What Happens When You Go on a 48-Hour Blind Travel Date in... Puerto Rico?!

I think we all can agree on one thing: Dating is rough, and blind dates are even worse. And dating in New York City? That might just win the nightmare. 

Ok, so that was three things. It feels like we’ve run the 'dating method' well dry attempting to find a true match, amirite? 

Well, we have. That is, until now. So then, what the ever-living f*ck is Travel-Dating? 

I have this theory.

Everyone considering marriage should go on a road trip, preferably in a foreign country, with their significant other, before tying the knot.

I'm no relationship guru, but I stand by that theory. 

With that theory in mind, this method of dating should, potentially, in some backwards warped way, work… right?

So then, what happens when you do that as the jumping off point in the relationship, instead of as the ultimate final test before jumping off into the sunset, together, forever?



via Lauren Breedlove

Let’s rewind for a hot sec. Your eyes have not deceived you. I was, in fact, in Puerto Rico on a blind date for 48-ish hours with an outright alien–to me, anyways. A travel-dating website named none other than MissTravel.com was the source, of course. 

I had been approached by the site and asked if I’d like to experience a “travel date,” sharing my account of the venture. Totally normal. Except it wasn’t- I didn’t know such a site existed, never mind the actual concept being a real thing. But in an age where all things in life occur online, including farmers having their own website for love hunting, I shan’t have been surprised. 

"Travel and dating? Let’s make it a thing!" is how I imagined the conversation with the creators went.

Let's be real, there's always room for one more. Out of the loop or not, if I agreed to this, I was about to pioneer a new trend in the dating world. Yikes. 


A touch of skepticism, a vat of curious-ness, and a dash of concern for my safety; there was an interesting cocktail I'd muddled in my thoughts and shaken relentlessly in my mind, a stiff drink, I'm sure. 

I pictured myself in a long gown–preferably with sequins–on reality TV, a mini-bachelorette show of sorts, if you will. We were headed somewhere beachy, and although I was pretty sure MissTravel wasn't going to arrange an over-the-top date involving helicopters transporting us to a private concert, it was close enough. 

I asked all the vital questions, mainly about sleeping arrangements. My fantasy suite fears were put to rest when I was assured we'd have individual rooms. Phew.

Welp, there was only one more crucial thing to find out: do I bring my own roses? Or would they supply them?



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We're married now and have 2.5 buns in the oven. Strange, I know.

Just kidding.

A lot can happen in 48 hours. But, not that—for me, anyways. I knew exactly three things as I landed in Puerto Rico:

1. I had just traveled 1721 miles for a date. A blind date to boot.

2. It was humid AF.

3. This might just be one of the most ridiculous things I had ever done.



via Lauren Breedlove

Thing is, I don't enjoy dating. Fact. It's a STRONG dislike in my book. People are weird. Dating is awkward. Oh, and people are weird. So, naturally, I said yes. But I can't turn down an adventure

I launched into full on investigation mode via the MissTravel site, which launched in 2012. I uncovered a few things. The main one being that it works pretty much just as you’d expect a dating website to operate. There’s potential mate profiles in abundance per usual, and you can choose to go on a travel date with someone that will:

A) pay your way

B) split it 50/50

C) like for you to pay their way

Disclaimer: In real life, I would only ever agree to option B. But, because this wasn't real life, the only thing I had to choose was my travel companion. That's how I found myself selecting a suitor from an e-mail peppered with personality/background blurbs and a smattering of photos. 

I had requested Ryan Reynolds, but since apparently that wasn't possible, I chose from a pool of seemingly cool guys from all over the States. They had agreed to go on a travel date that would be written about, specifically with and by yours truly.

Sure, I had the classic fears of being paired with a serial killer or even worse, a guy who's childhood stuffed animals reside in the back window of his car.  

In the end, I picked my travel-date because in one photo he was holding a beer, and in another he was holding a giant turkey leg. It seemed we'd get along just fine.



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Six days before take-off, TD (that's what we'll call my travel date) and I were put in touch. We chatted via text about the impending travel date. There were a lot of exclamation points used. He was excited, I was…nervous.

The conversation seemed to flow, and we uncovered a mutual fondness of dive bars and lists. He seemed up for anything, gaining a few points in my book. Also, he worked with beer, so more points.

