Whenever you mess around with Hugh Hefner, you're messing around with everyone Hef's fooled around with, and that number is by no means small. Hef doesn't wear protection during his bedroom "parties" and doesn't really care whether or not his girlfriends get tested, so if someone has a communicable disease, everyone has it. That's the reason Hef's main girlfriend gets to go first because that's when it's "safest" for her.
The Playboy life isn't all that easy for every Bunny. Even the "successful" Bunnies, like Holly Madison who was chosen to be Hef's number one girlfriend, still feel the stress of the position. In her memoir, Holly reveals that she turned to alcohol and other substances to help with the depression and anxiety she experienced as Hef's main girlfriend. "The depths of my own depression had led me down this very dark path, and there was no gleaming light, however distant, at the end of this tunnel. Maybe it was the alcohol, but drowning myself seemed a logical way to escape the ridiculous life I was leading."
A Playboy Bunny, especially one who also had the honor of being one of Hef's girlfriends, had to follow a very strict schedule, or at least that's what we learned from former girlfriend Holly Madison's memoir, "Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny,". Remember, Hef was a very old man and like many other old people, he liked to keep a tight schedule. Every night of the week except for Thursday had its own event that the girls had to make an appearance at or face Hef's disappointment.
There was Fun-In-The-Sun Sunday, where Hef threw a pool party and later held a movie screening in the Mansion's movie theater. Monday was Manly-Night when Hef would invite his friends over for dinner and a card game. On Family-Night Tuesdays, Hugh's sons and ex-wife would come over to visit. Wednesday was the night that Hef took the girls out to a nightclub to show them off. Later that night, they had their little bedroom ritual. Friday went along the same lines as Wednesday, while Saturday was Movie-Night when Hef would screen a recently released movie or watched one of his favorite old classics.
When Bunnies take up Hef's offer to live in the Mansion, they aren't allowed to have a regular 9-5 gig. Other than their weekly allowance, the only other way for a Bunny to make money is to put in paid appearances at nightclubs, festivals, and other such events. In her book, "Sliding Into Home," Kendra Wilkinson, who found fame thanks to her appearance on the E! show The Girls Next Door, explained, "I hate putting my hand out, but we couldn't have jobs other than getting appearance fees." Even though being a Bunny freed up their time, it wasn't like they could really utilize that time to focus on furthering a different career.
Nowadays, the Bunnies living in the Mansion get an even rougher deal. They no longer receive the weekly allowance and they're still not allowed to get a day job. All they get is the bragging rights and free room and board. Even the Playmate of the Year got a downgrade. It used to be that the Playmate of the Year got a free Porsche, now they only get a Mini Cooper that they only get to keep for a year. The economy has apparently hit Playboy very hard.
Every Friday morning, the girls would line up and go to Hef's room to collect their weekly allowance. First, according to Izabella St. James, one of Hef's former girlfriends and author of the memoir, "Bunny Tales: Behind Closed Doors at the Playboy Mansion," they got down to business as fast as possible. "Life was so unstable at the Mansion that we always felt that we had to get [the allowance] right then, because we did not know if we would be there tomorrow." They all waited for the moment Hef went to the safe on his bookshelf and counted out $1,000 in crisp $100 bills. Although the girls made sure to get to Hef's room bright and early for this weekly tradition, none of them liked having to do it.
"We all hated this process. Hef would always use the occasion to bring up anything he wasn't happy about in the relationship. Most of the complaints were about the lack of harmony among the girlfriends --- or your lack of ... participation in the 'parties' he held in his bedroom. If we'd been out of town for any reason and missed one of the official 'going out' nights [when Hefner liked to parade his girls at nightclubs] he wouldn't want to give us the allowance. He used it as a weapon." It's almost like if your boss didn't give you your paycheck until he'd chewed you out about petty office matters in front of all of your coworkers. Oh yeah, and your boss is also your lover. That's not too awkward, now is it?
The Playboy Mansion isn't nearly as glamorous as they'd like you to believe. While the girls all get their own rooms which they can decorate as they please, the rooms are still kinda shabby at best. The furniture in the rooms is all mismatched as if it had been purchased from a resale shop, but that wasn't the worst part. Izabella recalled her old room from her time as Hef's girlfriend saying, "Although we all did our best to decorate our rooms and make them homely, the mattresses on our beds were disgusting -- old, worn and stained. The sheets were past their best, too. Eventually, I persuaded Hef to pay for a new mattress and bed linen, but I had to turn in every single receipt before I was reimbursed." That's a lot to go through just to have somewhere clean to sleep at night.
