Despite editing a website that constantly promotes the power of solo travel, particularly for women, I hadn’t actually traveled anywhere solo. I’d been to the odd work conference alone and been on group press trips where I didn’t know anyone, but backpacking through Southeast Asia as a fearless solo traveler — something nearly all of my coworkers have done at some point in their lives — has never appealed to me.
I crave companionship. My best travel memories are all moments of connection between me and my travel buddy, which has almost always been my mother, my sisters, or back in the day, my ex-boyfriend. I simply cannot fathom enjoying traveling alone. It’s not just a preference for me — it’s a deep-seated fear rooted in lifelong anxiety disorder and clinical depression. I can’t enjoy a day at the park because I’m left wondering how much more I would enjoy the park if I was with someone. I pass up concerts I badly want to see, miss exciting pop-up events in the city, and let my vacation days lapse — all because I don’t often have someone willing to tag along. It’s not that I want a boyfriend, but I want someone by my side, at all times — even if it’s just my dog. So if I feel that way living alone on an average day, surely those feelings would be amplified to an unbearable level abroad.
But then Tinder reached out to me, because I guess my singlehood is so apparent it’s on a public relations team’s radar. They offered to send me anywhere to test out their new Passport feature for traveling singles. This was my opportunity to go to a new city completely alone, knowing that I would be forced to get out of my comfort zone, and forge connections with strangers without a safety net of a friend or family member. It was solo travel without the need to actually be solo. And if I happened to meet the love of my life, two birds, one stone.
I chose Toronto in the hopes that a stereotypically friendly Canadian man would make my journey easier.
What is Tinder Passport?
The basic Tinder we all know and love and delete and reinstall is free, but the premium offering — Tinder Gold — costs $29.99 a month, with a price break if you commit to a six- or 12-month membership. Tinder Gold’s main features are the ability to undo an accidental left swipe, or browse guaranteed matches that have already swiped right on you. But one of the more appealing, lesser-known features is Passport, which allows you to swipe in other cities before you’ve arrived.
This has a multitude of benefits for regular dating. You can set your location to your home neighborhood to swipe at work. You can line up dates in New York City even when you’re stuck in your parents’ house in New Jersey for the weekend. You could test your theory that all the good men are hiding in Omaha. But the Passport feature is particularly advantageous for gregarious solo travelers who want to have a date waiting for them in another country before the wheels have even touched down.
I re-downloaded Tinder a month before my trip, glass of red wine in hand, and with it popped up the ghosts of old conversations that never panned out with San Francisco tech bros, and photos of me sporting a regretful bob. My bio still said I was new in town. It had been well over a year since I’d moved to the Bay Area, and just as long since I’d last used the app. I updated my photos to my current shoulder-length hair, unmatched with anyone lingering in my inbox, set my location to Toronto, and took a big swig of wine.
My bio now read: “Travel editor heading to Toronto the first weekend of August for a story. Need a nice Canadian local to show me around! Distant Trudeau relatives preferred.”
None of that, technically, was a lie.
My Tinder-cation begins
Sitting in the San Francisco airport on Friday, panic began to set in. Turns out, it was a Canadian national holiday the weekend I was heading to Toronto, and most men would rather be partying at their parents’ lakehouse than taking out a Tinder date with no long-term promise. My original goal was to see three men over the course of the weekend, but by the time I had to switch on airplane mode, I had just one date confirmed, with Matt.*
The saving grace to my one, lonely plan for a three-day weekend was Matt’s complete enthusiasm for showing me the city and an early-bird attitude. He invited me to breakfast at Lady Marmalade in East Chinatown, a neighborhood few tourists would head to first, at 9:00 AM sharp. He was taking his role as tour guide seriously and had a full day planned across the entirety of Toronto.
Matt was already sitting at the back of the restaurant with a coffee when I arrived, and a wave of relief set in that he had, in fact, shown up, and that he gave off an easy-going energy that I could imagine spending the whole day around. He was also undeniably handsome, and my type, even if he was just barely the same height as me.
Matt insisted that I HAD to order the eggs Benedict, the “best in the city,” as if he could sense my eyes wandering over from the fresh fruit crepe to the brie, avocado, and bacon Benny.
Already, this was going better than most dates I’d been on stateside.
Conversation flowed easily, since we had an entire city to talk about, and I was still under the guise of researching Toronto itself. He told me with glowing pride about the quality of life in Toronto, humble-bragged about owning his own gaming company, and talked about how he spends most of his free time walking around the city’s many green spaces. He complained about the high cost of living, but I had him beat with tales of San Francisco rent. He showed interest in my glamorous-sounding travel job, even though it was clear to me that he’d traveled far more places than I have, but was playing it cool to make me feel like the expert.
When the bill came, I was relieved to not have to play the credit card dance and overthink what it meant if we split, or he paid. I laid down my card and told him that was the deal for the day — he showed me around, and I let my company (read: Tinder) pay for the expenses. In signing the bill, I felt like the character I was playing, of the jetsetting journalist whose job pays for her every need, who collects men like passport stamps.
