Alyssa is a 34-year-old urban planner who lives in Church-Wellesley Village. She describes her style as “alternative-femme tomboy,” and says she is outgoing, but “in a reserved kind of way.” She likes exploring the city, hanging out with friends—usually doing something that involves food—and spending time with her dog. When Alyssa met Talia on OkCupid, she had been single for four months.
I didn’t know many people in Toronto, because I’m new to the city, so I thought I had nothing to lose by trying OkCupid. Being lesbian, I know that it’s weird to say that I’m actually scared of lesbians—too much drama; not enough living up to my possibly over-the-top standards.
There was only one girl I saw that I was instantly attracted to: She seemed funny, cool, and definitely beautiful. We messaged for a couple of days, texted for several more, and made each other laugh a lot. I think we both knew even before we met that there was something there.
Talia had also just moved to Toronto. We decided to meet for a Saturday-afternoon date. We both wanted to explore the city, and thought it would be a great idea to do it together. I arrived early at our arranged meeting spot in the Annex, and I could see Talia walking across the street. That’s when I’d usually get super nervous, but I wasn’t—I was just looking forward to hanging out with her.
I like to think that I’m a pretty good judge of character, and I usually know very quickly if a new person is a “yes” or a “no.” Within the first few minutes, as we made our way through the snow to Fresh, it began to feel like we’d known each other for a long time. Humour is a big thing for me; if you can’t laugh, life is going to be hard. Talia could take a joke, and she gave it back just as good. All the laughing we’d done during our week of texting spilled over into the date.
After lunch, we grabbed coffees and continued on, chatting and people-watching all the while. It felt very relaxed. We passed Honest Ed’s, went in to look around, and laughed about all the cool stuff in there. We looked through the clothes and picked out the craziest outfits we could find for each other. Later, Talia dramatically “saved” my life as I (embarrassingly) slipped on ice while crossing the street. She asked me if I liked musicals; I wondered if that was a trick question. I hate musicals! I said, “No, not really… at all.” She replied, “Excellent, I hate them, too.” I loved how she used that as an opportunity to test me—and I passed!
As the date progressed, so many of my way-over-the-top mental-checklist items were being ticked. It really felt as though her and I had instantly jumped to the fifth date. There was none of the first-date awkwardness, none of the “What the hell am I doing with this person, and when will this date just end?” stuff. It was exciting, but comfortable at the same time.
Before we knew it, three hours had passed, so we walked back to our original meeting spot and shared an awesome kiss. I left with a huge smile on my face, knowing that I had met someone I loved hanging out with—someone I could honestly see myself with for a very long time.
Alyssa rates her date (out of 10): 10
Want to be a dating diarist? Email email@example.com.