Hugh Hefner’s Former ‘No.1 Girlfriend’ Reveals What Life Was Really Like Inside Playboy Mansion

by : UNILAD on : 01 Oct 2017 15:27

Following the death of Hugh Hefner this week, an array of stories from the world of Playboy has cast a shadow over the late entrepreneur.

‘Hef’, as he was commonly referred to, was considered the ‘Godfather of Sex’ – a man who had a vision for bountiful free love, except it turns out, it wasn’t as liberating as perhaps most of us thought.


The glamorous ‘dream-life’ Mr Hefner painted for the public, seemed to come at a price, particularly if you were one of his ‘chosen bunnies’.


Hef’s former ‘Girlfriend Number One’, Holly Madison, described her life at the infamous Playboy Mansion as some sort of ‘bedazzled, twisted, toxic prison’.

Holly spent six years of her life as partner to a man old enough to be her grandfather, writing:


How could I justify such a thing? ‘I’m here for adventure, a once-in-a-lifetime experience. I’m here as a stepping-stone to something else,’ I told myself.

And then perhaps the biggest illusion of all: ‘I’m here for love.’

Holly released her book, Down The Rabbit Hole in 2015 – it was, as the book states:

Curious Adventures and Cautionary Tales of a Former Playboy Bunny.


Despite many people saying the ‘bunnies’ knew what they were getting into and talking about them in a derogatory manner, Holly revealed how it really felt to be shacked up with the King of Playboy and how sex, for her, was never on the agenda.

In the book Holly relives how her Playboy days came about:

I was a small-town girl who dreamt of becoming someone special.

I moved to Los Angeles to go to college and got a job waitressing at a Hooters Bar – a job that resulted in an invitation to a party at the Playboy Mansion.

For a starstruck girl from Oregon, this felt like the chance of a lifetime.

The dress code was strict: ‘Sleepwear Required.’

☀️ Saturday #relaxingbythepool #newsuit #summerlove #mystyle

A post shared by Holly Madison (@hollymadison) on


Holly continued:

When I arrived with my friend Heather, every inch of the estate seemed to sparkle.

I was flattered to be one of 20 or so girls invited to the smaller Sunday pool parties.

When the light dipped below the hills, the festivities moved inside.

Eventually, his harem of girlfriends would trickle down to take their seats next to Hef at the dining table – I could never understand their lack of enthusiasm.

Initially, I assumed they were spoiled, jaded, or just not a good fit in Hef’s world.

This may sound naïve, but I didn’t immediately realise that they were actually required to sleep with him.

So excited I got my splits back today! @suwasit #splits #stillgotit #flexible #keeptrying

A post shared by Holly Madison (@hollymadison) on

Holly said her main focus was a career in acting and believed Playboy would help her in reaching her goal:


My main focus was pursuing an acting career, but it’s almost unsettling how quickly your priorities can shift.

The desire to perform is what had first driven me to Los Angeles and, as the lease on my apartment neared its end, the thought of returning home almost killed me.

I started to wonder, couldn’t Playboy help me reach that goal?

The more time I spent there, the whole girlfriend thing began to look appealing.


Holly recalled one particular evening where she was even offered drugs by the sex-obsessed senior:

Back at the table, he leaned towards me with a bunch of large horse pills in his hands.

‘Would you like a Quaalude? Hef asked. ‘No thanks,’ I answered cheerfully. ‘I don’t do drugs.’

‘That’s good, he said nonchalantly. ‘Usually I don’t approve, but in the Seventies they used to call these pills “thigh openers”.’

Today, I want to scream ‘PAUSE!’ and freeze frame that moment in late August 2001. I want to grab that young girl, shake her and demand: ‘What the hell are you thinking?’ Why didn’t I run for the nearest exit?

I suppose I had already made up my mind at that point. If I became a girlfriend, I would have somewhere to live. If I became part of Playboy’s inner circle, perhaps that could help my career?


The Playboy bunnies were extremely good at portraying their individual happiness – whether it was real or not.

Numerous appearances and photo shoots always showed them as bright eyed, with wide smiles, but according to Holly, this was the opposite of how she and some of the others living at the mansion felt:

There was a strict routine. There were many rules.

First, there was a curfew – Hef required his girlfriends to be in by 9pm and we were not allowed to fraternise with the staff.

Each girlfriend was given a weekly clothing allowance of $1,000 and the last major requirement was that girlfriends attend all Hef’s events.

PA Images

Holly continues:

I was too naïve to realise it at the time, but Hef wanted to have us wallowing in our own insecurities and pawing for his acceptance.

Girlfriends that didn’t get along gave him the feeling of being fought over and desired, something he was desperate to feel in his old age.

I’d always been confident, but it didn’t take long for my self-worth to start to crumble.

He was cruelly manipulative, happy to reduce me to tears. ‘Don’t ever wear red lipstick again,’ he once warned me in a low voice. ‘You look old, hard, and cheap.’

Google Earth

Holly’s health even began to suffer through living in this way:

I was so constantly on edge that I eventually developed a stammer so I tried as best I could to stay quiet.

To Hef, this was a sign of submission that helped me become one of his favourites and I developed my own brand of Stockholm syndrome, identifying with my captor.

It didn’t seem to matter that I couldn’t recall how or why.

In less than a year, Hef had promoted me to his ‘main’ girlfriend – there was nothing ceremonial: Hef simply asked if I wanted to move in-to his room. That was it.

No promises were made; no token jewellery given. The only difference was that he often said ‘I love you’, and started referring to me as the ‘love of his life’.

Who's ready to party? #Day2 #latergram #Coachella #GhostlyOrbs #DrunkOrbs [email protected]

A post shared by Holly Madison (@hollymadison) on

I guess all that glitters isn’t gold.

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Holly Madison
  1. Holly Madison

    Down The Rabbit Hole