I flew to Mexico to spend a romantic weekend with a STRANGER after meeting him on a dating site.
- MissTravel is a travel dating website that connects people looking to combine romance with jet-setting
- Men can offer to pay for trips for women, or men and women can agree to split the cost evenly
- Users of the site often meet their dates for the first time in another city or at the airport
- I was set up with a match by the website’s team and flew to Punta Mita, Mexico to enjoy a (long) first date on a luxe resort
First dates can be awkward, but what if they lasted longer than just a cocktail or dinner? What if you had an entire long weekend at an exotic resort planned with a man or woman you’d never met before?
That’s a reality for users of MissTravel, a dating website that offers jet-setters and wanderlusters the opportunity to search for love or companionship while away on vacation.
Users find matches on the site and plan trips together, flying out to a shared destination in another part of the country or world.
Last month, MissTravel offered me the chance to try the site, flying me to a luxe resort in Punta Mita, Mexico for a first date with a stranger.
Romance? I traveled to Mexico to enjoy a weekend away with a man I met on the dating website Miss Travel
Romantic setting: The two of us stayed at a picturesque beach resort (pictured)
When MissTravel first pitched us the trip, there were no immediate takers.
There seemed to be a distinct sugar daddy/sugar baby lilt to the site’s sales pitch — it’s from the same CEO as SeekingArrangement.com — and there are definitely women on there looking to score a free trip, and men offering to pay for it with a certain understanding in mind.
In fact, FEMAIL has even written about women who have used this very site in that way, traveling the world on the dime of various rich guys.
‘This website attracts very successful men who don’t have time to date in the normal way, so this allows them to accelerate the whole thing,’ user Monica Lynn of Alabama explained of why she signed up.
‘They’re going on trips anyway, and they can afford to search through profiles and bring [someone] they like with them.
Even footing: While the site offers an option for men to pay for women’s trips, users can also split the cost. In the case of this trip, MissTravel footed the bill for me and my date
Landed! I met my date at the airport for an early flight to Mexico. Once we arrived at the resort, we were immediately in vacation mode, as we were served guacamole and margaritas
Monica has met men who paid for her trips to nine different countries including the UAE, Italy, and China, while a woman named Alyssa Ramos from Wisconsin has traveled to Ibiza, London, and Las Vegas, with men who’ve footed the bill.
That was, most definitely, not something I felt comfortable with. I wouldn’t want a guy to have any — ahem — expectations, and I’m also not the kind of girl who is partial to posing in bikinis on top of Corvettes for Instagram likes, which I assumed was the M.O. of most of these ladies on MissTravel.
But then I looked more closely. A lot of the site’s users are actually looking for something less transaction and simply want a travel companion — possibly because their friends are busy or can’t afford the trip they have in mind.
After some enthusiastic encouragement from co-workers (who may have been looking forward to a good laugh should the trip have been a disaster), I decided to do it.
MissTravel would fly both me and a guest of my choosing — from a roster of finalists they’d selected from their site — to a high-end Mexican resort to share a very long, and very unusual, first date.
Nearly everyone I mentioned my impending trip to was intrigued, impressed, or excited — except my mother.
Sweet digs: The all-inclusive resort was right on the beach, promising a relaxing vacation
Both of us had our own rooms for the duration of the stay, which was especially fortunate since the showers (left) did not have doors
I was actually surprised by this; I assumed, in her thirst for knowledge about my love life, that she would be thrilled at the opportunity to get both pictures and an entire written report about a date I went on.
But when I told her on the phone, she seemed worried. After giving her all the details — including the fact that we would have separate rooms — she got quiet and then asked, ‘Carly… do you want me to come with you?’
No, thank you, mother, I did not, much as it would have made a great headline to write ‘I flew to Mexico to go on a blind date and my mother tagged along to make sure I didn’t get murdered.’
Luckily, she seemed to be the only one with this view, and even my grandma thought it sounded great — particularly when I told her the guy I picked was a Jewish doctor from Westchester, the gold standard as far as Jewish grandmothers are concerned.
The evening before I left, I stopped at a bakery to pick up some food for the next day. While checking out, the young cashier started chatting, and I told her I was headed to Mexico for a blind date for an article.
I jokingly added, ‘My mom is pretty convinced I’m going to be murdered.’
‘Oh, yeah,’ she replied, nodding her head while putting my muffins in a bag. ‘You’re definitely gonna be murdered.’
