TO in Love: the high-five


‘Toronto in love’ is a brand spankin’ new series where anonymous writers share their highs, lows & hilariously horrifying tales of dating in the 6ix.

A fifth date means something.

It means you’ve endured date two (the worst of all dates), and wanted to move on to the next round.

It means that you’ve told yourself that this person is worth your weekend night – that your inner circle and medium circle know this person’s name. Fifth date means that you don’t hate this person and you could potentially (or already have) slept with this person (you do you!). In my case, I hadn’t. Date four set the stage but I needed more time. Date five felt like the time.

Until, he high-fived me.

It didn’t take long for the night to take a turn for the worse.

It was a Friday. A really good Friday actually. I felt like things were maybe, finally, dare I say it? Going my way. That was my first mistake and will always be the mistake. Never think that things are going your way because it will quickly turn out they are not. Key learning.

So it was a Friday. I just got promoted. I had a date (a fifth date!) with a guy I didn’t hate and could actually see myself spending time with. How did things that were so right go so wrong?

I knew it was over the moment I saw him. We had some back and forth on where we should go, what we should do, because he had plans “post-date”. A younger me would have said “fuck this guy he’s not worth my time.” Older me was trying to be open minded.

Background on me: single, 26-year old female who has been dating for approximately five years to no avail. Used to have a laundry list of requirements and has year by year dropped this to one requirement: good teeth.

So, did it bother me that he had plans after our Friday night date? Of course. But, he still wanted to see me, and maybe we would have SUCH a good time, that who would care that he had plans. He would bail and hang with me.

He walked in late, I had just ordered a drink to pass the time. We didn’t hug. No part of our bodies touched and I felt in that moment that everything was wrong and how could I even have thought for one second that this person was interested in me? He asked how my day was, I had mentioned it had been busy.

“Well, today was actually pretty exciting – I got promoted,” I said.


“Cool – that’s great.”

No hug, no kiss, no cheers. He went in for the high-five. (A high five?!?)

There is literally no appropriate scenario in which to high-five your date. I think we can all agree high-fives should be reserved for your cute nephew, the student you tutor, your trainer at the gym and the guy that sits beside you at work, MAYBE.

As if it couldn’t get any worse. But that’s the thing about the mysterious world of dating – it can, contrary to popular belief, always get worse.

As I sat there ruminating in my pathetic post high-five existence, I wondered, is this real life? Only halfway through my second and what would become my final glass of wine, my date expressed his concern about catching the next streetcar out of there to his “post-date” plans. I rapidly experienced a range of emotions, first disbelief, then annoyance and finally a comfortably numb acceptance. Wishing he was already gone, I vaguely heard him utter:

“Well I’m going to catch the streetcar now because the next one isn’t coming for another 20 minutes.”

I glanced at my half full glass of wine. It wasn’t even 10 o’clock.

“I’m going to stay and finish my wine” I said.

He got up, I hugged him, knowing full-well I would never see him again in my life and happy about it.

As I sipped my wine and watched him make a swift exit, I thought, I guess I need to find my “post-date” plans.

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