I’m sitting in a café—Little Ruby’s, tucked away in the heart of SoHo, New York. Outside it’s, for use of a less confrontational word, a crisp -10°C. This is the kind of cold that jabs its way right into the places that any man would find it hard to admit, but a cold you have to accept begrudgingly as you walk down the exposed streets.
Inside, though, the hum of conversation and the scream of the espresso machine create a small escape. My second flat white is currently being masterfully crafted by the resident Melbourne barista, and as I sit here waiting for my avocado toast, I felt like writing about a story from my early 20s.
To preface this story, I should say that we’re going to center this blog around the concept of generational differences, cultural norms, and the art of meeting strangers.
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Last night, after returning home from a performance of Aida, I was marveling to a friend that these days I always seem to meet new people when I’m out and about.
Take last night, for example. My neighbor in the audience was a retired doctor in their early 70s. A fervent supporter of the arts ever since their first visit to NYC at 16, they told me about their upbringing in Montreal, growing up as the middle child of a family of 13. At Christmas that year, they spontaneously traveled south to the Big Apple, defying all family expectations, only to return home and start planning how to move there for good.
The story then unraveled further, painting a picture of their life: studying medicine, living in New York during the 1970s, and becoming a private art collector, opera aficionado, and patron of the arts. Icon after icon fell from their mouth as they recalled operatic legends: Schwarzkopf, Callas, Sutherland, Pavarotti, and more. Every name felt like a thread in the tapestry of their life.
At the end of the performance, contact details were exchanged, applause was given, and we parted ways. But what stayed with me wasn’t just their stories—it was the effortless serendipity of the connection.
Now, in my 30s, I’ve found myself far more open to these kinds of moments. I’ve been chasing what I like to call a “vibrant life”—a commitment to curiosity, spontaneity, and connection. But when I think back to my 20s, I was a very different traveler.
A Tale of Two Operas
A few nights earlier, also at the opera, I had a very different experience. This time, I was sitting next to two people around my age, both attending solo. We were watching La Bohème, a story filled with raw emotion and passion. Yet during the two intervals, none of us spoke.
Nobody dared to chat. Myself included.
Instead, we all turned to our phones—Instagram, Facebook, texts from friends, mindless games—filling the silence as if it were a void to be avoided. The room felt like “conversation closed for business.”
This stark contrast made me wonder: Why does my generation seem so disconnected from each other?
The Small City Mindset
I grew up in Invercargill, a small city at the southernmost tip of New Zealand’s South Island. For those unfamiliar (and, for Southlanders reading this, let me confirm: on my travels, I’ve met more people who have been to Gore than Invercargill), it’s a place defined by vast green landscapes, biting horizontal rain, and the kind of familiarity that comes with a population of 50,000.
It’s the sort of place where you know your neighbors, recognize faces at the supermarket, and grow up with a comforting sense of community. But there’s also a quiet insularity—a subconscious preference for the familiar over the unfamiliar.
When I started traveling in my early 20s, I unknowingly carried that small-city mindset with me. At 22, a good friend and I embarked on a whirlwind journey through Australia, Hong Kong, Sri Lanka, Qatar, and Italy. It was ambitious and chaotic, full of trains, buses, Airbnbs, and bucket-list destinations.
But looking back, one thing stands out: I didn’t make a single lasting connection with anyone new.
Not one.
Despite being surrounded by opportunities for connection, I clung to habits that felt safe—talking to my friend, sticking to the itinerary, and relying on my phone or guidebook to fill the gaps.
I was so focused on doing travel that I forgot the essence of it: to connect, to notice, to be open to the unexpected.
The Art of Being Present
Fast forward to now, sitting in this SoHo café, I realize how much has changed. These days, I strike up conversations with strangers at concerts or markets, eager to hear their stories. I’ve learned that the richness of travel—and life—isn’t just about the destinations. It’s about the people you meet along the way.
But why does it feel like these moments of connection are harder for my generation? Is it our phones, drawing us into the comfort of the already known? Or is it a fear of vulnerability—the risk that reaching out might be met with rejection?
A Generational Lens
When I think back to my opera neighbor, I wonder: Is this openness a generational trait? Older generations grew up without the distractions of smartphones and with a different social framework—one that placed a higher value on in-person interactions.
In contrast, our generation often leans on curated digital connections, sometimes at the expense of the real world. It’s not a judgment, but an observation of how technology and cultural shifts have subtly reshaped how we engage with others.
My Call to Arms
So, here’s my challenge: Let’s become a generation that breaks the silence.
Put down your phone. Strike up the conversation with the stranger next to you. Say yes to the unfamiliar.
Whether you’re in a café, a bookshop, a lunch queue, or an opera house in a foreign city, there’s a whole world of stories waiting to be told and heard. You just have to be willing to listen.
Because in the end, life is about connection—and the most vibrant lives are the ones open to serendipity.
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