Hugh Hefner & Holly Madison’s History: Everything To Know About Their Romance & Her Accusations

The ‘Girls Next Door’ alum was one of the ‘Playboy’ founder’s girlfriends for seven years, but Holly has since revealed some of the darker aspects of being a ‘Playboy’ model.

Holly Madison rose to fame as a model for the famous Playboy magazine. The now-42-year-old blonde beauty became a reality star in 2003, when she was one of the three featured ladies on the series The Girls Next Door, which followed Holly, Bridget Marquardt, and Kendra Wilkinson in their lives at the Playboy Mansion along with the magazine’s founder Hugh Hefner. Holly was known as Hugh’s number one girlfriend during her time in the mansion, and the two dated from 2001 until 2008. Since the split, Holly has come forward with many accusations against Hugh, and she’s revealed that her relationship with the late founder, who died in 2017, wasn’t as sweet as it may have seemed on TV. Find out more about Holly and Hugh’s relationship, and the accusations she’s made against him since splitting up, here.

When did Holly and Hugh meet?

Holly visited the Playboy Mansion a number times throughout college. After having spent much of her young adulthood in the mansion, she decided to move in when she was 21 in 2001. While she was working as a model for the suntan oil Hawaiian Tropic, Holly said she got her first invite to a party at the Playboy Mansion, where she first said hello to Hugh.

Holly’s opened up about why she originally decided to move to the mansion in her memoir Down The Rabbit Hole, which came out in 2015. She admitted to feeling like she was in a “desperate situation” during an April 2021 interview with the podcast Call Her Daddy. During the interview, she alleged that Hugh offered her quaaludes, and she was “wasted,” when they first had sex. She said that she was shocked after their first time having sex, because she noticed other girls with Hugh during her first night out with him. “When I got up there, I was so wasted and thrown into it, that once it was done, there was something about the experience that made me feel very out of control,” she said at the time.

Holly also recounted her first night out with Hugh as one of his girlfriends during a December 2021 interview on the Power: Hugh Hefner podcast. She said she expected the night out to be more like a “first date” and said he was “literally pushed on top of me,” when she wasn’t planning on having sex with him.

Shortly after the two started dating, Holly said that she felt “trapped” by some of the mansion’s rules and Hugh’s personal preferences for her. In the years since they’ve split, Holly had admitted to asking Hugh if she could tryout to be a Playboy Playmate, and he would “hold it out of reach” and let various girlfriends try out for it. She alleged that Hugh “flipped out” at her, after she cut her hair short, in an interview as part of the A&E docu-series Secrets of Playboy. “He was screaming at me and said it made me look old, hard and cheap,” she said.

‘The Girls Next Door’

Holly admitted to thinking she’d only live in the mansion for about a year tops, during the Power interview, but she became well-known as one of Hugh’s featured girlfriends on the reality show The Girls Next Door in 2003, two years after moving in. She was regarded as the Playboy publisher’s number one girl. The show ran for six seasons, and Holly appeared in 80 episodes. The show not only showed the lives of the girls surrounding Playboy events, but it also gave an in-depth look to Holly’s relationship with Hugh.

The model revealed that after she learned about the show, she was “annoyed,” because she wasn’t cast as the “ambitious” girl in the Power interview. Holly also explained that she thought that the show would also help her get into the magazine. In some episodes, she admitted to how she wanted to be in the magazine, and how she was disappointed that she was to see other girls come and try out to be Playmates. “He had known for years that we wanted [to be in the magazine], and he very deliberately kept it away from us, and I think, very much enjoyed making us think that we weren’t good enough,” she said in the podcast.

During their time on the show, she became a junior photo editor for Playboy, and she had great things to say about the position, and the show also shifted the dynamics in their relationship. “He wasn’t trying to date other people or sleep with other people, and we weren’t going out to clubs, and we weren’t doing the bedroom thing,” she said on Power. “I felt like his attitude toward me really changed, and he really did start to care for me.”

In the years since the show has ended, Holly has admitted to some of the difficult things she was struggling with behind-the-scenes, both on her own and with Hugh. She admitted to feelings of body dysmorphia, and a strong desire to lose weight, in a July 2021 TikTok video.

Holly and Hugh Break Up In 2008

After seven years together, Holly ended her relationship with Hugh in October 2008. Hugh alleged that the two had broken up, because they didn’t have plans for marriage or children in a 2008 interview with The Associated Press. “If Holly says it’s over, I guess it’s over,” he said at the time, while saying that Holly was still living in the mansion, but staying in a different room. After the breakup, she announced she still planned to work with Bridget and Kendra, and she appeared in four episodes of the of the last season of Girls Next Door, before she produced the spin-off Holly’s World.

After Holly and Hugh split, the Playboy publisher did get engaged (and later married) to the model Crystal Harris. After their engagement was made public, Holly admitted to feeling “surprised” at the news. “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,” she told E! News at the time.

Holly’s accusations since the breakup

In the years since the breakup, Holly has shed tons of light onto the darker aspects of living in the mansion. She opened up about wanting to “drown herself” while she lived in the mansion as part of the Secrets of Playboy series. “I remember there was a point in time a couple of years in. After we had gone out and after we had all been in the bedroom. Everybody’s leaving and walking out, and I was in the bathtub. And I just wanted to drown myself. I just felt like I was in this cycle of misery,” she claimed. Even after the breakup, Holly was still a junior photo editor for Playboy until 2009, which she quit after not finding the job “challenging,” via E! News. 

She’s also pushed back on the narrative that Hugh was a “good guy” or “nice man.” She’s called her relationship with Hugh “abusive” and said that he’d commonly practiced love-bombing (or being overly-affectionate early on in a relationship). “The reason I think the mansion was very cult-like looking back on it is because we were all kind of gaslit,” she said as part of the A&E docu-series.

After the breakup

Long after the breakup, Holly eventually married Insomniac Events founder Pasquale Rotella in 2014, and the pair had two children: Rainbow Aurora, 8, and Forest Leonado Antonio, 1. Unfortunately, Holly’s marriage to Pasquale wasn’t meant to be, and the two divorced in 2018. Hugh married his third and final wife Crystal Harris in 2012, and the two were married until the Playboy founder died at age 91 in September 2017.