Puerto Rico has never been good to my husband and me. Never. Our first trip to PR together was our first trip together as a couple. Even though we’ve known each other forever, this was completely foreign territory – truly alone together for an extended period of time. The pressure was thick.

I don’t think I’ve mentioned what a overthinker I am. This serves me well as a person who puts on events, and served me well in my previous life as a P.I. (a job I had for all of 3 years but refer to like it was my life’s work because yeah, it was that cool), but in every other aspect of my world it’s a major hinderance, to say the very least. I can spend days trying to choose a water bottle or laundry detergent. I come by this honestly, it’s a family trait that annoys the shit out of me when I see it in my relatives, but I understand.

So, for our first trip to the Isle of Enchantment I spent weeks looking for just the right romantic hotel. I scoured websites (I feel like Travelocity and Expedia were the only options then), I asked friends, I made calls. We happen to have a friend in PR who owns nightclubs, my first trip to PR with girlfriends was straight FIRE, mostly due to his assistance. So of course I checked with him for a recommendation, and of course, because I was in New York and knew nothing about this island completely disregarded his rec (and discount) and being too much of a party atmosphere for this all important romantic getaway. I found a lovely place, right on the beach, small and intimate.

I should’ve known when the taxi driver asked if we were sure of the address that this was going to be a problem. Second clue? The “beach” was clearly the main Tent City for the island. You would think the final straw was the huge steel gate at the entrance, but we persevered. No, the final straw was of course the room. A room only a crackhead could love.

In the days when wireless may not have even been a thing, but thankfully cell phones were, I started calling all over the Island for something else. F pretty much just stood by the door, suitcase in hand, scowl on face, waiting. My generous friend who’d offered me the great party hotel at a great rate was no longer quite so generous. Things were looking bleak until I finally found a Marriott with a room. Praise Jesus.

Since we’d been in the room less than 15 minutes (it seemed a lifetime) and the room was probably more accustomed to renting by the hour we didn’t have to pay and broke out to the Promised Land of chain hotels. One problem: when I booked I gave my debit card, and because it was The Most Fucked Up Trip Ever the hotel accidentally charged me for the full weekend. Twice. So now I’m broke, and my boyfriend, a freelance writer at the time, was cheap. Good Times! Oh, I forgot to mention two weeks before I’d torn my meniscus so I had a brace and a cane, and a day before my boyfriend threw out his back. So now we’re annoyed, broke and gimpy. What more could you ask for!

Well you could be asked to be seated next to an old woman with a screeching parrot on the flight home when birds are your biggest phobia. There, NOW it’s the best trip ever!

Take two: The redemption trip. We were both making more money and decided to stay at an all-inclusive resort on the Caribbean side of the island. But first, we’d spend one night in San Juan to visit the romantic Bioluminescent Bay because yeah, we were going to have a romantic PR trip if it killed us. It almost did.

To be honest it’s a miracle we survived as a couple much less later got married after that experience.  You go with a group in the dead of night to a bay by kayak, single file, so you can navigate the mangroves on the way to the awesomeness. Now, there’s not a whole lot that freaks me out, but one big thing is water in which I cannot see the bottom. Another is things touching me that I can’t see. Why did I go on that boat? I know two couples who broke up after trips to Puerto Rico. I completely understand.

I was the lead in the kayak, and each boat was given a whistle in case you were separated and needed a rescue (I should’ve turned around right then). I’m proud to say, we lasted a good 15 minutes before I blew the shit out of that whistle.

My boyfriend, whom I loved, who at this point I’d probably started to think this may actually be it. My brilliant writing, curating boyfriend. Couldn’t (or wouldn’t) paddle worth a shit. At one point, after landing in the mangroves for about the 5th time I looked back at him as I struggled to turn us out, and this…man didn’t even actually have the oar in the water. Done. Fortunately what you see when you get there was worth almost wrapping a root around his neck in the pitch blackness, knowing no one would ever know.

You would think third time would be the charm, but the night before we were leaving, my dear, beloved grandmother, who I and everyone who knew her loved more than cooked food died at 96.

Why am I writing this post? Because I saw a post on Facebook for this place. Could this be the moment when husband redeems himself from the selfishness and pain that almost led to his demise by my hands? Can we now, being an official team for almost 11 years go forth and conquer the kayak? Should we do it? Should we??

That could possibly be the dumbest thing I’ve ever considered.

The second dumbest thing? Considering it as the location for our extended family summer vacation this year. But it wasn’t until I started writing this that I realized what a foolywang idea that is. So I think, as far as Puerto Rico is concerned, I’ll side with Anita and let it sink back in the ocean.

However, there is one thing that never disappoints. One word: Mofongo. Adios!