(Depending on your level of sobriety and how recently you’ve been laid, they might very well succeed.)

Seeing as that I’ve had a weakness for men since toddlerhood, I’ve managed to do my share of dating since moving to the VI in 2009. There’s been some high highs and low lows, to say the least. Sometimes within the same eight-hour period of time. I’m not blaming anyone here, all rides on the bad decision train were taken voluntarily. These experiences have definitely been educational, although admittedly some of the more difficult lessons needed repeating before completely ingratiating themselves within the mysterious folds of my big beautiful brain.

*click for image credit

I’ve noticed several common characteristics among the sort of men I seem to attract. Granted, I’m not getting my ass to church on Sundays to meet a nice Christian boy, but I’m not hanging out in bars every night either. (I drink at home.) And while every one of the men I’ve spent time with in various capacities over the past 4+ years is a unique snowflake, it’s quite easy to lump them into a few distinct categories. These are, by no means, mutually exclusive. To the contrary, several fellows I’ve known fit nicely into more than one.

So without further ado, I present for your educational entertainment, the following listical: (Note: “Bachelor” is used rather loosely in some instances.)

Bachelor #1: The Manchild

Peter Pan Syndrome runs rampant down here, creating a large percentage of men in their thirties, forties, and beyond who have no intention of growing up. Let’s be clear, I’m really far from believing the only proper way to live your adult life is a 9-5 with two kids in the suburbs. My life is quite the opposite of that. But I do think it best to make a nod toward paying your taxes. Having children in the states with whom you are not in contact is a red flag. An adult male should not have to depend on his “employees” for transportation. You get the picture.


  • Can be fun for a frivolous frolic. A carefree burst of adult play time.
  • Allows you to practice your mommy skills.


  • Forces you to practice your mommy skills.
  • If you have anything resembling ambition, their playtime can distract too much from your world of adult priorities.

Most Audacious Fail

Manchild forgets valuables downtown one drunken evening. The next morning, Manchild, Ashley and dog make run to find them. Ashley wears sleeping clothes for quick errand. Manchild so happy to find valuables, he must celebrate.  Manchild might still be drunk from previous night. Cheeseburgers and beers are ordered at 10am. At the next bar, shots are downed at 11:30. Shortly past noon and one bar later, Manchild orders drink for newly homeless buddy and promptly disappears. Manchild leaves phone, vehicle and tab with Ashley. Manchild’s car keys remain with him. Manchild does not return after two hours, during which time Ashley has intimate conversation with wildly charismatic crackhead. Ashley and dog search every Cruz Bay bar for Manchild. No Manchild. Ashley bribes taxi driver with extra $20 so dog can ride home with her. Manchild’s phone receives text during evening hours from woman who reports being happy to see Manchild that day, and btw, his car is downtown, but she didn’t spy his missing shoes. Manchild reaches Ashley’s house around midnight, finds banishment to couch profoundly unfair.manchildmemeblogedit

Bachelor #2: The Not-so-Single Executive

These successful career men have tons of confidence when it comes to courtship. They wear designer clothes, expensive watches, and even treat themselves to mani/pedis on occasion. They take you out to fancy dinners at places you only go on your birthday. Order whatever you want, they say. Get a fancy cocktail, they say. By the way…can I get just one little kiss before I drop you home? Wife/girlfriend in the states? Oh this is just a little fun, they say. We’re actually separated, they say…Good night, I say.


  • Intelligent, stimulating conversation.
  • Large discretionary income.


  • Tendency to have a wife in the states, from whom they might (truthfully or not) claim to be separated.
  • Even if it’s just dinner, you can’t help but feel like a gold-digging mistress.

Most Audacious Fail

After repeated unsuccessful attempts to date Ashley, very-much-in-the-public-eye-and-married CEO asks if Ashley’s mom might be interested. And might he be supplied with her email address? Ashley’s mom, turns out, also prefers not to date married men, especially those who’ve already been rejected by her daughter.

Not so dapper now, are we?

Not so dapper now, are we?


Bachelor #3: The Borderline-Homeless Gigolo

He’s cute. Charming, even. Flirtatious and fun. But you’ll be picking up the tab. He’s in between jobs and places to stay…but glory stories and free time he has in spades.


  • At your beck and call to run errands, lift heavy objects, and fix things.
  • You never have to stay at his place.