We joked about fake travel-date guidelines that may or may not help the situation, and decided to create some of our own. Some serious, most ridiculous.  They ran a wide spectrum from freedom in asking any questions to trying Mofongo (a local specialty), and high-fiving in a cave. I started to think that maybe this would be, dare I say, fun?

He was aware that I was writing about this experience and because of this, I wondered if I would be getting the real TD or a show version of him. I figured I would get more of a sense when we met.

I did question the expectations part of travel-dating. 

There were payment options, destination options, and companion options…but what about pre-set expectations? I guess that's something both parties would just have to discuss before agreeing to jet-set with them. Like all things dating, what works for some, might not work for others.

I wasn't sure what his thoughts were, but I was going in with zero expectations. I was doing this for the random experience of it, travel, and as someone who despises dating, to push the envelope. I was fairly positive this wasn't going to lead me to true love. 

Anyone that learned of my venture was literally dumbfounded, as though this travel-dating thing was some newfangled crazy idea impossible to fully understand. And they were right.



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I was greeted in San Juan by a text from TD saying he had missed his flight. So, despite the original plan to meet at the airport and share a cab to the hotel, I was gifted a few more hours, delaying the inevitable awkward meeting. 

Suspense. Building. 

I checked into the cozy B&B where our home base would be for the two-night travel-date. The Dreamcatcher was a ridiculously cute vegetarian haven with a hammock lounge, ample opportunities to do yoga and meditate, and a mere block from the beach in the Ocean Park neighborhood of San Juan. 

Upon check in, the receptionist asked the perfunctory question, “So, what brings you to San Juan?”

“Well…” I lead, explaining the travel-date situation.

She literally. Couldn't. Even.

With every sentence she became more rapt, the whole idea exciting her to no end, causing her to spew things like,

“Oh my gosh that's so exciting, you're going to have to send me the article!”

She might be our #1 fan.

“I've never heard of that before!”

Me either.

“He's staying in the ROOM right across from YOU!”

Oh, good lord.

“I might come knock on your door tomorrow to find out how it's going!”

Please don't.

I wanted to tell her, “Oh just tune into our reality television show,” because that's exactly what it felt like, but I didn't want to give her a heart attack.

She toured me around the property, charm exuding from every nook and cranny. It was clear as to why this was a destination for yoga and meditation. Besides tipping the peaceful scale, there was a lot of incense burning, so it was obviously legit. 

I even considered for a moment that maybe I should meditate to calm my nerves. Eh, nope.

The last stop was my room; an adorable, spacious retreat with a balcony fit for a queen, including an outdoor shower, and evidently my very own tropical bird. Or at the very least, the constant call of a tropical bird.

I got my bearings a bit and located a little bar on the beach right by the Dreamcatcher so we could have a direct destination in mind when TD arrived. We were behind schedule, and I was remarkably thirsty. 

There was a cocktail of feelings going on, mostly involving nerves and a lot of them involving being sweaty. I was also in dire need of a cocktail, ironically enough.

In the five minutes it took for me to check out the beach, my hair tripled in size. Damn humidity. If there was a camera guy, he undoubtedly would have been laughing his ass off.

At this point, it was almost time to meet and I had to pee, badly. This is where the only downfall to the B&B came into play. Unfortunately, the shared bathroom was in the direct path to TD's room at which he was due to arrive any moment. Great.

I could just picture the pure joy on the receptionist's face in witnessing this ever so climactic meet-cute IN FRONT OF THE BATHROOM. How romantic. 

As much as I didn't want to take that way from her, I did not want that to happen.

Alas, I potty-danced around my room to the beat of the nonstop squawks of the resident tropical bird, when I received a text from TD. He had arrived, and it was time to actually do this thing.



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We met like any other strangers would meet for the first time at a B&B in Puerto Rico on a travel-date: with a knock on the door, and an awkward hug. 

We quickly agreed that a drink was in order, and I knew juuuust the place. The tropical bird cawed in approval.

After finally using the bathroom, we headed to the small beach bar I had scouted previously, and I was thrilled to be somewhere with alcohol. Our beers and bodies sweated simultaneously, chatting in the overbearing company of the humidity who had quickly become an obnoxious third wheel. 

