How To Be a Successful Gigolo

Kristi Keller

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Photo by Humphrey Muleba on Unsplash

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

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. I witnessed it A LOT.

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

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 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.

For the purposes of this article I’ll name him John. That’s as generic as I can go with a name.

I met John many years ago, when he was nothing but a struggling 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 was highly recommended to me by an American lady, so I called him. Long story short, John and I became fast friends and remained very loyal friends for a long time.

During the years of 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 I met John, 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 come 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 someone who visited the island three or four times a year.

In John’s house there were two bedrooms, one of which had its own outside door to the veranda, so I could be completely independent. I had a key to my own 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 when I learned exactly how he was able to build his own home.

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 many times, I kind of scoffed at the comment.

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

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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 build up the reputation of his bar by promoting it on my travel blog and bringing foreigners to it.

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 the visitors I brought, 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 yet another American woman financed the building of the bar.

John had created his own little empire, all on the dimes of foreign women. Now 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 for money, I definitely would have felt annoyed 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 was a tad bit envious.

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

I remember a long time ago, sitting on the veranda at the house with him one afternoon, his neighbor was out in the yard next door.

He asked John, “Is that the new wifey?”

John smiled and shook his head, replying, “Not this one. She’s family.”

As twisted as the gigolo lifestyle is, I get it. These men are presented with opportunities and they take it. The only reason the opportunities exist is because foreigners present them. 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 personal friendship, we were thick as thieves. We always had each other's backs in times of trouble AND fun. We respected each other as friends.

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I'm an old school travel writer who's been flung into another writing world through life experience. I have a compassionate eye, a different opinion, and strong words for this world we live in. I also know a thing or two.

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