Choosing a Caribbean island as your residence tends to make you more interesting to people who don’t live on a rock. This means I am oft subject to initial intrigue and copious questioning, especially, it seems, from strangers with whom I have little interest in conversing.

It sounds grandiose, but the experience has actually given me far more compassion for famous people who seem tired of the questions most frequently asked of them, and whose answers are sometimes a bit curt. Depending on my mood, I’ve found that my usually warm personality can turn icy in an instant.

OMG, I know just how she feels.

OMG! I can so relate.

When confronted with the rather broad, “So what’s it like living on an island?” my head goes blank in the way I’ve been trying to master during meditation for years now. It’s like when someone asks my happiest memory or favorite movie or song or what books I like to read. Any one answer does not represent the whole truth. And I’m a stickler for the authentic.

My canned response (quite accurate) is, “It’s beautiful and absurd.” This leads to a request for more explanation, and my next canned example, “I’ve never seen more vibrant colors produced by nature. You can drive with an open beer, but will get pulled over for talking on your cell phone.”

Most people ask, “How did you end up there?” A long and, at times, woeful tale. One crumb of information leads to another question, and I can either be evasive, dishonest, or genuine. Unfortunately, my M.O. tends to be radical honesty, so I’m usually truthful, which makes them regret asking, and so the exchange ends squarely in the land of awkward.

…Is this one of those times I should’ve fibbed?

On my last trip home, I received the 3rd degree from a Target cashier. Now clearly, I’m not the world’s most private person, being a writer who writes (perhaps too candidly) about her life. But when the questions are hurled by a stranger from across the checkout counter, you begin to feel a bit invaded. And in this case, a tad scrutinized, if not judged.

“Are you having a party?” she asked in the clipped Minnesota accent that never fails to grip my own speech patterns when in proximity.

“Nope. Just stocking up.”

“Will you be using your Target card today?”


“Would you like one? You get 5% off. You’re buying a lot; it could really save you.”

“No, it’s okay.” I then erred by offering the excuse I must learn to avoid when not feeling chatty because it usually generates more questions. “I live on an island and only get to Target a couple times a year. That’s why I’m stocking up.”

“Wow!” she continued in what I call the Twin Cities Nasal, “You live on an island? Where?”

“In the US Virgin Islands.”

“Do you like it?”

“It’s the longest I’ve lived anywhere in adulthood, so yes, it seems I do.”

“Do you have a husband there with you?”

“Uh, nope…just me.”

“So you’re there all by yourself with no family or friends?”

“Except for the family and friends I’ve acquired there, yup.”

“Are these clothes for your children?”

YIKES!                                                                                                                                         “…I don’t have kids. Uh…I’m not yet 30…” Is it time to stop shopping in the Junior’s section? Did she not hear the bit about having no husband? Is this the family she thinks I acquired?  Two weeks from 30, and I still feel eons from motherhood.

“Oh, you’re buying all these clothes for yourself?” I found her gratuitous shock supremely irritating. Had we not just been over this?

“Yes…well, I only get to the states a couple times a year, so I really go all out.”

“Do you stay with your parents when you’re back?”

Oh for the love. Must we?                                                                                               “Nope. They’re not in Minnesota anymore.”

“Oh!” This further surprised her. “Where are they?”

Christ Almighty.                                                                                                              “Dad’s in Florida. Mom’s in Vegas.”

“So who do you stay with in Minnesota?”

“My best friend.”

“When are you moving back to the states?”

I wanted to say, “NEVER if I have to be surrounded by ninnies like you!” I left the store feeling as if I’d been interrogated by a “Minnesota Nice” version of the Church Lady.


Clearly, Satan is the one keeping me childless and island-bound.

To say that I’m tired of answering questions about living in the Caribbean is an understatement. Funny, since at first I couldn’t wait for someone to inquire about my exotic choice of residence. And still, when aiming to impress, I don’t mind talking about it at all. Because, indeed, it does make me more interesting.

Hypocritical? Yup. Self-Serving? That too.

In some instances, the thought of answering more well-meaning but off-the-mark questions about my life on a constant vacation in paradise is more than I can stomach. This was especially true before leaving my hospitality job, and any energy designated for social grace was exhausted on my guests.

A year ago, I went to the dentist while visiting my mom. He asked why three years had passed since my last dental exam, and I told him I’d been living on a Caribbean island without health insurance. Again, I didn’t intend for my excuse to produce such curiosity. I should’ve known better.

“Oh, wow. You don’t hear that very often.” His surprise quickly turned incredulous, “So what are you doing at the dentist on vacation? What are you doing in Vegas?”

My sigh was surely audible. I’d been asked these same questions by two of his hygienists. And, if I had my druthers, I would not be spending precious vacation time attending health appointments in what is essentially a large desert suburb.

“When you live on an island you end up spending your vacations visiting family, which is what I’m doing in Vegas. I’m going to the dentist because it’s more convenient, and I’m too busy to take care of my basic needs at home.”

“Too busy?! On an island? Isn’t it supposed to be laid back and easy?”

“Yes, but not when you run a small hotel by yourself.”

“That sounds awesome! How did you get such a great gig?”

Since at this point, I wasn’t quite sure how I would force myself through another busy season, and the thought of returning to my work/home catapulted me into the black hole of despair, it was impossible to continue this exchange for another second. We were sitting intimately close: I reclined in the exam chair, he on his little rolling stool. For some reason, the only way I could think to end the conversation was to put my hand on his knee, smile, and say, “Let’s talk about my teeth instead of my job.”

It dawns on me that, if always this brazen, I would likely be much further along in life.

A couple months ago, while dining out for my birthday with some dear friends, I must have been wearing my diva crown because I shut down a line of questioning like it was my damn job. An adjacent couple had used impressive detective skills to decipher that we weren’t tourists. The female half couldn’t help but to inquire as to our glamorous St. John lifestyles. She squeezed herself into the conversation when dessert arrived with a candle and Happy Birthday was sung.

“Do you all live here?” she blurted in our direction, eyes agleam. Last time I’d been interrupted by a curious tourist on a night out, the acquaintance I’d been chatting with disappeared, and I was stuck talking to the woman and her pimply son for upwards of 15 minutes.

Our group responded affirmatively.

“Oh wow! Are you related?”

“Well…no. You could say that we’re island family.”

She opened her mouth to ask more, but I stopped her. “Please don’t make me answer any more questions like this on my birthday. I don’t mean to be rude, but I really don’t feel like talking about it now.”

What do ya know? It worked.

Advance apologies if our paths cross when I’m in this mode. It’s mercifully rare.

I obviously enjoy writing about island life. To the point of passion, really. But I guess it’s different when you get to choose the topic and aren’t forced to answer the same inane questions repeatedly. So, in lieu of the old Hollywood cliche, “Have your people call my people,” from now on, perhaps I’ll just give them my card and direct them to my blog posts.

Written By:

Current Rock of Residence:

St. John, USVI

Island Girl Since:


Originally Hails From:


Ashley lives on St. John in the US Virgin Islands where she can be found drenched in sweat while communing with the hermit crabs who live in her yard. The irony of living in a shac-teau on the most remote part of a tiny secondary island in the Caribbean while spending the majority of her time with a creature named after people who prefer solitude is not lost on her.

Despite constant inquiry as to how long she’ll be on St. John, Ashley has learned in her three decades on this planet that setting one’s life plans in stone is the best way to ensure their futility. For now she remains enchanted with the beautiful absurdity on her rock of residence, which is colorful in far more ways than one.

You can hire her to write and design for you at Bad Ash Babe Creative.

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

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