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The Weekly Challenge is a column that tackles self-improvement seven days at a time.

When we are young, the message is clear: Talking to strangers is bad. But what about when we get older and continue to follow the same behaviour patterns, not because acknowledging an unknown person is dangerous, but simply because that's the norm?

We wonder why we're constantly hearing about how isolated modern society is: Facebook is making us lonely, smartphones mean we never have to make small talk on the bus, and the prevailing assertion that the world is becoming more dangerous (though crime stats are declining) causes us to close ourselves off from random social connection. What's lost (besides the hours of non-refundable time devoted to Tweeting your life rather than living it) is that warm and fuzzy feeling that comes from being part of a community.

A recent study conducted out of Purdue University in Indiana shows that people feel a greater sense of social connection after experiencing even the most minor acknowledgment (smile or even just eye contact) from a stranger, and conversely feel ostracized when their presence goes unacknowledged. It got me wondering about what it might feel like to be an agent of social connection rather than someone who almost always looks down at the pavement while listening to an iPod. I vowed to say hello to every single person who crossed my path.

These are the people in my neighbourhood

As far as nations go, Canada is pretty darn chipper. In a 2012 Forbes study that ranked countries on the basis of friendliness, we came in fourth behind New Zealand, Australia and South Africa. As for my own home turf, however, I think those infamous beer ads that came out a few years back ("Coors Light: Cooler than most people from Toronto,") speak volumes, at least in terms of our reputation. I've never found the city to be particularly frosty, but maybe that's because I too am only slightly warmer than a chilled beer can.

I kicked off the experiment with a trip to the grocery store. My first target was about 15 metres away, walking toward me on the sidewalk. I'm not generally shy, but suddenly I began to panic, hearing the Jaws theme song in my head as she approached. I could feel my face getting hot, my heart rate going up, and then it was now or never. "Hello," I said with a friendly, Mr. Rogers-esque lilt. "Hi," she responded neutrally, not quite sure what to make of my unexpected gesture, but not totally freaked by it either.

Within 48 hours, I said either "hello," "hi," "nice day we're having," "what's your dog's name?" and "do the strawberries look good?" to 62 people and encountered pretty much every reaction you can imagine: confusion, discomfort, mild terror, total lack of acknowledgment (this happened a lot, including from strawberry lady) and enthusiastic hello back. In some cases, it felt as if my unexpected salutation gave people permission to do something they really wanted to do, but for whatever reason (social norms, not wanting to seem like a psycho etc.) felt they couldn't.

Bacon cookies and other amazing discoveries

To take the quest for communion a little further, I struck up several random conversations. I grew up with a dad who never met a clerk/waiter/person-in-an-elevator he couldn't chat with, so this wasn't totally unfamiliar territory. While my effort to discuss strawberries at the grocery store was dead in the water, another attempt resulted in a tip to try the bacon-and-caramel cookies. (I did. They were amazing).

By far my favourite interaction happened when I was walking through the park. I saw an elderly man sitting on the bench. Beside him was a second empty bench, which is obviously where I would have normally sat. Instead I plopped down next to him and leaned on that old small-talk standby. "Nice weather we're having," I began. He agreed and soon we were chatting about the neighbourhood. We talked about how much the area has changed, what's good about that, what's been lost. He told me that he bought his house for $17,000 and was recently offered more than a million. We talked about travelling, sharing our favourite cities that we'd been to and the ones we'd still like to visit.

It felt good to be someone who was putting a spring in other people's step; even better, by behaving like a sunny, open, friendly person, all of a sudden I was one. While I won't continue the extreme measures of my experiment (it's exhausting and I can't wait to get back to my book-on-tape), I will try to make eye contact and, every so often, to share a bench.

Reader responses

I talk to the people around me everyday. In line, in the elevator, on the street, at the dog park etc. The energy you put out there is exactly what you get back. There are a lot of wonderful people in this world. I for one am not willing to miss any I may pass by.

– Briar Main

You started with one of the hardest ones! Most people carry thorough childhood conditioning well into adulthood and avoid talking to strangers as a rule.

– Joe Macartney

Years ago, I made the committment to talk to strangers – much to the horror of my children. This has enriched my life in many ways. I feel part of a larger community chatting with the cashier, people in the gym, in the line at the market. And now the checkout girl at the grocery store knows me and I know her .... and the big city has become more like a small town.

– Karen Liddiard

NEXT CHALLENGE: Learn to take constructive criticism. Meet up with key people in your private and professional life and ask what you could do better. And attempt to be open and responsive to their comments. Sign up at to tell us how it went.

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