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This Is What Happens When You Source Vacation Recommendations From a Dating App

PHOTO: Boumen Japet/Shutterstock and kavalenkava/Shutterstock

How a Bumble date turned out to be the ultimate return on investment.

Our plan was to do nothing. Absolutely, positively nothing. What we were definitely not doing was making plans. After a brutal six months that involved more airports and transfers and conference calls and deadlines than any of us cared to be reminded of, my two girlfriends and I were dying to just lay by a picture-perfect infinity pool and stare at the clouds overhead. At random—because Mallorca had been fully booked—we chose Malta as our destination. As long as there were cocktails, sunshine, and water, we didn’t care what island we were on.

The “no plan” plan lasted two hours. “We need to do something,” Aarti, an Indian software consultant based in Paris, mewled from her chaise lounge, as the three of us stared up at the white tarp shading us from the Mediterranean sun. “We need Vacation R.O.I.”

No one disagreed. Only a few hours in, our Type-A personalities were starting to show and we had already checked “rest and relaxation” off an emerging to-do list. We needed something else to show “return on investment” for our time on the island. Stories of adventure and romance were not going to tell themselves. So, we sprang into action.

While Aarti and Sylvia, another Paris transplant working in IT, commenced their fierce googling for must-see sights and must-eat restaurants, I, as the only single woman of the group, knew what I had to do: Start swiping. At worst, I figured that if we could find three other tourists, we could charter a private sailboat and go see the clearest waters in Europe that we’d researched so extensively (…in the in-flight magazine on the flight over). The best—if unlikely—scenario was, of course, finding the love of my life.

When I matched with Matt, it felt like I’d hit the jackpot. Matt was hot. Like, really hot. He was a 40-year-old local actor with a fun and fabulous profile. But above all, unlike the other matches who seemed pretty tepid about our meet-up potential, Matt was responsive. Within minutes he called me on the phone. (Who does that anymore?) “I can be your Malta go-to person, if you like,” he said enthusiastically, instantly arming us with restaurant options and Saturday night dance parties by the water.

“Is he meeting us?” asked Sylvia. It didn’t seem so. Despite his eagerness to help, Matt had made some vague excuses about a friend’s birthday, doing laundry, how he had forgotten to pick up his car from the shop and, oh, the fact that he was broke.

“I’m not after you for your money, Matt,” I assured him.

“LOL. You’d be screwed if you were,” he responded.

Despite his eagerness to help, Matt had made some vague excuses about a friend’s birthday, doing laundry, how he had forgotten to pick up his car from the shop and, oh, the fact that he was broke.

He may not have joined us, but Matt checked in early the next day to see if we’d taken his advice. Sheepishly I admitted we hadn’t. We’d found live music and a rack of ribs to die for at The Black Sheep, a pub and cocktail bar in Sliema, the harbor town that housed shops and hotels. After a solid pound of meat, a beach rave had seemed like too much ROI, even for us.

We were up for other adventures, though. “Any thoughts on how we could get on a boat that doesn’t have 30,000 drunk tourists on it?”

Matt told us to look up Captain Morgan, a charter company that ran both cheap boat tours for the masses and lesser-populated catamaran cruises that for eight hours would sail to the most coveted spots around the island.

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His recommendation was spot on. Our first stop on The Spirit of Malta catamaran was picture perfect Crystal Lagoon, a bay on the small island of Comino that, as the name suggests, gave shelter to translucent turquoise waters and the illusion of boats floating on air. We were by no means alone, but with only 40-something people on board the sailboat and a smattering of boats around us, it felt like we’d been one of the few selected for a trip to paradise. Not even the jellyfish that managed to sting me twice could detract from the experience.

“A souvenir from Malta,” smirked the captain, readily handing out paper towels drenched in vinegar.

We next sailed to Blue Lagoon, the area’s most well-known bay where the waters are as blue as advertised, but so saturated with tourists that it looks more like a poor man’s Gray Malin poster than a nature preserve. Not even the crowds could ruin our day, though. We spent hours sunbathing and going in and out of the pristine water, feeling like we had reached return on investment well before the trip’s halfway point.

As the boat turned back towards Sliema, I messaged Matt to let him know we’d loved his recommendation. Matt seemed confused. “Are you going to Sicily?” he asked. My heart sank a little. We hadn’t been communicating for more than a day and not once had either one of us mentioned Sicily. Was he being a tour guide to others as well? Our flirting quickly resumed but in the back of my mind, a reminder to temper expectations was forming. I knew better than to think a man I’d never met had real romance potential, but I enjoyed a fantasy as much as the next person.

“If you’re in Sliema, I’m at a hippy eat and hangout spot,” he messaged. “I look a little rough but I can update you on what to do.”

Sliema Church in MaltaFredP/Shutterstock

At the time, the second part of the message didn’t even phase me. After a day in the sun, who didn’t need a shower? I also knew that by the time we returned to shore it would be too late for the hippy eatery, so I asked him to meet up with us later in Valletta, the capital city and World Heritage site made famous most recently by Game of Thrones.

“Yup! I’m in,” said our mystery tour guide.

As the time came to sightsee, Matt was nowhere to be found. He said he was stuck on a night shoot on the opposite side of the island. With no time to waste, the three of us hopped on a 5 euro tram tour around the capital, familiarizing ourselves with St John’s Cathedral, home to Caravaggio’s “The Beheading of Saint John” and taking photos at the Upper Barrakka Gardens before roaming the narrow limestone streets, chanting “shame” whenever it felt appropriate. (For the record, the Game of Thrones episode “Mother’s Mercy” is not filmed in Malta. Season 1 is. But none of us remembered any pithy dialogue from those episodes.)

