‘What’s going on? How did we get here?’
This is what I thought to myself while I was stuck on public transport with my date, Kate*.
This was after awkwardly already ending it and saying goodbye to each other – then bumping into each other again on the way home.
The uncomfortable courtship clearly refused to call it quits.
This was in 2014 when I was 27 years old, after I downloaded OKCupid on my phone.
I have severe social anxiety, which significantly impacted my love life. Nevermind having a serious relationship, I’d never even been on a date before.
This was the first time I was putting myself out there. Don’t get me wrong, I wanted to meet someone. But my anxiety got in the way of me asking someone out.
However, a good chat over dinner with friends one evening in early 2014 gave me the motivation I needed.
I uploaded photos that were strategic and intentional – professional headshots and carefully selected pictures of myself when I was travelling. I wrote and edited my bio at least five times until I settled on something unique that captured my love for comedy, movies and sushi.
My outgoing messages to matches were equally carefully crafted, like cover letters, always starting with questions like, ‘Who’s your favourite character from The Office?’ or ‘What’s your favourite restaurant in the city?’
After months of endless swiping (which really felt like a full-time job), I finally met Kate in the dead of winter. We bonded online about our mutual love for cats and our shared taste in films. We hit it off; at least, we did on paper.
So, we decided to take the next step and meet up. I was definitely anxious but I bit the bullet.
A few days later during a snowy evening in February, we convened at a local coffee shop in Toronto.
I arrived first and I got us a table near the entrance so I could see her walking in. For the next five minutes, every time the door opened, I shot up in my seat, wondering if it was her.
Finally, she came in. I didn’t know how to greet her, so I reached out to give her, not a hug, but rather, a handshake. As if we were having a business meeting. Almost as soon as the tryst started, my anxieties kicked in – right on schedule. I felt like a chipmunk that just wanted to crawl back into his hole.
I quietly sipped my latte, not knowing what to say to this lady in front of me, a potential partner. We talked a little bit about work, but looking back, our entire exchange felt like a blur.
‘I’m sorry, I don’t know what to say,’ I repeated five times – I know, I counted. I felt like Kate was a little sympathetic, but I got the feeling she might have mistaken my anxiety for apathy. And unfortunately, I wasn’t open about my struggles.
One excruciating hour later, we agreed to part ways and officially ended the date, silently acknowledging that there was no chemistry between us and knowing we would never see each other again. I politely told her that it had been nice to meet her, and shook her hand again, concluding our business.
Like many people who live in Toronto and don’t drive, I rely on public transport. I walked back to the nearest subway station to head back home.
During the walk, I was in such a daze, ruminating about how the date had gone, that I didn’t realise that Kate had just passed me and was heading to the train station too.
But when I arrived on the platform, there she was, waiting for the same train. Destiny had thrown us together again.
‘Please don’t make eye contact,’ I repeated to myself silently.
But of course, we made eye contact. There was no avoiding her.
‘Long time, no see,’ I said ridiculously. And she gave me an awkward smile, looking far from thrilled at seeing me again so soon.
When the train arrived a few minutes later, we boarded it together, both of us heading north. We sat next to each other, but we didn’t talk at all. Total silence. The conversation had run completely dry.
After 10 nearly minutes on the train, we heard an announcement from the conductor who alerted us that there was a subway delay. Kate and I both looked at each other and groaned.
Apparently, there was a commuter on the tracks, which meant that there were no other trains heading north. Everyone had to get off.
And when we got to the station entrance, as the temperature was below zero degrees, Kate and I both turned the same way to the local coffee shop to plot our separate routes home.
Our desire to keep warm outweighed the awkwardness of the situation. Just about.
It was our second coffee shop visit of the evening. We still were barely talking, minus the odd glance to each other. I got myself a hot chocolate and she got one too.
Although, I mused to myself, as horrific as this felt, technically, this counted as a second date, right?
I didn’t drive so I called my dad, who came to pick me up. When he arrived and Kate was still sitting there, I awkwardly asked if she wanted a ride home. I was just being polite – I didn’t think she would say yes. But of course, she did.
I found myself sitting in the backseat of my dad’s car with a random girl I didn’t think I’d see again.
My dad happily introduced himself to my non-future wife and as, once again, we descended into the now-familiar silence, he, completely oblivious, smiled and winked at me in the rear view mirror.
The car ride lasted 15 minutes but it felt like a lifetime when we finally got to the girl’s place and dropped her off. We had a final awkward laugh and I thanked her for a ‘memorable’ evening.
Now, I know what you’re probably thinking at this point – this girl and I shared a subway delay together, and she even met one of my parents. We definitely got married, right?
Nope. I never saw her again. This was just a dreadfully long interaction with someone I had no chemistry with.
After that initial dating debacle, I found the courage to go back to OKCupid and had a few more first dates, mostly awkward, before my mental health took a dive.
Then, I took a break from online dating until 2020, when I finally met someone else, ironically in the middle of Covid-19.
Now, I’m engaged to this spectacular woman who – might I add – has met my dad and who I can sit comfortably with during a train delay.
*Names have been changed
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