dating in toronto

Toronto Dating Chronicles: a night out on King West doesn't lead to love

If there's one thing Toronto locals can relate to, it's the challenging dating scene here in the big city. After a three-year, no romance dry spell, I decided it was time to get back out there.

First stop, King West!

10:00 p.m. on a Saturday

It was a lively Saturday night, Ubers stopping and going; the streets were busier than usual.

We transitioned from hoodies and ripped jeans on Spadina Avenue, to city slickers adorned in sleek black dresses, heels, birthday sashes, and button-downs, contrasted with crossed-arm bouncers on King West.

We opted for "Toronto's Oldest Bar," also known as The Wheat Sheaf Tavern. Ten dollar cover, we walked in, immediately hit by hot air and a sticky bar essence.

The live music added to the energy, but the packed space left little room to move. After locating a booth only to be shooed away by an angry couple, we settled for a spot closer to the exit.

That's when "Mike" approached. He held out his beer, offering a toast. We talked about the night, the bar, and where he came from. He invited my friend and me to join him for late-night eats, and while we declined, I did give him my number.

1 Week Later

After chatting on the phone that week, I had a good feeling about Mike and agreed to go out. That Saturday, I received a text at 6:00 p.m. announcing his arrival, with the strange request asking if I could bring him moisturizer.

While confused, I agreed and brought him my poor father's Kiehl's hand cream. Mike lathered so much on his skin that he was coated in a white, gooey glob. I stared in confusion, "My skin gets dry after I take baths." This was definitely a first and very unusual date ritual to witness.

Mike drove us to our destination; Toby's Pub and Eatery, a spot on College Street — dimly lit and not too busy for a Tuesday night.

When the server arrived, I ordered a Long Island Iced Tea and Mike decided to have water. "That's all?" she said, "Yes!" said a confident Mike, "Isn't H2O the best!" he beamed. I agreed; I mean sure, I love water, but at a sit-down pub that's all you order? I tried not to judge, inflation hasn't been easy on anyone.

Our server returned and placed my iced tea and Mike's tap water down. He looked pleased, and I stirred my drink. Mike seemed hurt that I chose liquor, "Am I that awful to be around?" he whined, "No, no!" I said. "But we're at a pub, I thought one of us had to order a drink."

As the night continued, Karaoke was just getting started. The pub began to fill up and people moved to the front to add their names to a Karaoke list.

We watched as they sang the usual, "Sweet Home Alabama," "Bohemian Rhapsody,""Man I Feel Like A Woman," et cetera. Groups of friends sat at tables eating fries and nachos and drinking pitchers of beer.

Mike pulsated in his seat, vibrating like one of those energizer bunnies. His name was called. "Wish me luck," he winked and bolted to the mic. I scooted over in my booth to get a better view.

The beat of "Ice Ice Baby" began to play and he belted out the lyrics, stomping around the room, making his way through the aisle. "Wave your hands people!" he screamed as though it was his concert. Mike stomped and hopped, making the floor shake with each step.

His facial expressions showed that Karaoke was not fun, but rather business. Grabbing a customer's water, he poured it over his head, energizing himself even more. My jaw was on the floor.

His performance ended and we all clapped. "Water!" he called out, "Can I get another water, please?" Mike was parched from his performance. The server nodded, and I rolled my eyes. When she returned with the bill, it was placed in front of the soaked shirt wonder.

There was a long pause between Mike and I. Who was going to pay? After an excruciatingly awkward silence, I placed a twenty down, and Mike had one last sip of his ice water. My one drink was fifteen dollars. Jeez, I thought to myself, Toronto has seriously gotten expensive.

This was an odd experience to say the least. Is meeting someone at a bar the right move? Should I buy my father a new hand cream?

I must say as bizarre an experience this was, I'm grateful for the laugh, the story and lesson. What's your go-to spot for meeting people in the city? The gym, the library, the museum, dating apps?

Perhaps, I must broaden my horizons and meet potential matches elsewhere. As for "Mike," I don’t intend for our paths to cross, but I wish him all the best in his musical endeavours.

Stay tuned for more Toronto dating adventures!

Lead photo by

Hector Vasquez


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