Dear Love Doctor

Where Can I Find A Long-Term Partner To Settle Down With? – Help Me Love Doctor

Why not send former Kingston-resident Love Doctor your relationship queries? Use the form to submit your question(s).

Love Doctor MontiQuestion:

I’m fed up of being single and stuck on this island with so few prospects of finding a beautiful woman to settle down with and live happily ever after. I’m relatively young and have a decent career in IT, so I’ve thought about moving to North America for work to start a new life.

Friends have suggested that I should consider Cuba and the Eastern Caribbean to restart my life, because the women there are apparently both caring and pleasing on the eye.


Although I like Jamaican women, I find that many are a little on the large size for my personal taste as they only seem to want to dance and eat.

Norman – St Elizabeth

Love Doctor’s Answer

It sounds as though you could be on the verge of a midlife crisis, which often happens to those when they are about to hit a milestone birthday such as 30 or 40. As you describe yourself as “relatively young” then it is a natural concept to explore a move to somewhere else if you feel trapped in Jamaica.

The land of the sweet cool breeze has plenty to offer everyone in terms of love and relationships, but it seems that you would like to discover more than the archetypical Jamaican lady.

Having this latest lockdown, because of the coronavirus crisis, across the island will no doubt have got you thinking about the beautiful ladies on these Caribbean islands.

You surprisingly didn’t mention the neighbouring Cayman Islands, where like Jamaica there are endless nationalities living and working in the capital city. Grand Cayman would probably be a very good bet for your specific IT skills, but the island is pretty small and there really isn’t that much to do apart from work and relax.

The Turks & Caicos islands are another avenue where your IT skills would prove useful yet, like the Caymans, is tiny with not a lot to do. These small islands are extremely expensive places to reside and, with such small populations, as a newcomer you could find romance tricky to unearth.


So your suggestion of the Eastern Caribbean is spot on, although Cuba may not be ideal for you, with North America (Canada and the United States) very competitive for both careers and romance.
Cuba’s technology is not as antiquated as it is perceived, but you would find it extremely frustrating over there with their limited infrastructure for technology. In all honesty it would be like stepping back in time for someone with your abilities and knowledge, plus the government likes to control so much although there are both pros and cons.

If you can speak Spanish then I suggest that you visit Cuba when you get an opportunity. Havana is arguably one of the most interesting cities on this planet. But don’t expect to be able to approach a lady for a date as the government is very strict about relationships with those from overseas. It will be like pulling teeth trying to arrange a date and building up a romance. Yes some of the ladies are stunning to look at, but that applies to every country in reality.

The values of Cuban ladies are generally excellent, and if you could find a woman with the same interests as you over there that would be fantastic. Yet restrictions across the largest Caribbean island mean that you would probably feel more trapped there than you already feel in Jamaica.

So my advice is visit Cuba, virtually ten times the size of Jamaica, where they love music. I recommend Cayo Coco more than the tourist trap of Varadero, to see how you feel about the island and their people. But don’t expect to be able to flirt with the staff, as they could lose their job for showing interest back in you.

The Eastern Caribbean has so many islands, but I would concentrate on just those that could offer you a career path as well as a potential partner.

So I would immediately dismiss the tiny islands of Antigua, Barbados, British Virgin Islands, Dominica, Grenada, French islands (Guadeloupe, Martinique, St. Barthelemy and St. Martin), St. Kitts & Nevis, St. Vincent & the Grenadines and the US Virgin Islands unless you have friends or family there.

This leaves you to concentrate on the high-income economy of Trinidad & Tobago, which boasts the third highest GDP per capita in the Americas behind the United States and Canada, that doesn’t rely on tourism like most Caribbean islands.

The two islands are very different, with Trinidad more business-orientated and with a high crime rate. Tobago is much more laid-back with the local accent and dialects almost hypnotic with their calming sing-song style tones.

The similarities between these islands and Jamaica includes a passion for music and carnivals, food (African and Indian influenced) and patois.


As the Trinidad & Tobago government are extremely protective towards women, it will be rare for you to find any ladies from the islands on such dating apps as Tinder. So forget trying to force an online dating relationship.

Like most ladies across the globe there are certain universal aspects to consider once you get chatting and are genuinely interested in her. To get the ball rolling I would advise you to plan a trip with a friend to see how you find Trinidad & Tobago. But before you do so, explore employment opportunities, as you need to maintain your IT career.

Once you are on vacation then be subtle and build up your confidence by meeting women in the right sort of venues that reflect your personality.

Once you are friendly then you can consider your priorities if you wish to maintain a healthy relationship with a typical Trinidad & Tobago lady. Test the water by always giving her plenty of attention and paying her compliments that you mean.

Only once you feel there is a connection can you tap into her emotions and feelings to create a natural sense of harmony between you.

Be aware that a typical Trinidad & Tobago lady can be demanding compared to European and Jamaican women. She will expect you to constantly buy gifts. Remember that no woman can ever have too many bags or shoes, but you can always drop the budget to purchase accessories, clothing or perfume that will be well received.

These ladies are certainly not after you splashing the cash nor being super rich, it is just that the gesture of giving a gift is part and parcel of their culture that shows you love her.

I have found Trinidad & Tobago ladies to be highly emotional so simply wish to be loved. They tend to thrive off their intuition and gut feelings rather than rely on logic and facts.

Never give a Trinidad & Tobago woman any cause to doubt your love for her, my advice is to ensure that if you get involved with a lady from these islands then take your time to pick the right one for you because you will be immediately required to have your blinkers on.

If you are prepared to be loyal, an inspiration, ready to support and protect a Trinidad & Tobago lady then you have all the right ingredients to make a long lasting relationship work wonders.


Yet don’t be too dismissive of Jamaican ladies, just because you haven’t met the lady of your dreams yet doesn’t mean that she is not on the island. Cupid’s arrows often fire into our hearts when we least expect it, and should you meet someone more local then that would obviously save you the upheaval of a move of over a 1,000 miles.

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