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A Detailed Look At Hugh Hefner And Holly Madison’s Complicated Relationship


Holly Madison was, for a long time, the number 1 girlfriend of the late magazine mogul, Hugh Hefner. The 91-year-old starred on the E! Series, The Girls Next Door, with his girlfriends, Kendra Wilkinson, Bridget Marquardt and Holly Madison. As a 20-year-old, Holly visited the lavish Playboy mansion and merely a year later she moved into the house in 2001.

During her seven years at the mansion, Holly was regularly regarded as the number one girlfriend.

Despite the pair’s complicated relationship, the couple appeared to be in love.

At the time, many thought Holly would be ‘the one’ for Hef but at that point in Holly’s life, she really wanted to get married and start a family.

However, it was Hef’s refusal to get married for a third time (he ended up getting married to Crystal Harris later in his life) and his inability to have kids that led to the couple separating in 2008.


In an interview with his own magazine, Playboy, at the time, Hef said: ‘Holly wanted very much to get married and have children and that wasn’t in the cards for us. I made a noble effort on the children’s part of it. I was not prepared at this point to marry again.’

But at that time, Holly was also experiencing suicidal thoughts as well as depression and that played a pivotal role in the pair’s split.


After leaving the mansion, Holly penned her own memoir, Down the Rabbit Hole where she delved deep into her and Hef’s complicated relationship.


In the book, Holly expressed her initial ideas that the women at the mansion wouldn’t have sex with Hef but in reality, the women were expected to engage in group activities.

Holly also wrote that Hef would have a curfew for all the women at the mansion and that he would regularly foster competition between his girlfriends.


In the book, she wrote: ‘I tricked myself into thinking I had feelings for Hef. 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.’


After the book came out, fellow housemate and former girlfriend of Hef, Kendra Wilkinson, came to his defense.

Daily MailDaily Mail

She alleged that Holly would ‘prance’ around the mansion as if she was the first lady and the publication of her book was simply a means for her to attain fame.


In an interview with E! News, Hef said: ‘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 they remain dear friends today.’


He continued: ‘sadly, there are a few who have chosen to rewrite history in an attempt to stay in the spotlight. I guess as the old saying goes: You can’t win ’em all!’


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