Although it may seem like a free-for-all from the outside, there's definitely an order to Hugh Hefner's madness. He usually likes to keep three to 15 official girlfriends in the Playboy Mansion at all times, but he picks only one of them to be his number one girlfriend. She's the one who gets to share Hef's bed every night. The other ladies have their own rooms and only go to Hef's when it's time to get freaky or to pick up their weekly allowance. Right now, the top dog is Crystal Hefner, his wife who is a whopping 60 years younger than him. Since shortly before their engagement, Hef has been apparently faithful to his new bride.
The bedroom's not the only place to go to see who's top dog among the Bunnies. Which table the girls sit at during meals is also a good indication of their standing with Hef. Melissa Howe, a one-time Bunny, told Mirror, "There are three dining tables. In one room is Hef's top table where everyone wants to sit, then the family table which is second best. But in another room beside the kitchen is the table for the more lowly guests, the nobodies and the girls who've annoyed him. Hef decides the seating plan every day and no one wants to end up on that third table." Staying in Hef's favor definitely has its upside. You always get the best of everything, but only if you behave exactly how Hef wanted you to.
A free and freaky lifestyle is what young Bunnies are promised when they start out, but many of them end up chaffing against all the rules they're expected to follow as long as they live in the Playboy Mansion. If a Bunny breaks the rules, they're definitely going to hear about it. Speaking to the Mirror, Melissa Howe said, "If you do something wrong, you'll get an email. There's a strict code of conduct. There are even rules about Instagram and Twitter. You've got to show everything in a good light and if you're drunk in a picture you'll be in trouble."
Kendra Wilkinson revealed that the staff kept detailed notes on when the Bunnies left the house and what time they returned. Hef would go over the logs every morning, apparently to make sure that the girls were following the house rules. "It was way more strict than my parents had ever been," she said. Maybe their 9 p.m. curfew has a little something to do with the girls feeling like they're back to living with their parents. That almost sounds like the girls are back in high school again! Totally get why some of the Bunnies found the constant scrutiny totally unbearable.
In her memoir about her time as one of Hugh Hefner's girlfriends, "Bunny Tales: Behind Closed Doors at the Playboy Mansion," Izabella went on in detail about the disgusting state of the carpet. According to her, the carpets were already in disrepair when she began her tenure as one of Hef's favorite Bunnies. "Hef did not care about our carpets: the one in his bedroom had not been changed for years. It was literally the color of diarrhea."
Things didn't really get better when Holly Madison became Hef's number one girl and moved into Hef's room with her pooches. "It became significantly worse when Holly moved in with her first dog and then got another," Izabella continued. "The dogs were not housebroken and relieved themselves on the carpet. Many a late night or early morning we stepped in her dog's pee, or worse, poop." It didn't help matters that Hef insisted on white carpet for the girls' rooms, which looked nice at first, but after the dogs, foot traffic, and spills, it became a nasty, dingy grey.
You might expect a bit of drama and fighting in a house that's mostly occupied by beautiful, vain women, but you probably wouldn't expect a man like Hugh Hefner to be the main cause of it. According to Holly Madison's tell-all memoir, Hef loved stirring up drama between the ladies. It apparently made him feel desirable to have all these hot, young women fight over him. "I learned Hef was the manipulator and that he pitted us against one another," she wrote in her book. "There were always different political alliances with the girls. Hef liked to play the main girlfriend off the youngest one to try to create competition." In a house full of mean girls, somehow Hugh managed to be the meanest girl of all.
It should be pretty clear by now that when someone agrees to be one of Hugh Hefner's very special girlfriends, then there are some certain expectations about what they're willing to do. All of the former Bunnies agree that one of their most important duties was taking care of Hef's...needs. Every so often, Hef hosts a "party" in his room. Nowadays, the girls take turns pleasing him. They're allotted about two minutes each, with Hef's main girlfriend getting the first go-round. The other girls, who are either waiting their turn or just finished, sit around and basically cheer Hef and his current partner on.
One hopeful Playboy Bunny wannabe, Jill Spaulding, was invited to the Mansion on the night of one of Hef's infamous parties. Though she did not participate that night, or during the next party she attended, she was able to be a witness to a freaky affair. "If you kept your pajama bottoms on, that was a sign that you didn't want to have contact that night," she told Daily Mail. When Jill twice declined an invitation to join in, she said, "Hef looked absolutely furious, and one of the girls hissed at me that I was disappointing him. I didn't care. Hef's face was like thunder but I was left alone."