When the highly recommended Zero Sei Trattoria couldn’t accommodate us without a reservation, we took their signature carbonara to go (the generous staff at the restaurant trusted us to return their borrowed forks, napkins, and salt and pepper shakers) and sat down on one of the city’s defensive walls to watch the evening’s fireworks.

“I feel like I’ve stood you up,” messaged Matt, as I kept him abreast of our improvised dinner plans.

“You’re like the best boyfriend I never had,” I texted back, still enjoying our back and forth.

“We had some good moments,” he flirted.

Despite never making an appearance in person, the recommendations kept coming. The following day, Matt told us to have dinner at The Chop House  a pricy seaside steakhouse with a stunning view of Valletta. He would meet us after, he promised. As the decadent dinner passed, and we moved on to cocktails at The Palace Hotel rooftop bar, Matt shone only with his absence. He had, however, sent me a link to his short film.

“Do you think we’ll ever meet him in person?” wondered Aarti, who had made it through the first two-and-a-half minutes of the 14-minute epic that I was currently avoiding giving feedback on.

“Does it matter, as long as he keeps telling us what to do?” I laughed, resigned from the idea that we would meet face to face.

“How was dinner?” Matt asked the following morning, sidestepping the fact that he was supposed to meet us right after.

“It was amazing. Not that you haven’t seen it, but the view is stunning,” I told him, sending a shot of the sun setting over the capital.

“I’ve never been, just been recommended,” he admitted.

By now neither the fact that we hadn’t met him in person, nor that he hadn’t actually experienced what he was recommending came as a shock. Ours had all the markers of an average online dating experience–initial enthusiasm followed by ambivalence. (And, frankly, if we were being catfished by our virtual tour guide, at least he was delivering a solid travel itinerary.)

Despite never making an appearance in person, the recommendations kept coming.

But that night, Matt surprised us all by asking me out to dinner—with a caveat: “This is the thing…” he relayed in a cryptic voice message. “I look a bit shabby… Maybe a lack of nutrients… A number of things happened… I’m walking around with my backpack. Please look past the shabbiness and treat me like a guide.”

This was the second message in three days about looking shabby. And the avoidance pattern wasn’t sexy. Had this taken place at home I probably would have deemed this budding relationship not worth the effort, but after a week in Malta, my friends and I were dying to solve the Mystery of Matt. Who was this super-charming actor, roaming the streets of Sliema who had saved us from a week of mindlessness and tourist traps? We had to know.

We decided to meet at Good Thaimes, an affordable and highly recommended Thai restaurant-slash-British pub where the décor is austere but the food is solid.

True to his word, the guy waiting for us looked a bit worse for wear. He was easily recognizable from his profile shots: tall, dark, and—gauntness aside—handsome. He was wearing a black t-shirt, which seemed clean, and he appeared showered. The excessive scruff and undereye circles gave away that all was not well, but he seemed, at the very least, to have a roof over his head.

We made very peppy but awkward small talk for a few minutes, and as soon as we had ordered, Matt abruptly excused himself and walked out the door.

“Where did he go?” Aarti hissed. “Do you think he’s coming back?”

“Maybe? I have no idea what’s happening,” I whispered back.

To his credit, Matt did return (after what we assume was a trip to the ATM) to what must have seemed like an intimidating situation for any man. He knew from the moment we had sat down that he was going to be grilled about his life. “I see how this is. It’s like a job interview,” he laughed.

We soon established that Matt wasn’t wandering the streets. He was going between couches as he was making ends meet by renting out his apartment. That in itself wasn’t a big deal—we all do what we must to get by—but it seemed paradoxical to his obsession with investing in cryptocurrency to de-centralize the power of banks.

He also spoke animatedly of his plans to leave Malta to pursue acting in London. Matt felt encouraged by his new short film and that, on an island with a population of half a million and no real film industry to speak of he was considered a working actor. Eight years ago, he had been a stand-in on Game of Thrones, still convinced nearly a decade later that Emilia Clarke had given him the eye. He’d also worked background on some high-profile productions over the years, which brought him in close proximity to, if not quite in contact with, the A-list.

What quickly became obvious was that there was no romance potential between us. Not because of Matt’s career potential, or lack thereof, but because he was a conspiracy theorist, convinced by social media that traditional news services were out to manipulate us and alien presence was everywhere. By the time Aarti and I found ourselves arguing about female leadership with a man who thought women were more hormonal than men and thus unpredictable, we knew we had dodged a bullet by not meeting sooner. The fact that Matt had remained a mysterious stranger until now had initially seemed unfortunate, but it was really our blessing in disguise. For better or worse, we had waited until the day before we left to discover we had little in common except my desire to explore his island.

While I assumed the outcome of the evening was clear to all, I was surprised to find out that Matt had felt a spark. “We met on a dating site,” he emphatically stated, as if the Bumble “Boom” had been a guarantee of true love, or, at the very least, lust. I wasn’t sure how to explain to him the dismal odds of love at first swipe or that the evening would forever count as a dating disaster. And to what end? There was no point in hurting anyone’s feeling when, as far as I was concerned, we’d all walked away intact—and gotten some excellent travel tips in the process.

“We had a fun night and you gave us lovely advice for our week in Malta,” I finally responded. “I’d say that’s a win-win.” Aarti and I linked arms as we skipped back to our hotel, laughing about our strange little triple date. While we could not have predicted the ending, we definitely had a story to tell. Or, as we’d call it, return on investment.

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