Connie is 36 years old, lives in Cabbagetown, and works in finance. She describes herself as serious and aloof at first, but laidback once she gets to know someone. (“I surprise people.”) She spends most of her time travelling for business or pleasure, but she also enjoys going to plays, skiing, and cycling. Connie had been single for five months when she met Maynard online.
I noticed that Maynard had looked at my profile a few times. His write-up really appealed to me, but I wasn’t keen on his location (Calgary) so I ignored him. One day, I got a message saying that he had added me as a “favourite.” I sent him a quick note to let him know that he was definitely someone I’d be interested in, but that he’d probably noticed my location preferences.
A few days later, I got a lovely (and lengthy) email from him. He explained that his location was transient, and that, at that very moment, he was on a train to Toronto. I replied that I was five minutes from Union Station. Later on, I got a message saying that he was sitting at a bar downtown, “wondering if this is how fairytales begin.” He added that he was going to be in town until “at least tomorrow or Thursday, or Friday, if Toronto inspires me—or a lifetime, if you do.”
I wasn’t sure if he was a genius or a douche; it could have gone either way. We found a time to meet for one drink before his dinner plans with some childhood friends.
I picked a bar close to his dinner destination on King West, and was drinking a glass of a Chilean Cabernet Sauvignon when he walked in. We had an instant, mutual attraction—Maynard was tall, dark, and handsome, just as his profile had suggested. He also turned out to be a kind, warm man, behind what could be perceived as a “Bay Street shark” exterior. The conversation was immediately sharp and fun, with plenty of banter. We’re both in finance, but we only briefly talked about work. We were also both surprised that the other person was single.
Maynard told me he regretted having such little time to spend with me, so he asked if I wanted to join him and his friends for dinner. My plan was to stay for just one drink, and then leave so they could catch up. Shortly before his buddies were due to arrive, Maynard took my hand, smiled at me, and said that he would really love to kiss me. The kiss was very gentle. We kept it tame given that we were sitting at a bar, but it was a very promising start.
Maynard’s friends were funny and down-to-earth, and their dynamic convinced me that Maynard was a good guy. I ended up staying for dinner. They said goodbye around midnight—having picked up on the vibe between Maynard and I—and he and I stayed until 2 a.m., drinking and kissing.
We went for a long stroll away from crazy King Street, holding hands and giggling the whole way. We talked about what we’d liked about the different places we lived, the pros and cons of thejobs available there, our take on the overall quality of life of the cities, and our future plans.
A quick drink quickly turned into seven hours. We kissed goodnight before he closed the door on my cab. We’ve been texting and talking almost every day, and he’s now planning his next trip to the T-dot.
Connie rates her date (out of 10): 9
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