Of the many women to come in and out of Hugh Hefner's life, Holly Madison is one of the most famous.
The late magazine mogul's girlfriend of seven years was a prominent fixture in his life for nearly a decade. Having frequently visited his infamous Playboy Mansion while a 20-year-old college student in Los Angeles, the aspiring actress—who would go on to become a bestselling author—decided to move into his house a year later in 2001. (According to Holly, during their first date, "he was literally pushed on top of me.")
Their untraditional relationship was chronicled on E!'s series, The Girls Next Door, with Holly the ever-doting and loyal wife figure, alongside co-stars and fellow girlfriends Kendra Wilkinson and Bridget Marquardt. Not surprisingly, their dynamics were unique.
But it's been more than a decade since the reality TV series premiered and all three women have moved on from their Playboy days. Earlier this year, Holly shared where she stands with her former co-stars on an episode of Call Her Daddy.
"Bridget and I have always been close," Holly revealed. "We've always been friends since day one. She is [the sweetest]."
However, when asked if she has a relationship with Kendra, the Down the Rabbit Hole author put things simply, "No."
Holly also opened up about her romance with the Playboy founder, where she explained just how grateful she was for never getting pregnant. Although, she admitted they had "boring basic sex."
"I knew it was because of him. I was healthy. He was just too old," the star, turning 42 Dec. 23, said about the reason they never had kids. "When I had first gotten into that situation and something happened in my mind that first night I had sex where I felt like, 'Ok I did that. I like breached my own boundaries and I wasn't comfortable with it. Now I have to make this situation into something.' I almost locked myself into this box."
As fans of Girls Next Door might recall, Holly expressed her desire to not only marry Hugh, but to start a family. Ultimately, the his refusal to wed for the third time and his inability to procreate was considered their breaking point. She called it quits in 2008.
"Holly wanted very much to get married and have children and that wasn't in the cards for us," Hugh shared in a video for Playboy at the time. "I made a noble effort on the children's part of it. I was not prepared at this point to marry again."
However, he eventually did. Following his breakup with Holly, he began dating twins Kristina and Karissa Shannon and, later, Crystal Harris. In December 2010, he proposed to Crystal.
"I'm very surprised," Holly told E! News at the time of their engagement. "I have a lot of different feelings on it. I don't just feel one way. I kind of didn't want to put a generic statement out there like 'Congratulations!' because I felt everyone would see through that."
The eternal bachelor didn't have a smooth trip down the aisle however. Though his Playboy Playmate bride unexpectedly broke off their engagement five days before their vows, the two ultimately tied the knot in December 2012.
Holly would go on to marry longtime Pasquale Rotella in 2013. In 2018, just weeks before celebrating their fifth wedding anniversary, they filed for divorce. They share two kids together, Rainbow Aurora Rotella, 8, and son Forest Leonardo Antonio Rotella, 5.
But during her marriage, and time without any contact from Hugh, Holly shed new light on her former life when she published her memoir, Down the Rabbit Hole. In the no holds barred book, she shared her own controversial account of her time at the infamous property.
In print, Holly, who initially was under the impression the women did not actually have sex with Hugh, recalled her first night with him in vivid detail. "Two huge television screens projecting graphic porn lit up the otherwise dark bed," she wrote. "In the middle, a very pale man was tending to his own business (if you're catching my thinly veiled innuendo) and puffing on a joint before passing it around to the nearest blonde. The girlfriends, in various stages of undress, were sitting in a semicircle at the edge of the bed — some kneeling, some standing, some lying down."
She claimed he offered her a Quaalude, alleged the orgy-esque activity would take place twice a week. She also alleged that he disapproved of her short haircut and called her "old, hard and cheap" when she wore red lipstick.
According to Holly, the women at the mansion were also expected to abide by a curfew, and that he fostered competition among the women. "I tricked myself into thinking I had feelings for Hef," she wrote in the book. "He had this gentlemanly veneer, he was intelligent, and I loved watching old movies with him. I focused on the positive things, not the negative."
However, after suffering depression, suicidal thoughts, and—according to her—Hugh's accusations of infidelity, the two broke up.
With Kendra at his defense, Hugh responded to his ex's allegations, suggesting that Holly was seeking fame with her memoir.
"Over the course of my life I've had more than my fair share of romantic relationships with wonderful women. Many moved on to live happy, healthy and productive lives, and I'm pleased to say remain dear friends today. Sadly, there are a few who have chosen to rewrite history in an attempt to stay in the spotlight," he told E! News in a statement at the time. "I guess, as the old saying goes: You can't win 'em all!"
While the two had their differing accounts of how their relationship played out, Holly wanted the public to know that she was in a much better place in her life.
"For so many years, I just wanted to move forward with positivity, only say nice things. I wanted to stand on my own two feet, start from scratch, just be me, not talk about Hef," she previously told E! News. "But, I would get so many people coming up to me saying, 'Don't you miss the mansion?' or 'I'm sorry Hef didn't marry you' and I'd see everything that was written about me and people think they know me just because the know one side of me from the TV show, which was seven years ago…and I just didn't think overall it was a very good message for women because the best part of my life has been the seven years since I've left the mansion."
(This story was originally published on Thursday, Sept. 28, 2017 at 1:09 a.m. PST)