  • Always broke.
  • Good chance there’s some moderate to severe substance abuse in the mix.

Most Audacious Fail

Unfortunately-adorable, couch-surfing, Unskilled Gigolo (and manchild) fails repeatedly to earn his keep. Ashley continually left unsatisfied. Unskilled Gigolo’s needs remain met without fail. When Ashley brings fact to attention, Unskilled Gigolo throws arms into victory position, announcing, “I win!”


Regrettably, even the cutest gigolos I’ve known haven’t looked anything like this.


Bachelor #4: The Local

I was warned about this group before moving here. It seems my combination of white skin, dark hair, and blue eyes is an exotic treat for Caribbean men, and these guys are certainly aggressive when it comes to mating rituals. Too aggressive for my taste; it feels like they’re fishing with an extra-wide net, trying to bed anyone with a willing pumpum. I don’t know about you, but this kind of strategy has the opposite effect on mine.


  • Priceless opportunity to learn more about the local culture and customs.
  • My limited experience confirms popular lore where proportion in concerned. Add bubble butts and luscious, velvety skin ala Dove Chocolate commercials, and I’ve discovered that black is quite beautiful, indeed!


  • Cultural differences can be too vast for long-term compatibility
  • Subject to public opinion from strangers. Disapproving sources may give the stink eye. Those less adverse to interracial dating might boisterously declare the obvious, “Me boy wit a white gyal tonight!”

Most Audacious Fail

Traveling Rastaman woos Ashley for several weeks with homegrown hybrid and deep thoughts. Rastaman frequently references his two youths. Rastaman accidentally shows picture of new baby (#3) that Rastaman has neglected to mention. Ashley inquires about Rastaman’s wife. It seems there is one, at present. Rastaman finds no problem courting Ashley on neighboring island. Ashley disagrees. Rastaman respects that.


Regional hero, Bob Marley set the standard for having outside women.

Bachelor #5: The Boldly Age-Inappropriate Older Gent

Next to the local, this might be the type I most frequently attract. I’ve finally contrived a 1970 rule to easily decline their advances without making it personal. “I’m sorry, but I don’t date men born before 1970.” It makes sense. I would like to have a child sometime in the next decade. I would like to be in a long-term, committed partnership when that happens. And as much as I longed to take over his job upon retirement, I’m not interested in being a Mrs. Larry King.


  • Life experience makes them a rich source of conversation.
  • Older men seem to appreciate strong, smart, sassy women more than guys my own age.


  • Probably has kids closer in age to you than he is.
  • Unless he’s aged like Sean Connery or Robert Redford, these thighs ain’t opening.

Most Audacious Fail

Man old enough to be Ashley’s grandfather attacks Ashley’s mouth with his own, mid-conversation. Two different occasions. Two different dirty old men.  Thank.God.For.Listerine. Ashley no longer puts herself in these (non-sober) situations.


A lovely family, regardless. (REALLY wanted his job.)


Bachelor #6: The Serial Monogamist

By far the most benign of the bunch, this guy seems like the greatest catch at first.  And he very well might be the greatest catch. But here’s a little tip…if a guy describes all of his large collection of exes as “crazy”, he probably isn’t practicing much self-awareness and personal reflection.


  • Eager to do couple-y things. Cuddly, affectionate, sweet.
  • Doesn’t play dense (male equivalent of coy) or hard to get.


  • You wonder if he likes the idea of dating you more than he actually likes you.
  • Lots of Exes + Small Islands = Awkward Moments. Also, with this type, you better go ahead and expect a period of overlap on both ends.

Most Audacious Fail

Start passionate romance with girl vacationing on island. Girl lives with serious, long-term boyfriend back home. Continue passionate romance remotely, consequence be damned. Enthusiastically support girl’s impulsive decision to uproot life and move to island. Drop L-word after two weeks of togetherness. When girl cannot reciprocate so soon, build impenetrable wall. When girl visits homeland several months later, start dating next girl. Maybe she will be The One. Not crazy, like ALL the others. Lather, Rinse, Repeat.

So many crazies, so little time.

So many crazies, so little time.

– – –

Let it be said that I have no doubt that a clever man could come up with a complementary list for island women. And I’m sure I would fit into at least one of those categories…in my worst moments.

I can’t be the only one with outrageous tales in this department. Who of my fellow island gyals are dying to dish?

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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