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Hugh Hefner's former girlfriends are on bad terms now, but back in 2008, Kendra Wilkinson had nothing but nice things to say about The Girls Next Door mansion-mate Holly Madison. After Madison went through a difficult breakup with illusionist Criss Angel, the younger playmate told PEOPLE that she only wanted the best for Madison. "[Holly] has so much love to give someone. I hope that she finds someone to give her that love back ... I hope she stays happy and strong, and I hope she finds someone that loves her for who she is – for her heart."
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At the time, Madison was equally supportive of her former costar, frequently gushing about how happy she was to watch Wilkinson marry now-former NFL player Hank Baskett. "Ever since they met, I've just seen a difference in Kendra. She's matured; she's a more compassionate, considerate person," Madison told PEOPLE shortly after Wilkinson announced her engagement in 2008. "She's just grown up so much, and just to see what he brings out in her is just amazing." (Madison was a bridesmaid in the wedding, which Wilkinson later admitted she regrets).
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Hefner's former No. 1 girlfriend was also elated to see Wilkinson settle down with Baskett and start a family. In 2008, she gushed about how she couldn't wait to meet Wilkinson's new addition. "I was surprised but so happy for her. I know that ever since she met Hank, she's been anxious to have a baby. She'll be really in tune with that baby, and she'll be a great mom."
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Signs of a rift in their relationship started appearing back in 2010 when Wilkinson revealed to PEOPLE that she considers Hugh Hefner to be one of her closest friends. "I can tell you that Hef is my closest friend. I'm not just saying that. He makes sure he writes to us every chance," she said. "He's always thinking about us, and that's a real friend." However, she made no mention of either Madison or their other housemate, Bridget Marquardt.
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Still, they seemed to be on friendly terms throughout Wilkinson's time on Dancing with the Stars. When Madison first took to the dance floor in 2009, Wilkinson frequently posted messages of support, and when it was Wilkinson's turn in 2011, Madison returned the favor.
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After not speaking about each other for four years, Madison finally revealed how she really felt about Wilkinson in her 2015 memoir Down the Rabbit Hole. In it, Madison admitted that her friendship with Wilkinson ended after she talked about them to the tabloids. "For someone who was all of a sudden trying to act like she was better than Bridget and me, she sure wasn't above using us for publicity when she needed it," Madison wrote, adding, "I don't miss her."
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Madison's book also revealed that Wilkinson got on her bad side when they first met back in 2004 and the younger girlfriend demanded "the biggest room" upon moving into the Playboy Mansion. Still, she mentioned that she admired Wilkinson's "sense of entitlement" and "hustler mentality."
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After Madison's revelations about life in the mansion went viral, Wilkinson fought back, defending Hefner – and throwing a little shade of her own. "Holly, you can tell, had this ulterior motive every minute being at the mansion, and that motive was – it was clear as day – she wanted Hef's kids. She wanted a piece of Playboy, and she wanted to marry Hef for, obviously, his will," she told PEOPLE.
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And it doesn't look like these two will be hanging together back at the mansion any time soon. In June 2015, Wilkinson revealed to PEOPLE that she regrets her one-time friendship with Madison and, in hindsight, believes that any affection between the two of them was just for show. "I don't ever want to have a relationship with Holly again," Wilkinson said. "And I made a mistake by thinking what we had was real."