I drained my beer in record time. My fear about getting the “real” TD was quickly put to rest as I could tell he was as genuine as they come.

We discussed our backgrounds and other first date jives while my main question burned a hole in my pocket. I waited until we moved locations to a local tapas joint and ordered some tapas—shocker. I wanted was dying to know how he ended up on MissTravel

I tossed that burning little nugget out there and was slightly (okay, a lot) disappointed to find out that he had only been signed up on the site for about a week when he was contacted for this travel-date.

Ironically enough (though not as serendipitous as one would hope), he had read an article about the site, created a profile, and then ended up being part of an article about the site. Well done bringing it full circle, well done.

I both appreciated and didn't like that he was a newbie. He wasn't a travel-dating pro, so I took comfort in that we'd trail blaze this together. But I wanted to know more about people who made a habit of travel-dating, and their expectations surrounding the dates. 

I suppose it's like any other dating site though; people's expectations and motivations are always going to differ. Only difference is, on a travel-date, you're stuck with them for longer than just a drink.

We wrapped up the evening by planning the following day, a day requiring a car rental, exploration, checking off some of our curated guidelines, and inevitable awkward silences (of course). I was glad that TD seemed up for anything on account that I abhor organized tours and much prefer to star in my own 'choose your own adventure' book.

We retired to bed in our respective rooms after ending our night much like it began: an ungraceful doorway dance involving what I thought was going to be a fist pump, but turned out to be a hug. Try as I might to sleep, the less than sweet sounds of an incessant tropical bird wouldn't allow it. 

We had a big day ahead.



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The next day we hit the open road, smoothies in hand, in what can only be described as a low budget car obtained from a true gem of a lady named Venus who does her job in a box-sized trailer in the middle of a San Juan parking lot. The day was off to a glorious start.

We grabbed an idyllic spot under two palm trees at a stupidly beautiful beach named after the banana; Chiquita something or another. Under any circumstances at all this was a disgustingly romantic spot. Us, the perfect palms, the 50 shades of blue water, and about 63 of our closest Puerto Rican friends.

Romance was alive.

Except it wasn't... yet. I take a while to get comfortable with someone, anyone. I move slow. I'm a snail-dater (I made that up, but just go with it). I may not have been feeling any mushy feelings yet, but I was still willing to give it a go.

Next up in our coastal exploration was a cave, but not before arguing the finer points as to how one defines spelunking, as I was convinced we were about to indeed, go spelunking. I defined it as “cave exploration,” and TD was adamant about it involving “underwater diving through caves.” 

Our first argument, how cute. For the record, I was right.

The dictionary definition:

spe·lunk·ing: the exploration of caves, especially as a hobby.

So, we spelunked. Dodged some bats. Climbed on some rocks. High-fived in a cave. It was pretty amazing. How could you not have a good time with someone when doing things like this?!

We took our time in the car to learn things of importance about each other. Things like….

I don't like clowns.”


I can't pass a Taco Bell without ordering a crunchy gordita.”

The further we drove along the coast, the more aware I was of uncomfortable silences; repeated periods of silence that, in a relationship, become “comfortable,” but, because, well, you can't attain that level of comfort with someone in that amount of time, never were.


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Just like that it was mid-afternoon. I realized the smoothie was a gazillion hours ago, I was starving, and in clear danger of morphing into the hangry version of myself. 

Again, this was something that normally wouldn't happen until at least a few weeks or so into dating. BUT I WAS FAMISHED AND NEEDED ALL THE FOOD.

Trying to keep my hangry tendencies in check, we immediately pulled into a restaurant that boasted over 100 combos of Mofongo. If that didn't sell it for me, the audible growling of my stomach did.

We ordered enough Mofongo to feed a family of six. 

We had Mofongo for days. 

Mofongo turned out to be mighty tasty. 

I tried to say Mofongo as many times in lunch conversation as possible for my own amusement. 

I was high on Mofongo.



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That night was our second and last night of the travel-date.

We stopped into reception to have a cab called by my favorite receptionist/founder of our fan club. Seeing us approach together, she looked like she'd just won the goddamn lottery, but only seemed to ask me how it was going with her eyes.

"It's going… fine," I said, not actually saying anything at all. 

"Please call us a cab," I blurted.

