How They Met: Toronto’s top sexologist on finding true love

Whether it’s through her regular Cityline segment, her Sex with Dr. Jess podcast or her speaking appearances around the world, Toronto relationship expert (and former Post City columnist) Jess O’Reilly has been helping couples for decades. Now she gives us the scoop on the secret to marital success with husband Brandon Ware.

How they met

We met as students in 2001 while working at Hotel nightclub on Peter Street. I was bartending and Brandon was the bar back. 

The first date

We didn’t have an official first date. We hooked up after work one night and moved in together a few days later. That was almost 23 years ago, but it feels like a hot minute. There wasn’t really a chase or courtship, but I was the initiator. 

It was a turbo relationship, but we were young university students, so we weren’t overthinking or analyzing it. Having said that, we both remember the early days so clearly: Lying on the grass in High Park and saying “I love you” for the first time — probably a week after we met! And working late nights in the bars and eating sandwiches from Rabba while watching Law & Order at 4 a.m. 

The proposal

We were 23 and 25 when we got engaged and it felt more like a formality than a question. We were already living life as though we’d spend it together. Brandon tried to pop the question at Edwards Gardens. An older lady was watching and said something like, “Oh. You’re going to ask her now!” as soon as he got down on one knee. So she technically proposed for us while we were both crying.

The wedding

My family is from Jamaica, so we were married in Negril in 2006. It was so much fun! 

Shared hobbies and interests

Our lifestyle often revolves around my speaking schedule, which works well for us. We’re always on the move, so we make it fun and always carve out time for food, drink, art, nature and culture wherever we land. In February, I have work in Barcelona, Toronto, Bermuda, D.C., Miami, San Diego, N.Y.C., Bahamas, Cancun and Madrid. Brandon will join in most cities, so we’ll get to take in something new at every stop.

We also work together [Brandon co-hosts the Sex With Dr. Jess podcast] and are involved in a number of investment and start-up projects together, which isn’t a hobby per se, but definitely a shared interest. 

The secret to success

Because my work focuses on relationships, we’re always a bit reticent to share our “formula” because what works for us may not work for others. Having said that, we think a big part of why we’re so happy is that we each genuinely want one another to live their best life ever, so we’re open and flexible in terms of: needs and expectations — we don’t expect perfection or for every need and want to be fulfilled and we talk about what we’re feeling with ease; gender roles and all the baggage that comes with them; time and schedules including spending time apart; fluidity of the relationship; sex — we can talk about anything without judgment.

And we have fun together. We like each other. It sounds simple, but we’re really kind to one another.

Balancing careers and a relationship

It’s pretty easy now because Brandon has the flexibility to travel and plan around my work/travel schedule, which makes life fun. Because we don’t have kids, it’s definitely easier to balance work and pleasure. But I work with so many happy couples with kids who also find this balance, so it is possible for parents too. 

The future together

We want more of the same. We now spend time between Toronto and Barcelona and we’re on the road a lot for work. We’re hoping it lasts forever.

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