We started our walking tour at his favorite, lesser-known farmers market, Evergreen Brick Works — located in a former quarry way off the tourist trail. We grabbed iced teas and walked in the surrounding park to a viewpoint overlooking the city. Along the way, someone asked if we could take their photo. They then asked if they could take one of us. We awkwardly laughed and said sure, wrapping our arms around each other’s waists and posing like a couple. So now, I have exactly one more photo of us than I do of any of my last four boyfriends.
From there we wandered around the Distillery District, popping in and out of artisan shops, and sharing our long lists of favorite TV shows — a mutual passion — and our furious thoughts on the finale of Game of Thrones. We walked along the waterfront toward the iconic CN Tower, where I convinced him to ditch a cool local lunch in favor of being a total tourist, dining at the top of the tower in the revolving restaurant with 360-degree views of the city. That way, even he could experience something he’d never done, and probably would never do no matter how long he lived in Toronto.
We walked to Queen Street West, through Graffiti Alley, and admired the neighborhood’s abundance of street art. We passed by a pop-up called The Funhouse, the trippy kind of immersive art exhibit where you walk through a wardrobe to reach Alice in Wonderland-style rooms. We bought tickets on a whim and took pictures of each other interacting with the art for our respective Instagrams, free of judgment from grabbing that #content on a date.
This was the sort of spontaneous adventure I’d never had on a date back in my city, which is usually relegated to happy hour at some pretentious cocktail bar. More importantly, these were the sorts of experiences I miss out on in general, because I’m always waiting for someone special to do them with me.
Around 5:00 PM, a full work day’s worth of a date, our conversation started to slow down, and the mutual desire to call it quits was palpable. We’d crammed more experiences into one date than you would in months under normal circumstances. We’d learned far more about each other’s lives, interests, and dreams than you’d ever risk sharing on a normal first date. But there was nothing more to say, nothing more to show me, and thousands of steps around the city later, we arrived at the front of my hotel exhausted. It was clear we weren’t going to rendezvous upstairs, but how do you say goodbye to someone you’ve spent the entire day getting to know, that you have no intention of ever seeing again?
Quite simply, actually.
We hugged, I pecked him on the cheek, and thanked him profusely for showing me around his city. He wished me well with the story and the rest of my time in Toronto, I wished him a fun rest of the holiday weekend. He walked away, and for once, I didn’t spend the next few hours texting with my friends trying to dissect every moment, stressing over whether I’d get a second date. I just went upstairs, ordered room service, and went to sleep.
Taking the spirit of Tinder with me
The next morning, I boarded an early train to Niagara Falls. I wasn’t going to fly all the way to Ontario and not see one of the great natural wonders of the world. On Tinder, I was pushing hard for someone to join me on a Segway tour, but I settled for the promise of lunch with a tourist from New York in the kitschy downtown, after my trip on the Hornblower of course.
Niagara Falls is the quintessential couple’s trip. It’s the perfect mix of cheesy and romantic. It’s the setting of Jim and Pam’s wedding for God’s sake. It is, in other words, the exact type of activity that would have normally sent me into a panic attack for doing alone. I might be able to handle a work trip for a few days, but a cruise under the majestic falls, with dozens of couples with selfie sticks laughing and kissing in their ridiculous ponchos? It’s the sort of moment that used to make me think, if you didn’t share the memory with anyone, did it even happen?
But even the potential of having a companion for lunch, even if it didn’t actually pan out, was enough to make me feel like I wasn’t foolish for donning my poncho solo. Even the fact that I was wearing a cute outfit and makeup, instead of my usual lonesome look of yoga pants and dark undereye circles, made the occasion feel like just that — an occasion. Except I also didn’t have to worry about that makeup getting ruined from the mist of the falls.
My lunch date did end up hitting me with the sudden unmatch, a few minutes before we were meant to meet. But I was actually relieved to have the rest of the day to myself. That extra time meant I could go check out the 4-D experience (most definitely meant for children) that was included in my ticket. It meant I could FaceTime my parents and show them the view of the falls. It meant I could simply sit on the lawn and eat an ice cream cone from the Ontario-only chain Matt had told me about the day before with great enthusiasm. I could still enjoy shared moments, even if all I was sharing was the same favorite flavor of ice cream as a new friend.
I left Toronto with memories, untarnished by the anxiety of whether or not I had a future with my date. In the months that followed, I downloaded Tinder Gold again before my trip to Italy to practice my Italian with some locals. I hit up one of my Canadian matches whom I never met up with for the lowdown on the best poutine in Quebec City, his hometown. I even used it with the intention of actually dating again in my new home on the East Coast, this time with the much healthier attitude of no expectations for anything but a recommendation on where one can find good food in Delaware.
And as for Matt, we still follow each other on Instagram, throwing each other a cordial like every now and then. He even texted me a month ago to thank me for turning him on to Fleabag. I believe he’s still waiting for his local guide to Toronto to hit the pages of Matador, and for that, Matt, I apologize. We likely won’t cross paths again, but if I do find myself alone in Toronto again, I won’t be afraid to reach out. Because if this experience has taught me anything, it’s to relax and be open-minded for any outcome. Worst comes to worst, I’ll still have myself to keep me company, and turns out that isn’t the worst thing after all.
* Actual name has been changed.