Jenna is a 27-year-old waitress who lived in the Annex until she moved to France last fall. She describes herself as loyal but easily bored, and says she is “popular with different groups of people, and able to get along with just about anyone.” For fun, she likes to ride her bike—“I miss winter biking in Toronto, oddly enough”—and going out for drinks. “Surrounding myself with good people is important to me,” she says. Jenna’s type of guy is “motivated, active and willing to take the initiative.” She met Matthew just before leaving Canada.
I went to grad school in a small town, so my love life was non-existent until I moved to Toronto and started to work at the restaurant. The dates started to flow shortly after that. I was relieved, because I refuse to try online dating. I still believe in the traditional ways of meeting people, and I’m not into the idea of meeting someone on a computer screen.
One afternoon in the summer, it was slow enough at the restaurant to stand around and watch sports highlights on the TVs that surround the bar. A tall guy walked in and sat down alone. I went over and took his order for a beer. Since he was one of my only customers, we started chatting and found out that we had a lot in common. In about 15 minutes, we had talked about where we grew up, landscaping, architecture and our shared love for biking. That gave Matthew a good opening to ask me to join him on a bike ride. He seemed a bit hesitant to be asking me out while I was on the job, but I was flattered and excited. I was leaving for a job in France three weeks later, so I felt like, “Que sera, sera!”
A week later, we met at the corner of Bathurst and St. Clair on our bikes. Matthew looked even cuter than he had at the restaurant. He rode a few feet in front of me as we headed to Mt. Pleasant Cemetery. In most circumstances this would be an odd place for a first date, but it is lush, tranquil and quiet, and has great paths for biking. I felt really relaxed and we talked about all kinds of random and personal things, including my upcoming trip.
Eventually, we biked out of the cemetery. Our ride took us to a bar, where we sat on the roof-top patio and had some appetizers and drinks. The conversation never lagged. When we were done, I decided I owed Matthew something special, so I took him to my favourite place for dessert, Dutch Dreams.
We ended up swapping ice cream cones after trying each other’s flavour and deciding we liked it better. I thought that was very cute. We got back on our bikes to ride home and Matthew asked if he could kiss me goodbye. Then he leaned over the handlebars and we smooched. I hadn’t had that much fun on a date in years. In the few weeks before I left for France, we had more bike rides, more ice cream and lots more kissing.
Jenna rates her date (out of 10): 10
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