It's not easy to say no to a man like Hugh Hefner, who is certainly used to getting exactly what he wants from the women in his life. Still, at his age, bedroom activities are almost beyond him, so maybe this is all about his image rather than his actual wants. Past Bunnies all agree that the only reason why Hef is able to participate at all is purely because of help from pharmaceutical sources.
As we all know, Hugh definitely had a thing for blondes. More specifically, he preferred blondes with long hair with an innocent, girl-next-door look to them. In her book, Holly recalled the time that she got a makeover. She'd cut her long, blonde locks into a sleek bob and put on some red lipstick. She said that when Hef first saw her, he was very upset. "I hate the whole look. I hate the makeup and I hate the red lipstick." Hef told her, adding, "You look old, hard, and cheap."
Hef would also take pictures of himself with the girls before they left to go to the club. The next morning, he'd have the photos delivered to the girls. Some might think Hef just wanted to give the girls something to remember the night by, but Holly explained that the photos "only amplified the massive pressure to always look perfect and cause the girlfriends to spend hours critiquing their appearances." The Mansion doesn't really sound like it's the sort of place that would do wonders for a woman's self-esteem.
Michelle Braun, at one point, was probably the most feared woman in Hollywood. You won't find her in any films or TV shows, but she was very close to some of the most elite stars around. You might have heard her name connected with the likes of Tiger Woods and Charlie Sheen since she was the one who arranged for their escorts. She was also connected to Hugh Hefner, but not in a way that Hugh appreciated. Michelle claimed that one of Hef's girlfriends in the Mansion was actually one of her girls, placed there to recruit Playmates to come work for her in their off hours. Speaking with Page Six, she revealed, "I only worked with famous girls, mostly Playmates. Hef couldn't keep any of his girlfriends in the [Playboy] Mansion," she said. "At one time, seven of the eight girls living in the Mansion were working for me. I had one of his girlfriends in the Mansion just to recruit for me."
That really didn't sit well with Hef, especially after Michelle goofed and used a photo taken for Playboy to advertise one of the girls'services. Playboy ended up suing her for copyright infringement, a suit she eventually settled. According to Holly's memoir, the incident left Hef so shaken and suspicious that he demanded to check all of his girlfriends' passports to look for trips to Turkey, which is an escort hotbed. Anyone who'd recently been to Turkey was kicked out of the house. In the book, Holly claimed that she knew exactly which girl it was who secretly worked for Madam Michelle, but her lips are sealed.
Among the many rules for the ladies living in the Playboy Mansion was one very important one: no boys allowed. The Playmates weren't allowed to have "side boyfriends" or even invite men into the house. In fact, whenever they went out with Hef on their twice-weekly visit to the nightclub, they weren't allowed to speak to any men but Hef, and if they danced, they had to do so in front of his table where he could keep a close eye on them. Still, despite the rules and close scrutiny, some of the girls did manage to see other men. Kendra was one of them.
Only 23-years-old at the time, Kendra was the youngest of Hef's three girlfriends, and she wasn't above sneaking around to take care of her 'needs.' "I had to have [relations] every now and then, so I had to kind of sneak it," she confessed to US Weekly. "I swear on my two kids --- I never hooked up with one person in the mansion while being with Hef. I have that much respect. I would go to hotels down the street."
Though Bridget and Holly really were very close, and seem as if they're genuine friends even to this day, not everyone in the Mansion got along. Perhaps the most notable feud was the one between Kendra and Holly. In her book, Holly claimed that Kendra was "the fakest person" she'd ever met. Kendra clapped back in a Twitter tantrum she soon deleted, at one point claiming that Holly was "the cleanup girl," who was just afraid that the people who saw the "nasty" things she did in the Mansion would one day spill the details. Since then, both women have put the incident behind them.
Though the Playboy Mansion has a reputation of a place where anything can happen, the Bunnies actually didn't have all that much freedom. With the 9 p.m. curfew and the strict schedule they had to keep, for some of the Bunnies, the mansion was less a paradise and more a prison. By the end of her tenure at the Mansion, Holly Madison no longer looked at the mansion with rose-tinted glasses. In her book, she wrote, "Everyone thinks that the infamous metal gate was meant to keep people out. But I grew to feel it was meant to lock me in." Well, melodrama aside, Holly could leave anytime she wanted, but she would no longer have "Playmate" status, which comes with its own perks.