Life as a Playboy bunny wasn’t always easy! Holly Madison and Kendra Wilkinson’s relationship 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.”
Along with Bridget Marquardt, the trio became known as more than just Hefner’s girlfriends as E! cameras went behind the walls of the mansion for The Girls Next Door. 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.
As a result, season 6 included Hefner’s new ladies, Crystal Hefner (née Harris) and twins 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: