What I Learned From Accidentally Building A Third Place

Everything from why I started this, my thoughts on making meaningful adult friendships, and other reflections as the first stranger of Stranger Conversations.

How this community all started

When Stranger Conversations first began, we did only one thing: inviting people who had done something a little unconventional to share their personal stories—unfiltered, relatable, interactive and unscripted. After all, I didn’t call this Stranger Talks.

Strangers on Empress lawn.

Before we had a ‘Third Place’ of our own, we’d host such chats wherever we could find space. One evening, there we were—twenty-five of us—sitting on giant picnic mats on the lawn in front of Victoria Concert Hall.

The sharing proper ended at half past eight, but the strangers lingered until the last train home.

Everyone had spontaneously self-organised into little circles of three to five: What brings you here? What’s your background? What are you interested in? Before long, we moved on to deeper topics like purposeful work, burnout, questions of spirituality and meaning, struggles with close relationships, ideas for side projects and more.

The topics were diverse, and yet they ran along a common thread: We’re still figuring things out and we’re not alone.

Even the invited guests blended into the crowd, becoming listeners who were part of the conversation. Everyone had become the protagonist of their own story. As I moved from circle to circle, I marvelled at all the different sides of themselves that people were willing to reveal to complete strangers.

I didn’t realise it at the time, but a Third Place had formed—pop-up style—right there under the clear night sky.

What do I think about adult friendships?

Adult friendships have to be intentional. They don’t have to be rushed, but there’s a strong preference for getting to the point. Dropping into quality, even vulnerable, conversation isn’t startling or rude—it’s refreshing and welcome.

Authentic relating circles.

What it seems we’ve done here is to give people the permission to be open and kind. To set it up such that people understand that talking to someone they don’t know isn’t just allowed—it’s the point. It’s Stranger Conversations, duh.

Here, you’re safe from quizzical looks, being ignored, and the pain of trying to make eye contact with a shifty target. No one wants to be on the receiving end of that.

After all, for the people who climb up the hill, get lost in Pearl’s Hill Terrace trying to find where on earth unit 02-38D is, and finally push open the nondescript door that looks like a storeroom entrance, striking up a conversation with a stranger is the easy part.

You’d think that there’d be many introverts in this community. And you’re right.

But not as right as you think—this isn’t hikikomori rehab.

Open hours at the Stranger Space.

People come to the Stranger Space for respite and inspiration: many extroverts also crave that. Perhaps they’ve been heads-down in a writing or coding project, or they’re seeking a calm energy around others they can’t find at home or in a cafe.

It’s a human thing.

The folks who make their way to this community have led many past lives—or they’re harbouring secret side projects that they don’t just anyhow share with others. Unwrapping these layers and going deep is typically an introvert’s superpower, making them insightful 1:1 conversation partners for anyone.

There’s a lovely balance here between mingling and focus that’s enabled by the diversity of folks that we attract.

A PowerPoint party of oddly specific topics.

It’s a key part of the Stranger Conversations experience that I delight in—uncovering people’s buried personas, the parts of themselves that they seem hesitant to talk about but actually really want someone who gets it to connect with.

So… what have I learnt from building this Third Place?

My relationship with Stranger Conversations has evolved through several ‘lives’.

At first, I saw running Stranger Conversations as action research: How does one live a more intentional life? Are there folks in Singapore who have gone off the beaten path, exploring possible versions of themselves, and have persisted? Could I also absorb some of that mojo, to give myself the courage to do likewise?

That’s me!

As the answer shifted from a tentatively delightful ‘maybe’ to finally a resounding ‘yes’, I realised that there was no turning back. The last residues of the past had dissolved: I didn’t need to look back any more, there was nothing I had left behind that I feared losing.

Then I viewed myself as an event curator: taking a backseat to create experiences for others. I was a host, someone who held space for the experience and the strangers to speak for themselves. People came. More followed. They thanked me for keeping this going. And they wanted to know why I was doing this.

A fishbowl conversation: an experiment in open meetings

What I’d done was to put my own journey of exploration out there for others to be a part of. Stranger Conversations had become my story, a living artefact through which people could feel my enthusiasm and see it reflected in themselves.

We think about exploration as going someplace and finding people to be inspired by.

I propose a reframe: exploration as drawing people into your journey and becoming inspired through the process and the mix.

That’s what I tell people now, every chance I get. In this latest iteration of my persona, I’m the nudger-in-chief.

Holding space with kopi (coffee).

Together with the community, we’ve only just come up with a working definition of a Third Place:

A commons where people can step away from their roles at work or home and generate collective good.

Even the simple act of relating deeply to strangers on picnic mats and taking something meaningful away from that experience qualifies as generating collective good. There’s more: rich conversations lead to fresh ideas, fresh ideas fuel movement, and with movement comes vitality, mixing and incidentally, fulfilment. But—yes— just showing up to a third place already gets you halfway there.

It’s really about you. And you, you, you, and all of you.

Can social life as grown-ups be more than just a running series of catch-ups with friends we’ve held on to from the past?

I believe adult friendships are ultimately project-based.

It’s a natural conclusion when you put the following ingredients together :

• Permission to be open and relate deeply

• Room to express personas that don’t fit at home or work

• Opportunities to generate collective good through personal actions

• Shared desire to get to the point

• Awareness that you’re figuring something out

And, having a space—a Third Place, it turns out—to greenhouse all of the above just seemed like a good idea.

From first-timer to host in a couple of weeks.

From doing just one thing at the start of this journey, Stranger Conversations has blossomed into a constellation of projects, as I work with each stranger to figure out how this community fits their current season of life.

And as things take shape, there’s an emergent vibe at the Stranger Space that I haven’t found anywhere else—I really enjoy it here.

It’s uplifting yet calm, and productive without pressure, and there are always stories from strangers to look forward to. It feels like a design studio where you’re always in dialogue with ideas in progress. It’s spacious like a playground—where there’s no need to perform; only to engage and to try.

Sometimes I wonder: Wouldn’t it be nice to set aside my role as a founder and community builder? To be a player in the scene of a Third Place like this?

That’s what I realised I was looking for all along.

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Support Jin Shaun and his team by giving them a follow at @strangerconvos on Instagram, and consider backing the Stranger Space at Pearl’s Hill Terrace by becoming a founding contributor.