I Secretly Wish I Was A Gigolo (or is it Gigolette?)

You could build your entire future on it, if you’re good at it.

There are two reasons I’m writing about Gigolo-ism as a career today.

1. Because lately, every time I log into my dusty, old Medium account, this story seems to have come back from the dead. It was written five years ago and for some reason, an influx of people must be Googling, “How to become a gigolo.” What does this tell you about the state of the economy? 😂

2. Because

   Robin Wilding
   recently wrote about the ins and outs of becoming a financial dominatrix and it only reminded me of the best gigolo in the world who also happens to be a long-time friend of mine. Thanks for that, Robin!

So, without further delay…let’s all learn how to make a ridiculously healthy living off other people’s money, shall we?

Stock photo of a random hot guy who may or may not be able to extort money from me under the right circumstances.

Having been a frequent visitor to an island country for fifteen years, I’ve had the privilege (and the disgust) of witnessing the thriving art of gigolo-ism.

For the most part, I’m bewildered that this art even exists, but at the same time, I’m utterly fascinated. So fascinated that I kind of wish I had what it takes to become a gigolette.

So what does it take to be a successful gigolo?

I’ve narrowed it down to a few things: A lack of conscience, pure motivation, and the ability to hop into bed with someone you’re probably not attracted to.

If you possess these traits, you can wake up in a bed of money every day, and set yourself up for life.

The most successful gigolo I’ve ever come across.

I had been dying to write this story for many years. The reason I never did is because I’ve never had a place to write it where I wouldn’t have been found out. If I had written this on my Jamaica blog I would have outed the guy, which was never my intention.

He never expected money from me, so it was not my prerogative to ruin his life when he so generously enhanced mine.

For anonymity’s sake, I’ll name him John. That’s about as generic as I can go.

I met John many years ago when he was nothing but a struggling street artist. Seems artists struggle no matter what country they live in. This one lived in Jamaica and he was a brilliant painter. He was also a taxi driver, which is how we met.

I needed a taxi one day and he came highly recommended to me by an American friend of mine, so I called him up. Long story short, John and I became fast friends and remained very loyal for a long time. To this day, it’s been eighteen years.

Throughout our friendship I watched John build his life up beyond reasonable success. Even better success than I’ve attained as a Canadian.

And he did it all on someone else’s dime.

When we met, he lived in a little board house. His taxi was a wreck, and he was selling his paintings in the tourist craft market. Not much to speak of in the way of money. He just got by somehow.

We kept in touch via Facebook when I was away from the island, and it was Facebook that allowed me to see that he eventually started building a house.

At the time, I didn’t know how he managed to come up with money for a new house but who was I to ask? Maybe he sold a lot of paintings.

After his house was built he allowed me to stay anytime I visited the island for work or pleasure. Before I had my own apartment in Jamaica, I always got to stay at his house for free, which was a major bonus for a lunatic who visited the island three or four times a year.

In John’s house, there were two bedrooms, one of which had an outside entrance, so I could be completely independent. I had a key to my door and could come and go as I pleased.

Once I started staying there, of course, I began posting photos of “my second home” to Facebook. Often, I would tag John in my photos because we were best friends. It was at that point that I learned exactly how he was able to build this house.

On one of the photos I’d posted of myself, and tagged John, I received a scathing comment from some American woman on his friends list. Her comment was something to the effect of, “Yea, you’re sitting all pretty up in the house that MY money built, bitch.”

Anyone who isn’t privy to how common the gigolo lifestyle is in Jamaica may have been taken aback by that comment. But since I’d witnessed the lifestyle up close and personal in many different scenarios, I brushed it off.

It wasn’t my fault that she chose to spend all her money building a house for an island man. Nor was it my fault that I was reaping the benefits, so I ignored the comment and deleted it.

One of my favorite spots to chill…Belmont, Jamaica.

During the years I’d been benefiting from John’s hospitality, he had also opened a business. He built a neighborhood bar from the ground up and it became the most popular watering hole in the community.

So I did what any loyal, foreign friend would do and helped him create a reputation for his bar by promoting it on my blog and bringing foreigners in to spend their money.

This bar was in a community where tourists normally don’t go because they don’t know about it. I changed all that for John and it instantly became an off-the-beaten-path nightlife destination.

Tourists LOVED the gritty neighborhood vibe at the bar and I was the one bringing them in. John made a ton of money from my people and it was my way of giving back to him for being so hospitable to me.

Again, word got out on Facebook, which is how I found out that yet another American woman financed the building of the bar.

John had created his own little empire, all on the dimes of foreign women. At that point it didn’t matter whether the women were in the picture or not, because he’d set himself up so nicely that he didn’t need them.

Here’s the thing…

If John had ever behaved that way toward me or asked me for money, I definitely would have felt a way about what he was doing. But since I was also benefiting from his life choices without having to drop my drawers for him, I mostly just reacted in amazement that foreign women were so willing to give up their life savings for a man who had zero interest in building a life with them.

John was very good at his craft — the best I’d ever seen in Jamaica — and I admit, I was a tad bit envious. 😁

My feet, high atop a mountain in Montego Bay, Jamaica.

One evening, after nearly a decade of knowing him, John and I went out for dinner together and we had a very candid chat.

I asked him why he had never tried to extort me for anything. His answer was very simple. He told me that I’d never given off a vibe that I could be taken advantage of. I’d never acted desperate to be in love with an island man.

Since the first day we met, he felt like I fit in as a local and he knew I couldn’t become a victim.

He then paid the dinner bill. I couldn’t resist asking if it was foreign women’s money paying for dinner. He nearly fell off his chair laughing.

I remember a long time ago, sitting on his veranda one afternoon.

The neighbor saw us and asked, “Is that the new wifey?”

John smiled and replied, “Not this one. She’s family.”

I felt proud NOT to be lumped in with his harem of foreign women who funded his lifestyle.

As twisted as the gigolo lifestyle is, I get it. And I secretly wanted it!

These men are presented with opportunities and they take it. The only reason the opportunity exists is because foreigners present it. If nothing was there for the taking, the taking couldn’t continue.

I’d always told John that I had zero respect for his life choices and he understood why. But it never got in the way of our friendship. We were thick as thieves and always had each other’s backs in times of trouble AND fun.

We enjoyed the mutual respect of friendship.

This doesn’t just happen in the Caribbean, it’s worldwide in many countries. It’s the reason why shows like 90-Day Fiance exist, am I right? 😂😂

I’m dying to know who else has experienced or witnessed this type of lifestyle in their travels.

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