From Strangers to Soulmates: Why Saying Yes to Play Might Change Your Life

When I moved to Toronto in my early twenties, I only knew a handful of people. 

Fresh off a life-changing year traveling through Africa and coaching skiing in Whistler — where every day was filled with connection, adventure, and playing with strangers who felt like instant friends — I arrived back home and realized that real life felt… quiet. I had a job. I had an apartment. But I didn’t have a community of people. 

And honestly, I didn’t know where to start.  

I searched for a fun soccer league in hopes of meeting new friends, but the only leagues I could find were competitive women’s leagues and quite literally “out of my league”. 

What happened next was the beginning of something big. I had heard about adult social sports leagues in Chicago and San Francisco, so I decided I should try to start something similar in Toronto. 

I started JAM (formerly Toronto Sport & Social Club) because I believed there had to be more people like me — people who were new to a city, or maybe just stuck in a routine, and wanted to meet new faces, have fun, and feel a sense of belonging. I didn’t want anyone to feel like they had to wait for a friend to invite them out or be an elite athlete to keep playing. I wanted them to have a reason to show up — and to walk away feeling like they were part of something.  

Within months of starting the leagues, I felt I had an incredible community of friends, and I was witnessing others forming friendships and special relationships on the sidelines as well. 

All these years later, that’s still the heartbeat of JAM: connection through play.  

One of the things I’ve loved most about my work is watching teammates start as strangers and slowly — although sometimes it is almost instantly — become each other’s people. I’ve seen high-fives turn into Friday night dinners with groups of new friends. I’ve seen post-game chats become inside jokes. And I’ve seen many relationships blossom into marriages and full families – whose kids (now young adults themselves) are playing with JAM generations after their parents first met playing in our leagues. 

I shared a few of these stories in my book It Pays to PLAY. There was a couple who met playing softball, went on to get married and had many of their teammates in their wedding party. And another pair who met on the ultimate field and now have a couple of daughters both of whom love to play frisbee with their folks. And there’s the woman who moved to a new city, was incredibly lonely with no connections and she shared with us that “the leagues saved my life”, because she made lifelong friends by showing up to that first game. 

Stories like these still give me chills – this is my favourite part about the work we do at JAM.

But you don’t need to fall in love to find love in this kind of space. The love can be in the laughter. In the shared playlist before the game. In the person who remembers your name and asks how your week went. In the teammate who hypes you up after a not-so-great play. In the post-game patio conversations that start light and end deep. That’s what makes playing together magical.  

I still fondly recall a heart-to-heart conversation with one of my ultimate teammates after a game.  It was the late ‘90s and we had just finished playing, and we were driving to meet the rest of our team for some nachos and beer. He shared with me in the car that he was coming out, and he was debating whether to share this with the rest of our team.  I assured him that everyone on our team loved him unconditionally and had no judgment around his sexual orientation. Witnessing him open up to the rest of our team later that evening was so powerful. He felt comfortable doing so because of the bonds of friendship that had developed on the field of play. 

At the end of the day, play is just the vehicle — it’s the connection that’s the real prize.  

And let’s be real: it’s easy to stay stuck in our routines. To hang out with the same people, go to the same places, keep things simple. But I think we all have moments where we crave something more — a new energy, a new challenge, a new circle.  

That’s why I keep coming back to this message: Say yes to play. Even when it’s awkward. Even when you’re not “good” at the sport. Even when you must show up alone.  

That yes might change your entire experience of a city. It might introduce you to someone who becomes your go-to person. It might give you the confidence to try something new, to take a chance, to put yourself out there again.  

I’ve seen it happen — thousands of times.  

And I am not writing this to try to “sell” anyone on joining a league; I write this from my firsthand experience. Because I know what a difference it can make when you start to feel like you belong somewhere. It just so happens that sometimes that feeling can start by lacing up your shoes and showing up! 

So whether you’ve lived in your city for twenty years or twenty minutes, whether you’re outgoing or introverted, competitive or just-in-it-for-the-t-shirt… you’re invited. Come play. Come connect. Come find your people.  

You never know where one season, one team, one Tuesday night volleyball game might take you.  

Come solo. Come with a friend. Come exactly as you are. We’ll meet you at the field. No pressure – just play!  

Why force the issue?

Companies around the world are forcing their employees back to the office, against their will.

