My Last Five Dates: A Private Restaurant, A Helicopter Ride, and Finding Love on Clubhouse


Before Covid-19 put all of our social calendars on hold, my dates were extravagant. In a normal year, I’d split my time between four major cities in Canada and the US, which gave me a vast dating pool. But even with options, I still moved in ways that honored what I wanted: a healthy relationship.

I approach my dating-life the same way I approach my career—with purpose and clear intentions. Let’s face it, a lot of us have been given bad relationship advice over the years. We’ve been told to pretend we aren’t interested, or to play hard to get to find love. But I have never understood saying things that contradict what you actually want. So I’m strategic. I’ve been paying for the premium version of dating apps for years, able to see who swipes on my profile first so I can narrow down options and avoid swiping forever. I’m also clear in my bio—I’m dating to meet my person, not just to pass my time. And it’s been amazing.

Date 1

Let’s call him Adam. We met on Hinge. He was funny and insightful. The kind of person you could have endless conversations with. For our first date, he rented out an entire restaurant for me tucked away in the Distillery District in Toronto, so that it was just him and I. This gave us the opportunity to get to know one another, in an intimate but public setting. Plus, a crowded restaurant on a first date can be overwhelming and make conversation that much more difficult.

Date 2

On my next date (with a new guy), I actually rented a helicopter and took him out on a tour of the city—he had just moved and I love an extravagant date. Again, this gave us alone time together in ways that gave us privacy, without losing the wow-factor I love so much. When you’re trying to get to know someone it can be so tempting to invite them over to just hangout, but I love to see effort. It’s how I know a person is interested and it gives me a signal to respond accordingly.

Date 3

Then there was NY-bae. We broke up right when the pandemic started because I knew there was no way I was getting on a flight anytime soon. And it was hard. This was a person that I loved spending time with but couldn’t anymore without putting the people that I loved at risk. But something that I learned in my ten years of online dating is to adopt an abundance mindset. There are so many people out there looking for someone exactly like you. Holding onto something that no longer works is a disservice to yourself, that person and the moments you shared together.

Date(s) 4

In lockdown, things changed. Only, they really didn’t—at least not in the ways I had anticipated. Sure, my dates changed. I wasn’t flying across the country anymore or being whisked away on extravagant first dates. But the quality of conversations made where we were irrelevant.

Covid-19 shifted how we connect. It created space for us to slow down and hear each other at a personal level, without the background noise we’ve become accustomed to. I’ve spent hours having soul-nourishing conversations with people that would normally take months to cultivate. I have had remarkable dates, even while following strict social distancing guidelines. One person I was talking to consistently went out of his way to care for me in my love language. He would drop off “date-night” packages, arrange to have my car picked up and cleaned, and spend hours on the phone with me.

Date 5

And then, I met my current partner.


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