Dating Diaries: She Just Bought A Luxury Car And I’m Still A Hustler- Josh’s story

Josh is a 33-year-old lawyer who “recently jumped into the fray of dating, online and otherwise.” He describes his style as “preppyish, slim-fit clothes, some Banana Republic, coloured shoelaces.” Josh says he is “outgoing, friendly, and caring” and likes “cycling, playing squash, going for beers with friends” and adds “At this point, going on dates is starting to be fun for me.” Josh says he is looking for “someone who challenges me, is physically attractive, and is ambitious, loyal, and caring.”

Susan and I were set up through a friend who thought we might like to meet each other. We each agreed after we got to see each other’s photo. I trusted my friend, too. I was excited to meet someone new who I didn’t meet on a dating site or an app. I’ve been single for about a year, but I’ve been dating. Susan and I texted for a few days first, to make sure there was mutual interest. It turned out we both enjoyed making pizza and cycling. For me, that was good enough to justify meeting in person.

As a relative newbie to the dating scene, I was way more nervous going into the date than I thought I would be. The plan was to have a casual date. We were going to grab a beer at Bellwoods Brewery, which has a great vibe, and allows you to have a private conversation. It’s also in a cool neighbourhood. Then, we were going  to grab some pizza.

Bellwoods Brewery is busy on Fridays — shocker, I know — and on a chilly winter night, that means you wait outside in the cold. While the heating lamps were helpful, it still made for a bit of a cold night. Susan was a few minutes late because she was finding parking.

She wasn’t what I expected. It’s funny how after seeing one photo, my mind begins to fill in the blanks. Doing this is probably a sign that I’m something of a dating novice. We talked about our families, careers, and why we choose to live in the neighbourhoods we’re in. It wasn’t a completely forced conversation, but it also didn’t have a natural flow. We didn’t really have a “feeling” for one another, and I had the sense that she was guarded with me. Admittedly, this is probably normal for a first date — I’m still somewhat new to this. Our lack of chemistry probably ensured that we wouldn’t move past the traditional first-date “topics” and move onto any high-level issues.

As the night went on, it became apparent that we weren’t really in the same place: I love a good Saturday night out with friends at the Cadillac Lounge, complete with the Sunday morning hangover. Susan and I are the same age, but she mentioned a few times that she doesn’t go out like she used to, and often stays in on the weekend. Also, it turned out that there are very different definitions of “liking” cycling. I commute on my bicycle far into the winter, and log something like 2,000 kms a year. She goes out on occasional Sunday rides when the weather is nice, but otherwise drives everywhere. Obviously, something like this isn’t a deal-breaker, but it showed that we were on different pages.
It’s not that I didn’t like her. I really liked that she was settled into her professional life, and that she was very comfortable with what she was looking for in a boyfriend. I was inspired that she had reached this stage in life, because it made me realize that I’m not there yet, but will be at some point.

Eventually, we touched on money and spending. Having been in law school for a while, I still struggle with spending even nominal amounts on “luxuries” like a cappuccino, always clinging to the idea that the bottom is going to fall out and that I’ll be back to my student lifestyle in the blink of an eye. She couldn’t relate. Actually, she told me that she had recently purchased a luxury car! At that point, date night was done.

She’s a nice person, and I hope she finds someone. It just won’t be me.


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