How to increase your chances for illuminating impromptu exchanges

Last week I wrote about your desk neighbour’s inspiring stories. This week, I ventured even further.

During the pandemic, one of my favourite past-times was overhearing conversations of strangers who sat on the benches on Parliament Hill, staring out across the city. Being in earshot for just a few moments as I passed, a window into a parallel universe - a wholly different microcosm - would open up to me. Perhaps it is a form of escapism. Maybe it is just an alternative, more absorbing form of entertainment, like reading a collection of essays by different authors. But I started to look forward to it as part of my walks. What would I learn about today?

You’d be forgiven to assume that all anyone would be talking about was the pandemic. Sure, there was a lot of that. But there were also conversations about DIY tea-leaf skin treatments, various friendship dramas, the questions posed to oneself when being a spiritual standup comedian, and reality checks on whether that friend’s life who travels around the country to put up festival stages really is that enviable. On my way home, I’d ponder the same questions in my head and sometimes, once home, google some of the topics that were more unfamiliar to me. 

Nowadays, as people around here are no longer terrified of relative proximity to strangers, it is easier to become part of the conversation. You could go further and say that many of us are now desperate for human contact after two years of relative isolation. I wouldn’t describe myself as an introvert or an extrovert (in fact, the MBTI personality type indicator placed me firmly in the middle, if you believe in that kind of thing), so while striking up conversations with complete strangers doesn’t come naturally to me, I get enormous enjoyment from it when it does happen. 

Last Saturday, as I walked up the hill once more, my two-month-old strapped to my chest, I noticed another baby-lugging dad coming down my way. Holding up a book in his right, it looked as though he was reading to his daughter. Adorable. I asked to take a snap, and we ended up chatting about the book he was reading - to himself, it turned out - and his friend who had penned it. Later that day, my wife and I passed a man who looked like a time-traveller from 1980s New York City, complete with the all-leather outfit, long curly hair, and an analogue full-format photo camera. Sure enough, we got curious about his story.

Structured and solution-oriented, as you know I am, I contemplated how to increase my chances for a chat with a stranger. I was reminded of the TIARA framework introduced in The Two Hour Job Search - which also recommends its application in social contexts. There’s a strange feeling to coming up with and applying frameworks for social interactions, which are generally thought of as spontaneous. But if you don’t have the extrovert’s instinct, why not train your muscle memory for more mutually enjoyable interactions? 

Suppose you were curious about a simple guide. In that case, you could try complimenting passers-by on a standout accessory and ask a question about it. Smile, keep some distance, ask before taking pictures, and keep it short - people are on their way somewhere after all. Then again, much of the magic actually comes from the spontaneity of getting talking to strangers. Even in a problem-solution focused mind, some things are better left to chance.

This story was originally published as part of the newsletter Seven Things.