They are single, they are fabulous, they are island girls, and they are over 40.

The Caribbean is a fantastic place to live – I have said it again and again. But I’d recently got to wondering if the same was true for those who are here and not a part of a couple like me. What’s it like to be single and over 40 in paradise? I gathered some of my unattached friends and asked them this very question over a bottle (or two…) of wine. Here’s what I discovered in my research:


single Caribbean island girls with rose

Forty seems to be the new twenty.

I definitely see some truth to this statement when I look around the table at each one of my single island gyals. All of them are successful, independent, and yes, fabulous. Some with kids, others without. Some are divorced, while others have not yet found Mr. Good-Enough-to-Settle-Down-With. That’s the thing – when you get to a certain age, you stop believing this bull crap Disney has been feeding us for so long: that we all must wait for our knight in shining armor aka Prince Charming to show up on his white horse and rescue us form our “depressing” singledom.

By now, most of us have discovered that the castle actually belongs to his mother (the evil queen) and happily ever after usually means the prince is the one who’s happy as long as you do what he wants, which can mean being someone you’re not. So many of us have been there, eager to please complete with a smile on our faces, until one day we wake up and realize that we have lost ourselves somewhere along the way.


There is nothing depressing about being single and over 40 – but does Caribbean society agree?

The advantages of being single and over 40 are clear, no matter where you live. You do what you want, when you want, and with whom you want. Oh, that incredible feeling of complete independence.

The single island woman is nothing new to the Caribbean. There are enough single mothers out there to prove it, but what is still unacceptable to most Caribbean people is a single woman who knows what she wants and doesn’t rely on a man to get it. “What’s wrong with you?” is still a question repeatedly asked to single island women. To assume that just because a woman is single, has a career, and the looks on top of it, that there must be something wrong with her is atrocious. But perhaps the “something wrong” lies less in her and more in the lack of options out there on the island…


island dating in the Caribbean

Limitations are a part of the reality.

The Caribbean has a tiny pool of nice, good looking, intelligent, and fun fish. Most of the nice guys you meet have, at one point, been with one of your friends or were even married to one of your girls. Or that great guy you’ve been waiting for to finally become single turns out to be gay. Then you have the Tourist Guy, who’s only out for some island fun and then he’s done. Mr. “I’m Afraid of Commitment” and Mr. Married come in all shapes, sizes, and colors. One thing we know: e-Harmony will never be able to set up shop here.

Island life is also quite limited in activities for dating. There are only so many places you could run into a nice guy: church, a bar, a friend’s party, the office, or the beach – and each of these locations presents their own set of challenges. The office, for instance, never ends up being a good idea.


Are single island women over 40 lonely? They must be.

Or so the common assumption goes. Although the single girl will at times miss the company of a gentleman (or gentlegirl), they are not at all lonely. Once you are happy with yourself, you will be happy with your own company and very content with your life the way it is. The biggest misconception is that being alone is the same as being lonely. Caribbean parents especially seem to have a problem understanding the difference. And if you do happen to feel lonely at times, it is easy to call up some friends and arrange a fun get together.


But what about SEX, baby?

Let’s be honest, you are now at an age that you know what you want or, more importantly, what you DON’T want. In your early 20s and 30s, you were less picky, less selective, and were still looking for that Happily Ever After. Now, in your 40s, you no longer have the patience to teach anyone the basics of sex or how to please a woman. To all of you Caribbean men now thinking, “Oh, she’s just been single too long.” – you, sir, are the problem.


Caribbean island romance beach sunset


Some women are interested in a committed relationship while others just prefer a friend with benefits or one night stands. The single island girl over 40 is also no longer interested in changing her ways to adapt to your life. In fact, you’d better be ready to accept her the way she is because she really is quite comfortable with the life she has created for herself. Don’t think for a minute that she will change her ways merely to please you.


How young is too young?

Obviously 19 is cradle-robbing, but anywhere over 30 seems to be acceptable for this bunch. Too young means they tend to get clingy. At this age, most women have already raised children and are not interested in raising a boyfriend as well. Let’s also not forget that the younger they are, the less they tend to “last” between the sheets. This does not mean that the over 40 man does not have this problem though too. Some older Caribbean men are also set in their ways and are more interested in pleasing themselves and to hell with what the woman wants. The over 40 island girl has no time for this.


Advice to the single 20 and 30 year old island girl:

Enjoy your life as much as you can. Build your cake yourself and the cherry will be the person you settle down with. If the cherry decides to bail somewhere along the way, it doesn’t affect the structure or the taste of the cake at all. Now who says you can’t have your cake and eat it too?


To quote one of the single island gyals:

“40 is like being 20 – with 20 years of experience. So if you’re reading this and you are 40 or over, congratulations! If you’re not, hold on, the best is yet to come!”


Caribbean island girl toast pool day


–   –   –

Are you single and over 40 on a rock? Does the above ring true for you or has your experience been a different one?

Current Rock of Residence:

St. Maarten

Island Girl Since:


Originally Hails From:


Riselle is a happy-go-lucky island girl from Curaçao living the island life on the beautiful yet tiny island of St. Maarten/St. Martin. She has a passion for travel and adventure and not long ago decided to follow her heart wherever it may lead her.

Her days are now spent being a pet-mom to her 6 dogs and 3 cats and a wife to her husband of 4 years, James. Until recently, she was a full time planner and designer at her own event planning company but a sudden revelation in February of 2015 made her put her business on hold and change career paths. New career: unknown. In an attempt to find herself, she decided to take up blogging, which to her is one of the few occupations where you don’t need to wear much, flip flops are always in season, and tattoos are not frowned upon.

Impulsive, a true people person, happy, friendly, always willing to help, and determined are just some of the words that describe her best. Of course she can also be headstrong, bossy, spoiled, slow to forgive, short-tempered, irrational, and at times grumpy, but this can easily be fixed with coffee or wine. Preferably wine.

Travel is her one true passion besides her love of animals. Any time she is not able to travel far, she is content with exploring her little piece of paradise.

You can read more about her travels, island life, and adventures on her website, The Traveling Island Girl.

Want to read more posts by this writer? Click here.

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