Sheila is a 30-year-old graduate student who lives outside of Toronto. She says “My style is practical. I love the feeling of putting together a cute outfit from items that are already in my closet.” She is “ambitious, passionate, fun-loving, and kind.” Sheila loves watching sports and reality TV, and “keeping up with the news of the world.” She recently left the city to pursue her studies, but says “I keep my eye on the Toronto dating scene.” She is looking for “a confident man, who is emotionally available, values an independent woman, and who makes me laugh.”
I met David on a dating app. We had really engaging chats, so I was looking forward to the date we planned. He was intellectual, quietly confident, and older than me.
But, before I could get to David, I had a date with Alan on my calendar. I also met Alan online. He was funny, relaxed, and athletic. I was less interested in him than I was in David, based on our conversations, because Alan wasn’t very articulate over text. I find abbreviations like “hmu” to be a turnoff. But, he asked me to meet up for a coffee on a Saturday, so it was a pretty effortless situation that was easy to say yes to. Plus, I hadn’t been on a date for a while, and I figured that a little practice wouldn’t hurt before my “real” date with David.
It wasn’t my style to date around, but I’d heard so many dating experts, matchmakers and self-help gurus encourage women to date several guys at once until they have the exclusivity conversation. I figured I could give it a try.
When I saw Alan, I felt mostly neutral. He had nice eyes and a nice smile. But, from the get-go, he made me laugh. We just hit it off effortlessly. He was warm and charming. It probably helped that I was focused on David, and didn’t have a lot invested in the date, or in impressing Alan.
We had a great coffee and hang, and I was hoping to see him again. This was supposed to be my warm-up date, but it complicated the way I felt about David — who at that point, I hadn’t even met! Alan asked me to hang out again and I said yes.
My first date with David was a few days after my first date with Alan. It was also a great, fun date. With both guys I felt like different versions of myself, which was both exhilarating and frightening. Which version of me did I like better? Which one was the real me? It felt like an existential crisis.
I was totally conflicted. But, a few days after that, Alan took me hiking and then out for some food and drinks. It really sealed the deal with Alan. He brought snacks and picked me up like a gentleman. We had so much fun in nature, chatting about work and future goals, and having all the silly conversations that make dating fun. It was a perfect, sunny day. We had a really meaningful heart-to-heart conversation about family and what matters most to us. It was really special. I appreciated his ability to be open about himself.
I felt totally relaxed and comfortable, but I also felt butterflies. I could see us building a relationship that not only had the chemistry but had the friendship and ease to it that I had hoped one day to find. I remember thinking, “Just enjoy this moment!” because it was one of those days where the stars aligned and everything felt heightened. As Alan leaned in to kiss me at the end of the date, I knew he was the one I wanted to pursue. I called things off with David after that.
But, a few days later, Alan dumped me, because he wanted to date another girl. Was I just beaten at my own game? Did I just get a taste of my own medicine? Looks like yes.
Going from having two guys to zero guys really quickly felt like failure. So, I did what any good millennial does after this kind of heartbreak: I went to a festival, got drunk, and made out with a random stranger who turned out to be an anti-vax Trump supporter.
Sheila rates her date (out of 10): 9
Have you been on an amazing first date? Did your friend set you up with someone truly awful? Did you surprise your partner with an epic anniversary date? Email [email protected] and tell us about your best, worst, weirdest and wildest dates for the Dating Diaries column!
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