.”
As Madison geared up to release her second book, T
he Vegas Diaries: Romance, Rolling the Dice and the Road to Reinvention, Wilkinson took to Twitter.
“Now Holly is on cover of
People mag sayin she lived in fear at the mansion,” she wrote in a series of since-deleted tweets in May 2016. “She wasn’t in fear with that d–k in her ass for a paycheck. That bitch is in fear now knowing so many of us saw her doing some nasty s–t. She’s embarrassed and in shame. She was the clean up girl … Hollys job was to get Hef hard again and clean him up with her mouth.”
Wilkinson later apologized: “I know my recent posts were a little over the top and I apologize for that. Sticking up for me n my beliefs is hard for me at times. Sorry.”
Madison, meanwhile, fired back in a statement to
Us: “I’ve written a book, The Vegas Diaries, that’s about letting go and moving on. About resolving the past so you can live a future. I’ve dealt with my demons and I’ve come out ahead. I can hold my head high and work hard to be the classy and kind person I aspire to be. I want no part of a one-sided argument or feud where one woman lives to demoralize and degrade another woman. For those with unresolved issues, therapy works. You should try it.”
As the feud made headlines, Wilkinson said she was just trying to stand up for Hefner.
“I am being truthful,” she said on SiriusXM radio at the time. “It’s what I saw constantly all the time … [Holly] wants to make you, like, ‘Oh, I didn’t do that. I never did that! Look away, look away!’ But I’m saying, ‘Dude, you’re no better than I am.’ … She should refund Hef.”
reignited her feud with Wilkinson during an appearance on the “Call Her Daddy” podcast in April 2021. When asked about Wilkinson’s claim that she didn’t have sex with Hefner, who died in 2017, before she moved into the mansion, Madison said she was lying.
“I had to sleep with him first,” Madison told
Alex Cooper. ”I’m not trying to slut-shame anybody or anything, but nobody ever got asked to move in unless they had slept with him.”
The real estate agent, meanwhile, fired back via Instagram, writing “Dude… it’s 2021 😂. Times have changed. I forgive and have kids to love and focus on.”
After one person asked Wilkinson why she’s “always hating” on Madison, she responded, “How am I hating. She’s [the] one out there. I’m all love now baby.”
When another social media user sked her to try to see Madison’s side, Wilkinson added, “OK if you believe this will help women then I will try to understand. I wish I had more time with Holly to understand this side … I wish her the best in life and this helps heal her.”