Now when I first put this list together, I simply wrote down a collection of things that I wanted to experience. Some things tested me physically, some mentally and there were a whole lot that I threw myself at without knowing what the test would be. Generally though they were all related by the fact that each item fascinated me in a certain way and filled me with the idea of possibility. The Playboy Mansion fitted this bill perfectly.

Now I’m happy to admit that on face value, this item is one of the more superficial on the list, but at the end of the day, why not? Goals are allowed to be superficial at times, I think!  The driver here was simple, I just wanted to fulfill a childhood dream of walking upon the hallow turf of a place so exclusive and bizarre that it acts as a home to a bevy of beautiful women who wear bunny ears all day and one extremely lucky man who dresses in a robe.

“Seb I hear you’re in LA on April 30th? I’m getting you in the Playboy Mansion”

The email I received from an anonymous person whilst traveling in the US was one I replied to immediately. Several exchanges later and I received another one that I admit made me smile with anticipation;

“Confirmed! Arrive at the Mansion gates and ask for a security guard called The Rock. Once they let you in, I’ve arranged for playmate Deanna Brooks to meet you and give you a personal tour of the Playboy Mansion. Enjoy and let me know how it goes”

I wish I could say that I worked harder for this invite but this was as hard as  it got. All I had to do was turn up. Number 89- Visit the Playboy Mansion was about to become a reality.

One thing that I love about kids is that they wear their emotions on their faces for all to see. If they’re sad; they present their big bottom lip with an accompanying frown. If they’re confused; they’ll stare vacantly back at you with an open mouth and when they’re excited they’ll sport a ridiculously large smile and giggle loudly. As I drove up to the gates of the Playboy Mansion, I must have looked like the latter. I couldn’t help giggling!

Talking to a voice through an intercom, I sat at the front gates nervously wondering what life was like beyond the gates, and after announcing my name whilst trying to sound calm, the gates slowly opened,  revealing a long driveway winding through a well kept and lush garden. After driving slowly with anticipation, the first sign I saw was wedged into a bush half way up the driveway. It read, ‘Playmates at Play’. Just as I imagined!

A further few twists and turns up the driveway and the lush gardens opened up to a huge old manor house, in front of which sat a beautiful water fountain acting as a turning circle for cars. Quietly I hoped that they might also act as some kind splash pool for playing bunnies. This was it, the Playboy Mansion.

The first thing to recognize here is the beauty of the place. Modeled on an Scottish manor house, the whole grounds are immaculately kept. Huge trees lined the various gardens and green grass basks in the sunlight as I curiously looked around one more time for playing bunnies. Nothing. With that a buxom lady opens the front door to the mansion and walked over towards me.

“Sebastian?”

“Yes!” I replied, slightly louder than anticipated.

“I’m Deanna Brooks and i’m so glad you could make it. Welcome to the Playboy Mansion”

Deanna Brooks was a Playmate a few years back. A beautiful and petite lady fitting the mould of what is expected of a Playmate, she also immediately came across as intelligent and funny.

Deanna shook my hand and explained how she was excited to take me around the grounds whilst sharing with me the ins and outs of the place. Not knowing too much about the Mansion or the lifestyle that came with it, I was surprised to hear that there was a zoo, an avery, as well as a few scattered building with themed rooms, around the grounds. The one thing that didn’t surprise me though was mention of a place they call ‘The Grotto’. Based in an underwater cavern, rumours have it, the Grotto plays host to many Playboy after partys, where swimwear and civilised behavior are both optional. This I was looking forward to see!

Allowing time on her own birthday to show me around the grounds, Deanna was doing me a huge favor, and before long we were strolling around the grounds very informally as we spoke about stories of the Mansion and the amazing man behind it all; Hugh Hefner, or Hef. Dating as many girls at one time as most men could hope for in a lifetime, Hef’s life seemed to be one moulded around his love of art, appreciation of beauty and fondness for fun. As we entered a quaint games room hidden in a far corner of the grounds, a series of Playboy pin-ball machines sat next to a well used pool table and an array of Playboy memorabilia adorned all around the room. This room played host to recreational time for Hugh, his bunnies and his guests. Deanna tells many a story, each one involving a celebrity of one sort or another who has become a friend of the mansion over time. Bill Cosby, John Lennon, and even Jimmy Conners made their way here often. Jimmy Conners excuse was that the Mansion also had a tennis court. Clever boy.

In what is somewhat of a misconception, the mansion itself is not a place full of TV cameras, pillow fights and drama. In fact it’s simply a house where people live their lives (consistent with his reputation, Deanna explained that Hef’s wardrobe is full of pyjamas). Poker nights on a Thursday, Boys night on a Wednesday, and even a Movie night on Sundays. Sure there is a zoo (which holds about 80 monkeys, rare birds and some incredible looking fish), but Hef and his girls all live here as one big family. This atmosphere is something that I felt everywhere. As strange as it may sound, the whole place feels quite homely.

