Hugh Hefner, Holly Madison
Hugh Hefner (L) and his playmate ex-girlfriend Holly Madison (R), pictured May 25, 2006 celebrating his 80th birthday during the 59th Cannes Film Festival, don't appear to have ended their relationship on good terms. Getty Images

Holly Madison is one of Hugh Hefner's most notable ex-girlfriends. The former Playmate served as the publishing mogul's leading lady for the majority of their seven-year relationship, however their relationship ultimately deteriorated.

"Holly wanted very much to get married and have children and that wasn't in the cards for us," Hefner explained in a video for Playboy. "I made a noble effort on the children's part of it. I was not prepared at this point to marry again."

Madison has since made several damning comments about Hefner and the nature of their relationship.

Lack Of Intimacy During Sex

Madison detailed her sex life with Hefner in her book "Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny."

"There was zero intimacy involved," she wrote. "No kissing, nothing. It was so brief that I can't even recall what it felt like beyond having a heavy body on top of mine."

Alleged Mental and Emotional Abuse Occurred

While not directly referencing Madison, Hefner told E! in 2015 that "sadly there are a few who have chosen to rewrite history in an attempt to stay in the spotlight."

Madison later fired back during an interview with the Inside Edition the same year.

"I don't let him have emotional or mental control over me anymore — I let all that go," Madison said.

Hefner's Apparent Insecurities

Madison reportedly learned the hard way what lengths Hefner would go to in sparking drama between playmates. She told People in 2015, "I think he should really be more secure in himself."

Hefner Allegedly Offered Madison Prescription Drugs

Madison had attended a few parties at the Playboy mansion during her college years. The playmate alum, however, alleged that Hefner got Madison drunk and offered her prescription medication.

"The first night I went out with Hef and the girls, I got really drunk. He offered me prescription drugs, which I didn't take," Madison said on OWN's "Where Are They Now" in 2015. "He offers quaaludes to all the girls that would come out with him."

Living In Mansion Was 'Traumatic'

Since her departure from the Playboy Mansion, Madison has described her time there as "traumatic."

"It turned out to be something that was traumatic for me in a way that I wasn't really prepared for...I felt really ashamed of the choice I made," Madison said on OWN's "Where Are They Now" series.

Hefner Lack Of Knowledge Of Girlfriends

Madison claimed that Hefner didn't know much about his girlfriends. Hefner, however, allegedly managed to keep the girls in line by way of "favoritism." His favoritism method kept the girls "on their toes."

"He knew roughly four things about each girl," Madison wrote. "Her name, her age, where (approximately) she was from, and how well she behaved and followed the rules."

Beauty Expectations Were Made Known

Hefner made his desires for the playmate's fashion and beauty aesthetic "abundantly clear," according to Madison. She detailed in "Down the Rabbit Hole" that each girlfriend was given a $1000 weekly clothing allowance and unlimited beauty services, which included plastic surgery.

"I've always been very honest about it. I've had my boobs and my nose done," Madison said on E!'s "Good Work" in 2015.

Hefner's Selective Memory

Madison's second book, "The Vegas Diaries: Romance, Rolling the Dice, and the Road to Reinvention," detailed aspects of her strained relationship with Hefner.

"If Hef truly was confused as to why I left and forgot there was any fighting, he either had the world's most selective memory or thought talking down to his girlfriends and making them cry on a regular basis was normal," she wrote.

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