Talking to strangers
Taking Malcolm's approach.
This week, I’ve been spiralling down a rabbit hole of Martha Stewart interviews on YouTube. Yes, I saw the new Netflix documentary, and just when I thought I’d seen every possible side of Martha, there I was, watching her discuss life lessons she’d picked up from her friendships.
The real surprise for most people has been her friendship with Snoop Dogg. Somehow, the domestic doyenne and hip-hop icon forged an unlikely bond, which continues to capture the hearts of many.
As Martha explained in one interview, knowing someone from a different world made her more mindful, serving as a reminder that connection can be far more layered when it comes from unexpected places.
I’m paraphrasing, of course. But my mind immediately went to Talking to Strangers, Malcolm Gladwell’s book, which dissects the nuances of interacting with people outside our usual circles.
Gladwell wasn’t writing a guidebook for travel, but his exploration of human connection resonates with anyone who’s ever set foot in a new city and wondered about the lives around them.
Learning about others doesn’t exactly guarantee world peace. Not at all. But it certainly adds ‘texture’ to our understanding of people.
He makes the case for talking to strangers as a way of truly seeing them—simple in theory. We can be so quick to make judgments, relying on limited information to form opinions that are more comfortable than accurate. Perhaps it’s our instinct for self-protection, but it leads to a habit of seeing only what’s convenient or affirming.
The irony is, when we travel, we’re surrounded by people who are, by definition, unknown to us. And even then, we might slip into the same bubble we inhabit at home, observing from a distance rather than engaging in a more hands-on way.
But imagine what we could gain if we opened ourselves up just a tad more. The idea isn’t that every stranger will become a friend, but even small exchanges can broaden our perspective.
This isn’t new news.
I’ll admit, I’m not the type to strike up conversations easily (I’ve become so awkward since the pandemic). However, I’ve noticed that travel gives me a kind of permission slip. Whenever I’m in a new city, or especially when I’ve just moved somewhere, I find myself more open and willing to engage with just about anyone.
Gladwell writes about the value of these interactions—they’re meaningful not because of their depth but because of their authenticity. I think back to all the random conversations I’ve had. They can be entirely fleeting, but unforgettable in their own way.
Whether you’re introverted or extroverted, the heart of these encounters lies in being open to them and acknowledging that even the briefest exchange might lead to something unexpected. It’s really more about curiosity than confidence.
This is exactly what makes travel such fertile ground for talking to strangers. As visitors, we’re already positioned as observers, approaching everything with a greater sense of wonder. After all, we’re there to experience something new. So we might as well extend that openness to the people we meet along the way.
It’s a habit worth cultivating, so long as you’re not annoying about it. The world can feel so isolating these days, and these spontaneous conversations can remind us of our shared humanity.
To avoid being that tourist, keep it simple. Compliment someone’s meal choice or ask them for a recommendation. Most people are happy to share their favourite spots or tips, especially if your approach feels genuine and respectful. Timing, therefore, matters—never catch someone in a rush.
Not every exchange is bound to be groundbreaking or life-changing, nor do they have to be. But some could surprise you.
love this piece.