Deanna, who after showing me an intricately mirrored room with padded flooring, a handy shower and velvet finish (if only the walls could talk!), then took me over to the zoo where she was clearly eager to introduce me to some of her old friends. Coco the recently widowed monkey, Inca the big billed Tucan, and a host of fish all welcoming our every move within a series of jungle-themed areas seemed to recognize Deanna’s face instantly. For the next thirty minutes I simply followed as she made sure to say hello to all of her mates who she knew from the days when she lived at the mansion herself.

Soon after walking a circuit around the house, being sure to peak through most windows of the private main building as Deanna points out Hef’s art collection, video room and poker lounge, we’re stopped in our steps by a flock of extravagant peacocks all of whom are hanging around a giant trampoline towards the back of the mansion. The fact that it’s mating season makes me laugh as we fittingly walk through their flirtatious behavior towards a huge swimming pool accessorized with a central rock landscape and a few waterfalls to fit. It’s stunning.

“So Sebastian, this is where we have a lot of fun; in the pool!”

This makes perfect sense and after dipping my toe in the water, I notice a small cave like opening at one end of the pool. A waterfall gushes over the entrance adding to it’s subtlety and as I gaze towards it, trying to see inside, Deanna delivers the great news;

“And this, Sebastian, is the Grotto. You know you’ve made it if you make it in here”

Of all of the stories that you may hear about the Playboy Mansion, they all seem to somehow involve the Grotto. For this reason, I simply had to see it.

Beckoning me in with the knowledge of a seasoned veteran, Deanna walked us past the cave entrance and through a secret doorway to the side of the rock face that allows us to stay dry. Flicking a few light switches on the way in, I entered the Grotto with a great big smile- like everything else in the place; it was amazing. A congregation of small Jacuzzi style rock pools all linked with one another, sparkle  brightly thanks to an array of underwater mood lights, giving the room the feel of a pirate’s caves full of treasure. The privacy of the grotto is alluring and only supports the nature of the activities that have become folk law in this great room.

Running in-between all the jaccuzis is a central body of water which links the front and back exits of the grotto- a subtle getaway route for those trying to remain anonymous at night. Deanna shares some more stories, insinuating that things other than conversation take place here on occasions. Childlike, I find it hard holding back one question that I’ve had in my head all day and without meaning to blurt it out;

“Can I jump in the water, Deanna?!”

Smiling back, the answer is positive.

“Sure, I won’t tell anyone”

Thirty seconds later, realizing that I don’t have any swimwear, I’m forced to think on my feet. There is only one option; nudity. Apologizing to Deanna in advance, I dart behind a large rock only to reappear shortly after, springing somewhat unelegantly into a particularly shallow jaccuzzi, bubbling ferociously. Laughter fills the grotto as I take a seat and take in the moment- I’m naked in the Grotto! This could not get any better.

“Where you’re sitting is actually Hef’s favorite seat.”

I’m not sure that the image of sitting in the very same place that Hef’s buttocks have occupied was a good thing or not, but i was going to have to get over this quickly- as Deanna then points out;

“Congratulations, you’ve now been with many naked people have been before”

Laughing together, I subconcioulsy wonder whether there are showers near by.

Now I’d be lying to you if I said that I didn’t spend the next twenty minutes frolicking around the Grotto (even completing a cheeky lap of the outside pool in full view of a few startled gardeners), smiling with joy with every stroke, but it was the last part of this day that I remember the most. Feeling completely at home with the sweet Deanna, the idea of this unique tour had been forgotten and dismissing time, we found ourselves sat in the depths of the Grotto, having a conversation on the meaning of life, self-fulfillment and what was on her list. The fact that I was sitting naked in Hef’s chair just made it even better.

It was in this moment that i wished her happy birthday and realized that I’d ticked off one of the stranger items from the list; Number 89- Visit the Playboy Mansion: TICK!

Something that rings true throughout my trip is the generosity of people. I truly believe that people everywhere have the capacity to help another, but it’s often finding an avenue to help that stops the most from achieving this. In this case of being given an opportunity to visit the mansion, I can’t thank Mr Anonymous enough for his selfless offer. The funny thing though is that the bigger picture here has nothing to do with bunny ears, robes or hidden caves, instead these things are just a cover to what is the really important message; people helping people. Everyone has goals, and alone we can certainly throw ourselves at something at full pace, but just as important as this is the idea of community and helping others.This is what my own journey of 100 Things has led me to realize. Connecting with people and spreading the spirit of generosity, support and community is crucial.

It resonates with one of the final things that Deanna tells me. Even though every year, 12 new playmates are taken on board by Hef, the connection is often life long. This is evident as Deanna explains that she crashed at the Mansion the night before after sharing a few too many birthday drinks with Hef. While sharing some of the great experiences she’s had from being involved with Playboy, Deanna shares that one of her favorite experiences was recently attending the Carnival in Rio with Hef’s son and several other Playmates. Playboy is a community.

I always get asked what item i’m next ticking off on my list, and certainly my mind is focused on this constantly, but just as much of my time now is committed to forwarding on and multiplying all of the generosity that I have felt on this journey so far.

What a day! There are big things ahead I think.

100 Things… What’s on your list?