I started dating in Montreal at 36 — Here’s what I wish someone had told me before

Dating is overwhelming (and that’s normal)

Is this first date going okay? Are we going to hold hands? Is this something that only happens when you’re in high school? Why is this so confusing? Scrap this, I’m not ready to date yet.

Dating for the first time at 36 is overwhelming.

You’re a grown adult, and yet you feel completely clueless. I was recently separated and on my way to being divorced. My ex was someone I met when I was 17.

I needed to understand what I wanted first. Did I want to continue being single? I liked my new life, new friends, new hobbies, and a new me, more independent and self-assured.

It had been eight months since my separation, and I still hadn’t signed up for any apps. I had never downloaded one in my life.

So yes, I had missed everything about modern dating. And catching up was no easy task.

Meeting people IRL is still a thing

A guy once asked for my number on Ste-Catherine Street.

Why is a strange man talking to me? What is happening?

I must have looked so disoriented because he asked if I was okay. I figured, what do I have to lose? We chatted for a bit, and I gave him my number.

Did I just give my number to a serial killer? He seemed nice. Also good-looking. I thought people didn’t do this anymore.

I texted my bestie my location to make sure I came home alive.

You’ll learn to trust your gut faster than you think

A friend offered to set me up with someone. “He’s a nice guy,” she said. “He’s a homeowner on the South Shore.”

“No, thank you,” I replied. “I’m not going to date someone living a boring suburban life.”

My friend said I was projecting too much and making this a bigger deal than it was.

Was I? I don’t drive, and just the thought of those cookie-cutter houses makes me nauseous.

And that’s when it clicked: I do know what I want.

I just have to listen to myself and trust my gut.

This was the moment I decided to join the apps.

Dating apps are a LOT

I was so lost, I turned to ChatGPT to see which dating app was best for Montreal. My friends later informed me that Hinge was the way to go.

Do I create my profile in French or English?

I went with English. Most people will switch anyway, and it helped me avoid the ultra-francophones who refuse to speak anything else for political reasons.

I created a profile and received an avalanche of messages.

Wait — why am I seeing messages about a threesome?

Oh. Wrong settings.

False code red. Breakdown avoided.

Scrolling through profiles was exhausting. Some bios were half-finished — next. Some said they were looking for short-term, whatever that meant — next. Guys living outside the island? Next.

Surprisingly, only a few guys were holding fish in their profile pictures.

Has that trend finally passed? What replaced it? I have no idea.

First dates are awkward

First dates are often awkward. And there’s just no getting around it.

One guy rated our date at the end. Weird.

Another told me his travel story involved getting lost in an all-inclusive resort. Snooze.

Walking dates on the Lachine Canal felt strange. At least pay for my coffee on the go!

The “rules” of dating will be confusing

What’s this two-day rule for responding? Why does everyone feel so unbothered and apathetic? Boring!

After how many dates do you sleep with someone? Three? Is there an answer to this?

Someone should have told me that having sex with people you go on dates with is mostly bad. Dating podcasts confirm this suspicion.