We embarked on a bit of a bar crawl involving a dive, rooftop, and a trendy speakeasy, a perfect trifecta.

Bar #1:

Do you take shots?

If I do, I only have one for the night.

"We'll save that for later then.

Oh we will, will we?

Bar #2:

With each empty glass we delved deeper into musings about past relationships.

Bar #3:

We discussd the logistics of travel-dating and how it may be hard to judge the relationship progression in this type of situation given the short period of time. 

A point is made about potential pressure to make a move before the date is over, seeing as both parties most likely don't live in close proximity—but without forcing anything before it would happen naturally.

Solid point, and a tough call.

The hypothetical situation speak was making me all kinds of nervous. Not that any of it was related to us, per se, but if it was, I wasn't prepared to deal with a move being made.

I don't kiss on the first date,” I word vomited random dating trivia about myself in hopes it would be an effective shield.

Was this still considered the first date? Or was that last night? Mere technicalities. Although I was having a fun time, I didn't feel that spark. Also, me = snail-dater. Remember? 

I attempted to steer the focus away from us and talk instead about awkward dating stories, obviously.

I yelled in my date's face once in a moment of panic with a weird accent I had never used before.


A girl peed in my bed one night.


It may not have been the best tactic, but it did the job.



via Lauren Breedlove

The Dreamcatcher provided us each with darling hot pink 'HOLA' postcards to send free of charge to anyone in the U.S. at the end of our stay. It was such a cute idea I could barely stand it. 

TD thoughtfully suggested we write them to each other, and send them off without looking.

So we penned our inner most thoughts, or, if you're me, neutral ones sprinkled with inside jokes, and handed them over at check out. 

Joking aside, I actually loved the idea and was pissed I hadn't thought of it myself.

The curiosity of what lay on the backside of that postcard was going to drive me nuts. And I'd have to wait until it arrived via old school snail mail. I mean, who doesn't love getting mail? It was a superb way to end the travel-date. 



via Lauren Breedlove

Travel-dating: It's a risk, but why it could work?

I see how travel-dating heightens emotions, and, much like The Bachelor, create ideal conditions for schmaltzy feelings to bud. I mean, you're (most likely) visiting a postcard-worthy place, and you're venturing around with your chosen partner. Sounds pretty dreamy.

It seems like the ideal way to meet someone, as your "vacation self." 

When we're on vacation we feel free, relaxed, and allow ourselves to eat ice-cream sometimes twice a day, so of course we're happier. It encourages us to be more of our true selves. But, will that survive in the real world?

Does travel-dating get down to the nitty-gritty part of a relationship? Does it cut right to the part that everyone needs to know before getting in seriously deep? There are pros and cons, naturally. 

Travel-dating hits the point surrounding my theory about traveling with your significant other. It provides the ultimate opportunity to learn a lot about that person, and truly test your relationship.

There is however, something to be said about the natural progression of a relationship. Travel-dating forces you to deal with situations that probably wouldn't normally come up on a first date—or even pretty early on in a relationship (like my hangry-ness), that is unless you make a habit of taking road trips as a first date.

Bottom line: travel-dating is like any other kind of dating: a risk, an endeavor, and more often than not, a sh*t show. You have to figure out what works for you, and if jetting to a locale with a complete stranger is it, then go for it. Weirder things have happened…and probably on a date in your hometown.

Maybe for people like myself that love travel, but don't enjoy dating, it's actually a decent option. It's extreme enough that it almost forces no expectations.

While I didn't catch any feelings of the lovey-dovey nature, I laughed, met someone interesting, made a new friend (and pen-pal), and ate half my weight in Mofongo. I couldn't have asked for anything more. TD was a total gentleman, for which I am grateful.


He offered his hand when we stepped down sketchy stairs on the beach, and opened any door he could find for me. Chivalry is not dead, people. Turns out I have a hard time accepting it though. Huh. I might have actually learned something from this experience.

We all want someone that will look at us like we're made of rainbows and vice versa. Can that happen on a travel date? Who knows. It's a mystery as to when sparks will fly. We just have to take the chance, put ourselves out there in the world, and if, at the very least you end up with a postcard buddy...well, that's not so bad.

My only regret? 

I never did see that damn bird.

[Feature Image Courtesy Lauren Breedlove] 

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