Notoriously Known

Set-ups feel like they are something of the past. As the years age and working-from-home becomes more known, meeting others organically or through friends seems further from the norm. Yet, here I was, in the middle of a set-up.

He was a friend-of-a-friend-of-a-friend! There were a lot of connections that made this blind date possible, including my friend being the middle person. She did say, “I know nothing about this guy besides my friend vouching for him.” Since her friend was a woman, I thought I could trust this vouch from a stranger. Little did I know, I was about to learn an important lesson.

Let’s call my blind date Mr. Darkside.

“It took him a month after I gave permission for my number to be passed on, but he finally texted and we had a date planned. I wasn’t necessarily attracted to the photos I had seen, but as the rom-com professional, Kate Hudson, put it, you should always date outside your type! When I eventually saw him in person, I was pleasantly surprised. Maybe Queen Kate was onto something.”

I saw Mr Darkside from a distance and as we closed the gap between us, I gave him a hug. It was an awkward hug that made me wonder if he was awkward himself or just wasn’t a hugger.

We walked into the cafe to find one of my friends working behind the counter. I introduced them briefly while my friend and I did a quick catch-up. After ordering my drink, he hesitated before ordering his. I noticed that he wasn’t jumping at paying either, but my rule is if you ask me on a date and choose the place, you pay. This changes later on when dates become many, but for a first date, particularly a blind date that Mr Darkside fully initiated, it made sense for him to pay.

This is one of Kaila’s Dating Rules.

Normally, I hate uncomfortable situations and leap to fix them, but today I wasn’t having any of it. I just let the awkwardness float in the air. He eventually ordered and pulled out his wallet to pay for our coffees.

“Romance was in the air with a live string quartet playing in the cafe, setting the scene for what I hoped would be a successful set-up. As we walked up the stairs to the second floor, I heard a man’s voice call my name. As I rounded the staircase, I saw my former neighbour.”

We’ll call him Icebreaker. I also had some interesting encounters with him in the past, but we’ll save those for a different time. Icebreaker reached out to me and pulled me in for a big bear hug, talking about how great my hair looked and how it had been too long since we last saw each other. Being caught off guard, I quickly introduced Mr Darkside to get the focus off of me. Another woman in the cafe walked over to us all and said to me, “Weren’t you at the market this morning? I remember you because I liked your style!” 

To say I was stunned by this unexpected attention would be an understatement. If I wasn’t trying so hard to fill the awkwardness, I probably would have actually been speechless. After a couple of pleasantries, I swiftly moved us to a table with a view and said goodbye to everyone. I’m not sure why, but I apologized to Mr Darkside for “all of that” and explained that “that’s not normal.” He seemed annoyed and I don’t think he believed me.

What can I say? My life is like a sitcom. At least it is according to my friends.

Finally, we found a table to sit and our blind date officially began. Or should I say meeting! I learnt a lot about investment, which he deeply disliked but was adamantly pursuing. I learnt a lot about his friends (at least the one who set us up), and how he disliked everyone else. I also learnt a lot about how hard he was trying to figure out what he wanted from life and in his career. As a 40-year-old, I had expected he had found some form of work-life balance, but then again, life happens and everyone beats to their own drum.

“After learning all about him and asking multiple questions, he all but asked me one question. It’s as basic as they come.

’What do you do for work?’”

After an hour and half, I ended the meeting (I mean date). He mentioned meeting up again and then we said our goodbyes.

I have another rule and it was causing me to feel conflicted. This one states that unless the person has been disrespectful or has made me feel unsafe, a second date is in order. Nerves cause people to do weird things on first dates (ie. overtalk)! Whereas a second date gives opportunity for nerves to calm down and the true person to emerge.

So, instead of going with my gut that said this was going nowhere, I texted Mr Darkside and thanked him for the date saying, “I had a nice time.” That was a lie. We continued to text a little over the coming week, though I already suspected things weren’t going anywhere when his text after our date read, “It was really pleasant chatting with you :).”

I feel like pleasant is so bare minimum that it doesn’t always register as positive.

“After five days and no second date on the horizon, I texted saying, “I’m not sure where your head is at, but I get the feeling that you may not be interested or have time to go on dates. And that’s totally fine! Just let me know.” I’m not sure why I do this with guys that act like this. It’s like I give them an easy out. I should just move on with things, but I always fear I’m not being nice, so I over communicate like a fool!”

He replied letting me know he had some existential realization about dating and needed some time for “solo self love.” Whatever that means, but sure sounds creepy. I normally reply to these comments with a “good for you” and “take care”, but there’s nothing I dislike more than my time being wasted. So, I let him know that I wished he had come to that conclusion before he texted me to ask me on a date. I didn’t hear from him again.

Until…

I ran into him on the street while on an (angry) mental health walk. I pretended he didn’t exist. Mainly because I was on an angry mental health walk! And by pretended, I mean we literally walked past each other and I stared straight ahead. I guess my fear about not being nice had gone out the window that day!

But wait! There’s more…

A couple days later, I caught up with some friends and told them about my latest dating adventures. When I mentioned where My Darkside worked and his name, there was a universal gasp across the industry (or at least that’s how it felt).

“He was notoriously known in the city for being the worst boss and making women cry regularly at work. He was also supposedly “let go” from one job for misogyny.

Again, I was stunned, and in the words of my sister, I ‘dodged a bullet with that one!’ ”

Editor’s Note: A month later, I showed up at a bar to watch a game with some people, including my friend who had done the set-up. We had not spoken about it up until this day and I was nervous she would be bummed that it didn’t work out. The group collectively was engaged as I told the tales of this blind date and it’s quick downfall. My friend was floored that another woman would speak so highly of a man so notoriously known. Surprisingly, one of the strangers in that group also knew of him and his behaviour.

Once again I dodged a bullet and, once again, I learned the lesson of prioritizing listening to my gut! It’s now been added to Kaila’s Dating Rules.