Remember when your Mom forced you to wear a dress but you wanted to wear jeans, or when your Dad forced you to take a nap and you weren’t tired? 

How happy did you feel being forced to do something against your will? 

With the pandemic behind us, some companies are starting to force their employees back to the office 4 or 5 days a week. 

Over the last few years, millions of employees in companies around the world learned how to productively contribute to the operation of their organizations while working from home and we learned there were some upsides including; more time for sleep, exercise, hobbies, family, and friends.   

  • We also felt some potential downsides to remote work, including a lack of mentorship for new or junior teammates and a lack of in-person human connection which can potentially negatively impact culture (although it doesn’t have to).  

But why force people back against their will? I believe with a little creativity there are flexible solutions that will help meet the needs of both employees and the organization.  Consider: 

1. How many in-person days are really needed each week? 

  • Instead of mandating 4 or 5 days a week in the office, consider might 2 or 3 days suffice.  
  • This flexibility will ensure some in-person human connection happens and provide time for some in-person mentorship and coaching, while also providing occasional upside of remote work 
  • Some employees will still opt to be in person 5 days a week, but others will appreciate the flexibility of choice 

2. Provide full remote work flexibility and autonomy two months a year.

  • Why does your new in-person work schedule need to be for the full year?  
  • Why not provide your team the option to choose two months each year when they have full flexibility to work from wherever they choose?  
  • Some will prefer the same routine – while others, may take this opportunity to work from a family cottage in the summer, or perhaps opt to live and work from a foreign country for a month or two.  

Of course, certain rules may need to be put in place around booking and planning people’s schedules in advance, but providing options will have your team feeling respected and also ensure that in-person mentorship and camaraderie occur throughout the majority of the year.   

As the owner of my own company, I’ve been enjoying the flexibility of remote work for over 15-20 years now. And now that my team has gotten to enjoy the same flexibility and shown themselves to still be passionate about our purpose, share our company values, and drive towards our vision, I feel it would be rather hypocritical to take this flexibility away from them. 

Organizations that choose to force their employees back against their desires, with little flexibility or options, will inevitably lose good people to their competition. 

Companies with great workplace cultures, know to treat their people as priority.

To watch my video on this topic click here: https://youtu.be/UX8wLF6b0Ng

PLAY creates lives.

PLAY creates friendships…and lives! 

Levi Cooperman is the co-founder of FreshBooks, that little Canadian start-up that achieved unicorn status a year or so ago, and he credits playing with JAM for his marriage and beautiful two daughters. 

Here is the story, in Levi’s own words: 

“It was the summer of 2003 when Naama and I first started playing ultimate frisbee together with JAM, and that team sparked our relationship. 

I believe it was a Tuesday or Thursday night team, and I think it was one of the first iterations of our team called Banana Cream Pie.  I invited Naama out to play and I don’t think she had ever played ultimate before then.  

We obviously hit it off on the field and, of course, even more so when socializing at the pubs over nachos and beers after the games.  

We started dating that fall and were never apart from that point forward. We got married in the summer of 2007 and now have a family of four. I’ve always been a loyal player and a big fan of JAM!” 

In addition to playing with JAM on a personal level, Levi, and his team at FreshBooks, have always cared deeply about the culture and their people finding ways to integrate play into the workplace. 

Over the last decade, FreshBooks has provided its staff with the opportunity to play a variety of sports like dodgeball, floor hockey, and softball on company teams in our JAM sports leagues. And they have also participated in several JAM virtual team-bonding events like Scavenger Hunts, Trivia and Survey Says. 

It is no surprise that FreshBooks has been recognized with many awards over the years including making the prestigious Canada’s Top 100 Employers list, being certified as a Great Place to Work – Canada, and being named to Greater Toronto’s Top Employers list.  

This intentional commitment to play has provided FreshBooks with a great opportunity for their team to strengthen friendships in the workplace, and it helped Levi find the love of his life! 

Levi’s story is not unique. Over the last 27 years, thousands of marriages and beautiful relationships have formed, and in turn, babies have been born, thanks to people connecting through play with JAM over the last 27 years!  

Wanna feel all the feels of more of JAM’s love stories? Read more from a sampling of our favorites here: www.kristiherold.com/lovestories

And if you know someone who met their love match playing with JAM (formerly Sport & Social Club) please share in the comments below – we would love to hear more!