Jess Janz and With Strangers

There’s something powerful about creating spaces where connection isn’t just encouraged, but intentionally designed. For writer and community facilitator Jess Janz, that connection has been both a lifelong curiosity and the foundation of her work.

What began as a personal exploration of identity, belonging, and what it means to feel truly seen has evolved into With Strangers - a global community and series of experiences where people come together to connect in ways that go far beyond small talk.

In our latest At the Heart of the Community interview, we sat down with Jess to explore the origins of her work, her perspective on what community really means, and why creating space for meaningful connection matters now more than ever.

Photo Credit: Maiya Chan

You’ve created spaces where strangers connect in really meaningful ways - what first made you curious about human connection in this way?

I’ve always been curious about connection. I was a really deep-feeling, creative kid trying to make sense of the world, often wondering - does anyone else feel like I do?

That curiosity stayed with me. It started with a kind of intensity, almost an urgency to find connection, and over time it’s softened into something more like a calm curiosity.

At the core of it all is the understanding that humans are hard-wired for connection. We’re deeply relational beings - we need and thrive in community. I’ve always been interested in what it looks like to move beyond surface-level interaction and connect with people on something that feels real.

Do you remember a moment early on with With Strangers where you thought, “there’s really something here”?

From the very first dinner, it felt almost kinetically obvious that something was happening. There was this sense of - what have we tapped into here?

At the time, I wasn’t thinking about monetizing or building a business. I even joked that maybe this could be my job one day, but I didn’t mean it seriously. It felt more like an exploration - let’s just discover what this is.

It wasn’t until I moved to San Francisco that I really understood the weight of what I had created. Being in a completely new city, without my community, made me realize how much I had left behind. In Toronto, I had built years of connection without even fully recognizing it.

At the same time, I was working a corporate job for the first time and felt completely disconnected from myself. I remember thinking that no matter what my salary was, if I wasn’t making art or engaging in this kind of work, it felt like my soul was dead. That contrast made it clear that I needed to double down on this.

What does “community” actually mean to you?

Community is more nuanced than we often make it out to be. There’s a difference between being in community and building a community, and I think those lines can get blurred.

With Dinner with Strangers, for example, most people who attend are new. So while we’re creating an experience that serves the community, I don’t always define it as a traditional community in itself.

What feels more important to me is what people take with them. My hope is that people leave with a deeper openness - having gotten out of their comfort zone, shared honestly, and been impacted by someone they may never have crossed paths with otherwise - and bring that energy back into their own lives.

Community can be both big and small. It’s greeting your neighbour, supporting local businesses, offering a small act of service. It’s about being on the lookout for ways to engage with each other and actively contributing what you have to give.

What do you think people are really craving right now when they seek connection?

At the most basic level, we want to be seen.

We live in a world that’s so focused on productivity, outcomes, and optimization: networking, self-improvement, achieving something. But in that, we often lose sight of presence.

What people are really craving is the ability to show up as they are. To be present with one another. To be cared for, and to care for others.

There’s something really important about being open to whatever emerges in a moment. Sometimes connection is deep, sometimes it’s light or funny, but allowing space for all of that is what makes it meaningful.

Photo Credit: Maiya Chan

What’s one simple shift someone could make to have more meaningful conversations in their everyday life? 

I think there’s a real whimsy to connection that we sometimes overlook. It can start with very low-stakes moments - complimenting someone’s dog, introducing yourself to your barista, learning the name of someone you see regularly.

If you have places you go often - a coffee shop, a gym, a bookstore - you’re already part of that ecosystem. There’s an opportunity there to engage in a small but meaningful way.

At the same time, there’s a deeper layer to consider. Who are your people? And if you don’t feel like you have that yet, where might you find it?

The reality is, we do have to leave our houses, or intentionally show up somewhere, even online. That might look like joining a class, attending an event, or finding a space connected to your interests. There are so many accessible ways to do this, but it does require that first step.

We’re excited to be collaborating with you on an event May 3rd: With Strangers x She Summits: Joy, Conversation & Charcuterie at Two Rivers Meats in North Vancouver. 

Our event is centered around joy. How do you see joy and connection intersecting?

Joy is often misunderstood as something light or frivolous, but I actually see it as something deeply important. Joy can be an act of defiance.

Even in really difficult times, joy exists alongside everything else. It doesn’t mean things are easy or perfect - it just means we’re allowing space for lightness, care, and connection within it.

Joy relieves pressure. It reminds us that life isn’t just something heavy happening to us. And it’s not something we should wait for. We have to prioritize it.

Photo Credit: Maiya Chan

What kind of energy do you hope people walk away with after the event?

A lot of what I create is rooted in detachment from outcome.

People often come in with specific hopes - they want to make friends, meet someone, feel a certain way. And while those things can happen, the intention isn’t necessarily that you leave with a defined result.

It’s more about what it felt like to be in the room. To listen to someone’s story. To experience that specific combination of people and energy.

I hope people come in curious and leave inspired - by something they heard, something they felt, or something they didn’t expect.

For someone who’s never experienced With Strangers before, what can they expect from a night like this? 

It’s very introvert-friendly, which often surprises people. I’m an introvert myself.

There’s enough structure to guide you into conversation, so you’re never left wondering what to say. It’s a bit like a gentle hand-hold into connection.

The prompts are designed around storytelling, so you’re invited to share something meaningful, but always in a way that feels comfortable to you. You get to hear snippets of other people’s lives, and share your own, in whatever way feels right.

What would you say to someone who’s a little nervous to come alone?

Almost everyone comes alone - like, the vast majority of people.

That’s part of what makes it feel so accessible. Everyone is in the same position, even if it doesn’t feel like it at first.

Very quickly, you find yourself in conversation, and that feeling of being alone fades. You won’t leave feeling alone.

Learn more about Jess here, including her upcoming book, 'The Table Where We Meet.

Experience her work brought to life through With Strangers x She Summits: Joy, Conversation & Charcuterie on Sunday, May 3 (6:30–8:30 PM) at Two Rivers Meats.

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Jenn Wint and WINT Communications