As we near our two year anniversary, having published nearly 200 posts, and seeing a recent influx of new subscribers (if you’re not subscribed yet, you can do so by hitting the polka-dotty “Subscribe Here” button at the end of this post. Press it – you know you want to.), I thought it was about time to paste together a little listicle of some of my favorite posts thus far.

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As this site’s Editor in Chief (don’t you just love the pseudo esteem of self-aggrandizing titles? I do. Clearly.), I know all of our posts like the back of my hand. Better, in fact (I spend little time in actuality gazing at the backs of my hands. Whoa… is that a new mole? ). I’ve come to the point where during pretty much any conversation I’m having on my rock, I can think of at least one of our posts that would correspond perfectly with the topic of the moment and find myself wishing I was able to use my magical powers to freeze the conversation, force the person(s) to read the applicable post, and then resume with new WWLOR fodder added to the equation. But because I do not have magical powers (#sigh), and because I try and keep my obnoxious WWLOR zeal under wraps in public for fear of total social isolation, I do not do this. But wouldn’t that be a cool super power to have? Or would you still choose time travel? Oooh! – or the ability to make kale taste like cake! Ok, ok – irreverent tangent over. Back to this list…

While I pretty much adore every post we publish here (yes, as the Mama Bear of my little Post Cubs, it’s hard for me to be impartial), I forced myself to select 10 that stand out in my memory as my particular favs. Perhaps if you’re new to our site, many of these will be new to you (in that case, enjoy!). Or if you’ve been with us for a bit, perhaps you may have missed a few of these (another good reason to *subscribe*! Hint-y McHint-erson…). Or, if you’re like me and have been with us since the beginning (5 gold stars for you!), perhaps you’ll just relish in laughing along with some of these again for a second round.

So, without further ado, here are my Top 10 Favorite WWLOR Posts Thus Far (in no particular order – *simply click the post title to read it):

– 1 –
Ass Envy

A celebration of Caribbean asses in all their glory.
Who doesn’t move to an island and suddenly long for a bit more curvature in their derrière? There’s a lot to admire/envy around here, that’s for sure. And Ashley’s signature self-deprecating humor is at its funniest in this post. (Note: I also find her descriptions particularly comical because – you should know – she is an amazing/gorgeous woman in real life who has nothing to be self-deprecating about; the light in which she somehow views herself slays me.)

– 2 –
Road-tripping, Tortola-style

Have you ever read an article in some glossy travel magazine about the place you live and thought, “What the hell is this writer talking about? Did he/she even visit here?” Then this one’s for you. Sophie spotted a particularly egregious feature written about her home rock and had to set the record straight. And though I am biased, I think you’ll agree that her version is WAY better – and full of many more LOL moments.

– 3 –
Scavenger Hunting

I think of this post pretty much every week when I have to embark on my grocery shopping trip to town. I try my best to plan my stops, hoping to only have to make two, knowing full well that if the Island Errand Gods are not in my favor, I’ll be making six stops instead – and likely going home with only 3/4 of my list. This post is grocery shopping on an island in a nutshell. And the conundrums Christine G faces are pure, relatable comedy.

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– 4 –
Islands and Tigers and Bears, Oh My!

This one is a classic example of island gullibility (ie. the kind of shit I fall for every damn time). Living on these small town rocks, stories like these spread like wildfire – and stay legendary amongst locals for years to come. Melissa’s playful imagination is the icing on this entertaining cake.

– 5 –
Take a Number

Yes, I included one of my own posts on this list. But before you shame me with my conceit, just know that I’m only doing it because A) this story was THE island incident that planted the first seed of starting this website in my brain (meta!), and B) I had so much fun actually putting it down on paper that I hope you’ll have at least a smidge as much fun reading it.

– 6 –
Dominican Dictionary

Every island has its own lingo – even the English-speaking ones. I wish we had one of these posts for all of our individual rocks, mapping out each island’s unique jargon, but until then, you’ll just have to giggle through this glimpse into life in the DR through Jen L’s observant musings.

– 7 –
Adventures in Island Banking

When Rika first published this post on her own website, I knew we needed it to be a part of WWLOR too. I have said it time and time again – it is the small, mundane things here that will end up driving you the craziest. This is the perfect glimpse into an island taking someone to the brink of insanity via the most banal of tasks – banking. While my heart goes out to Rika through this ordeal, I can’t help but revel in a wee bit o’ schadenfreude at her expense. We’ve all been there, girl.

– 8 –
My New Island Name

There are few stories more prototypically “island” than this one. When Sarah D. first shared this with me, I literally snorted as I read it. I think you will too. It’s a doozie.

– 9 –
Eco Warriors

One of the rock life eccentricities that never fails to make me laugh is how almost nothing is ever executed properly here. Most of the time, you can see the well-meaning intention behind the concept, but something always ends up falling through the cracks and the end product leaves a bit to be desired. This story, of a store “going green” as experienced through Dillinger’s witty perspective, is one of the most humorous examples to date.

– 10 –
Island News: Hot Off the Press!

This was a recent one and I still can’t get over how much I love it. I’m so glad Melissa B. came up with the idea – so much comedy right at our fingertips each day in the “news”paper. How lucky we are!

–   –   –

Which one of our posts has been your favorite so far? Did I miss any?

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Written By:

Current Rock of Residence:

Virgin Gorda, BVI

Island Girl Since:


Originally Hails From:


Chrissann’s home rock in the British Virgin Islands feels bigger to her than it actually is. Though after spending five years on a teensy one acre island, the current 13-mile long rock she’s residing on now IS ginormous, at least by comparison. As with everything in the tropics, it’s all about perspective.

Once upon a time she used to care about things like matching her purse to her pumps but these days, any activities that require a bra and shoes go under careful, is-this-even-worth-it consideration. If island life has taught her anything at all, it’s that few things are more rewarding than time spent in the pool with a cocktail in hand.

As the Editor in Chief of this site, she spends her days working from home with her blue-eyed sidekick, Island Dog Diego, writing, editing, and cultivating content in the hopes of bringing some laughter and lightness to her fellow island souls. She recently published her first children’s book, When You’re a Baby Who Lives on a Rock, and is pretty pumped to share it with all of the island mamas out there. Her days off are typically spent boating, hiking, and meeting up with the neighborhood’s imperious roadside goats, who she shamelessly bribes into friendship. While normalcy was never listed as one of her special skills, Caribbean life may indeed be responsible for new levels of madness. She attributes at least a smidge of her insanity to the amount of time she spends talking to drunk people.

If you’re somehow still reading this and feel inclined to find out more about this “Chrissann” of which we speak, you can also take a gander at her eponymous website or follow her daily escapades on Instagram @womanonarock.

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

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