Dates rejected me for being a Playmate, but men who queue for Lily Phillips & Bonnie Blue are worse, says Holly Madison

The Sun

17-06-2025

HOLLY Madison was a 22-year-old girl when she became a playmate, thinking it would give her the chance to have a better life.
But now, aged 41, Holly has revealed the struggles she faced while dating to the Playboy mogul, who was 53 years her senior, Hugh Hefner.
4
4
4
Speaking on The Skinny Confidential podcast, Holly opened up about being rejected by men for being a playmate.
She revealed that after leaving the Playboy Mansion, men would approach her and want to date but would get 'jealous' of her past when things turned serious.
Holly explained: "There were a lot of people who wanted to date me, but I think in a very superficial way.
I think it was like, 'Oh, I want to date that hot girl on the Billboard right there and then tell my friends about it.'
"I would say the most challenging thing is that people would get together with me, knowing exactly what my history was, and then they would all of a sudden have a problem with it.
"After our relationship got serious, they'd get really jealous. They'd come up with all these imaginary scenarios in their heads about what could have possibly went on."
Despite the string of insecure and jealous men she dated, Holly says the men lining up to bed controversial OnlyFans creators Lily Phillips and Bonnie Blue are much worse as they chose to be intimate with them while staying anonymous.
Speaking on the topic with podcast hosts Michael and Lauryn, Holly agreed that the line of men also 'rattle her' as they choose to be anonymous instead of being open about sexual relations.
"I want to know what guys are in the Lily Phillips line, just kidding."
"All these guys, line up and they have ski masks on to partake, because they want to be anonymous," she added.
We lived in the 'glam' Playboy mansion as Hugh's girlfriends - we'd get 'replaced' if we were ever sick & the furniture looked like local charity shop buys
Mansion Madness
From the outside, being a Playmate looked glamorous - hanging with A-list celebrities and partying with your friends all day long.
But Holly said the reality was completely different and said it was a 'toxic' environment.
She said: "I feel like unfortunately mine is a lot of bad memories, especially in the first four years I lived there.
"It was just a hellhole. It was like none of the girls got along. It was super toxic."
Facts you didn't know about the Playboy Mansion
Girlfriends vs Playmates
Rumour has it that Hugh Hefner would have two to a dozen "girlfriends" living with him at a time. These girlfriends are not to be confused with Playmates. Each girlfriend had their own room, but one 'special lady' was named as girlfriend number one and stayed with Hef in his room. Each girlfriend received a $1,000 (£760) weekly bonus "allowance."
Hef's Wild side
The Playboy mansion was home to a private zoo. It was one of very few private residences that actually has a zoo license. Hefner was a fan of birds. Among his collection - many of which roamed the grounds - were peacocks, macaws, flamingos, toucans and ducks.
The Elvis Legend
Within the mansion was a secret room, called 'The Elvis Room.' Legend has it that the King himself, Elvis Presley, had a little slumber party in the room with up to eight eager bunnies.
In the past, Holly has said the girls would be fighting during the day and then sitting naked together at night.
She continued: "I can't explain to you how embarrassing that whole routine was, especially as we got later down the road when there was a lot of conflict with the other girls.
"You're literally sitting there naked having sex in front of a group of people who hate you and talk s**t about you while you're having sex," Holly said.
"I thought that we were going to be like BFFs and it was going to be so much fun and I thought that it was going to be like total slumber parties and like hanging out in each other's rooms and borrowing clothes and just like really fun," said Holly.
Speaking on her podcast, The Girls Next Door, with fellow Playmate Bridget Marquardt revealed the glam person of the house was nothing like reality.
In the early 2000s, Bridget recalled, the mansion ''was the place to be''.
''Everyone wanted to be there - every celebrity, every girl that I knew of wanted to be a part of it, wanted to be a Playmate, go to the parties.
''They had the best parties in the world there.
''It's the place that you wanted to go and you wanted to be seen, and you wanted to be a part of that whole lifestyle.''
But while the A-listers were living the high life, Hugh's girlfriends ''were required to sit at the table the whole time and ask if you needed to get up to go to the bathroom''.
She added: ''You could dance a little - but you were kind of greeting everybody [...], so we definitely didn't feel free.''
4
Top Grades
Those who had made it into the villa would also have Polaroids taken during the many star-studded bashes - which Hugh, who passed away at 91, would then grade from A to D.
''D - you're not invited back, C - you're maybe on the big party list, B - you're on all the party lists, A - you get invited to the pool parties and stuff like that,'' Holly revealed.
But the graded snaps, the pair said in a recent podcast, were the least of their worries.
Holly said: ''When I think about the worst thing, I just think about anything in the bedroom and just the fact that anyone would be invited in there.
''We didn't get to agree on who got to come in and who got to watch, and who got to do whatever - and it was just traumatising.'