There wasn’t much to do except hang at the beach, relax at the pool, and drink strawberry daiquiris; making the getaway less-than-ideal for making memories together
While hanging at the pool, I told another couple that this was a first date — which the couple noted ‘explained the dynamic’
Spoiler alert: I did not get murdered.
Adam (not his real name) and I only briefly texted in the days leading up to our trip, and met for the first time at an NYC airport for a Thursday six a.m. flight — not exactly happy hour.
Luckily, we were not seated next to each other on the way to Mexico, a trip which may have otherwise been filled with uncomfortable conversation and angling for the shared armrest.
When we pulled up to the Casa de Mita resort an hour outside of Puerto Vallarta, though, we had plenty to bond over, as the staff quickly sat us in front of the ocean with margaritas and guacamole. We both dug right in, which was a good sign, because you can’t trust a man who doesn’t like guacamole.
Ready to get into swimsuits, we went to our separate rooms. They were beautiful, but I was especially glad we weren’t sharing when I spotted the shower — which had no door and opened right into the room.
I know some girls might be happy to put on a bath time burlesque on a first date, but I guess I’m just old-fashioned.
Speed dating: We ate every meal together at a table with a view of the water, which felt a bit like eight dates in very quick succession
Because most of the weekend involved laying around, most of the interaction was over meals
The first day was generally uneventful. After laying out by the pool for a bit, we each went to our rooms for a ‘quick’ nap, only to discover at nine the next morning that we’d both slept through the night.
So my second-ever meal with Adam — call it a second date, if you will — was over breakfast Friday morning.
Despite some worrying that we might not find anything to talk about and it would be a long, awkward weekend, the two of us actually had plenty to discuss: our favorite restaurants, our jobs, and — I wasted no time — the reason why a nice guy like him signed up for MissTravel in the first place.
Adam, who was a few years older than me at 35 (I’m 29), said most of his friends were married with kids — leaving him few travel partners. He signed up hoping to find people to hang with on foreign getaways, and had no interest in being anyone’s sugar daddy. Phew.
Over the next two days, we spent some time on the beach, laid out by the pool to read, and ate all of our meals together.
Unfortunately, there didn’t seem to be a romantic spark — though I wondered if a different setting would have changed that. The resort, while beautiful and romantic, was tiny and intimate. That’s great for longterm couples, but maybe not so much for a guy and girl just getting to know each other.
The spot was definitely romantic, which was perhaps more befitting of a longterm couple
Real world: While my friends were all excited about the trip, my mother was very worried about my safety
Had there been nightlife, dancing, shots, illicit party drugs (just kidding), or even some sort of sight-seeing, maybe the weekend would have progressed a bit differently. Or maybe not. Dating is dumb.
As it was, we really just hung out together all day — together, but not together-together. At one point on Saturday, Adam went up to his room to nap, and I struck up a conversation with another couple in the pool.
When they told me they’d been visiting there for years, I explained the story I was working on and revealed that Adam and I had just met that weekend.
‘Ah,’ the man said. ‘That explains the dynamic.’
‘Ah,’ I thought to myself, silently. ‘The people here have been judging us all weekend.’
That night, Adam and I had our last dinner together, watching the sunset over the beach. Around ten, we finished up and headed to our rooms for the night.
The next day, we traveled back together to New York, by way of a layover in in Minnesota. In between flights, my mother — the same lady who wanted to chaperone so I wasn’t brutally dismembered by this internet stranger — texted me, and seemed disappointed that I didn’t find true love with him. Moms. Go figure.
Though I didn’t find love, I did find that traveling with someone I’d just met was an adventure
Finally, we began boarding again, when the flight attendants announced that they’d be checking our carry-on bags.
Realizing I didn’t have an exciting finale for this story — we didn’t elope, and he also didn’t try to smuggle back drugs in my suitcase, Bridget-Jones-style — I briefly considered screaming that the airline could pry my carry-on out of my cold, dead fingers and having Adam record it on his phone. How’s that for a finale?
Adam seemed amused, but also a little scared by my suggestion, and ultimately we boarded peacefully without our carry-ons, flying into JFK before hugging each other goodbye.
In the end, there was no romance — not even a kiss — but it was still a fun way to spend a weekend.
Meeting up with a stranger on vacation seems like it could actually be a great idea, on two conditions: One, if you go somewhere where there is plenty to do to keep you busy. And two, if you’re prepared to go solo should this stranger be a weirdo.
I can’t vouch for the weirdo-to-normal-person ratio on MissTravel, but I did manage to find one totally normal, nice guy on the site — which seems like a pretty good sign to me.