Why did Holly Madison and Kendra Wilkinson split with Hugh Hefner? Truth behind Playboy founder's dating life

While Holly left the mansion on a bitter note, Kendra left on a very happy note


                            Why did Holly Madison and Kendra Wilkinson split with Hugh Hefner? Truth behind Playboy founder's dating life
Kendra Wilkinson dated Playboy founder Hugh Hefner while he was still dating Holly Madison (Getty Images)

Back in the day E!'s hit reality show 'The Girls Next Door' gave the world a peek into the glamorous and glitzy lifestyle of the Playboy Mansion residents Holly Madison, Kendra Wilkinson and Bridget Marquardt. We all got to see a glimpse of how these three women spent their time inside the famous mansion and their life as the girlfriends of Playboy founder Hugh Hefner. 

Although it's been over a decade since the show's final episode aired, there still seems to be a lot of drama and tension among Hefner's girlfriends. On April 7, Holly made an appearance on the 'Call Her Daddy' podcast. She discussed her current relationship with her former co-stars Bridget and Kendra. While she had nothing but kind words for Bridget, she also revealed that she had no relationship with Kendra. The 41-year-old then went on to discuss her romance with Hefner and declared that she was glad that they never had children. Read on to know more about why Holly and Kendra split up from Hefner and eventually moved on with their lives.

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Playmate Holly Madison was only 21 when she moved into Playboy mansion with Hugh Hefner (Photo by Frederick M. Brown/Getty Images)

Why did Holly Madison break up with Hugh Hefner?

At the age of 21, Holly moved into the Playboy Mansion after being a frequent visitor for over a year. The Oregon native who was once Playboy magazine's fan ended up becoming the founder's girlfriend. To the outside world, it appeared like the couple were very happy. Holly was so smitten by Hefner that she was keen on marrying the adult magazine mogul and start a family with him.

Unfortunately for her, Hefner reportedly told her that he wasn't keen on marrying the third time and also the couple had difficulty having a baby. She eventually broke up with him in 2008 and moved out of the mansion. At that time, Hefner released a statement saying, "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."

Publisher Hugh Hefner and girlfriend Holly Madison flash outside The Standard Hotel on September 24, 2003. (Photo by David Klein/Getty Images)

After leaving the mansion, Holly married her longtime boyfriend Pasquale Rotella in 2013 and had two children with him. While she was still married to Rotella, Holy released an explosive memoir, 'Down the Rabbit Hole', in which she shared shocking details of her life inside the mansion. She shared details of her first night with Hefner in graphic detail. "Two huge television screens projecting graphic porn lit up the otherwise dark bed. 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 wrote. She described sex with Hefner as 'boring basic sex'.

On the podcast she also explained how looking back on her life she was glad that she never had any children with Hefner. "I knew it was because of him. I was healthy. He was just too old. 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."

Playboy's Hugh Hefner (R) and girlfriend Playmate Kendra Wilkinson met when she was 18 and he was 78 (Photo by Michael Buckner/Getty Images for AFI)

Why did Kendra Wilkinson and Hugh Hefner Split?

While Holly left the mansion on a bitter note, Kendra left on a high note. Kendra was only 18 when she first met Hefner at his 74th birthday party. Shortly after that they met up and hit it off instantly. Hefner wasted no time in asking her to move in with him into the mansion. In an interview, she revealed that she moved in with Hefner because she wanted to get away from her then-living situation. She said, "He asked me to be one of his girlfriends and I was like, "I don’t know what that means, but hell yeah I’m there. I was living in the smallest apartment with the ugliest **** and I was praying for anything to get me out of there. He asked me to be part of the Playboy Mansion and I accepted, of course. I went by straight away but I didn't know that sex was involved."

She also claimed that she used to be really 'drunk' or 'smoke lots of weed' before sleeping with him. "I was usually very drunk doing those evenings, I tended not to care about much until the next day. I had to be very drunk or smoke lots of weed to survive those nights. At about the minute mark, I pulled away and it was done. It was like a job. Clock in, clock out. It’s not like I enjoyed having sex with him," the Daily Mail reported. 

Kendra eventually left the mansion in 2008, after her then-boyfriend Hank Baskett, a wide receiver for Philadelphia Eagles proposed to her. She married him in 2009. The couple shares two children together. They divorced in 2013.

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