The Importance of Talking to Strangers

The secret to sensational travel has little to do with seeing sights, finding the perfect hotel, or even choosing the right destination. It has everything to do with connecting with the people who call that place home. And the easiest way to do that is ridiculously simple—Talk to strangers.

Nearly twenty years ago I was on a chairlift in Idaho, enjoying the tail end of a glorious ski day. The friends I was staying with had gone home for the day and I decided to squeeze out a few more runs on my own. On the way up the lift I randomly engaged in conversation with the stranger beside me, a young Austrian guy who was working in Sun Valley for the season, schlepping luggage at a hotel and teaching snowboarding.

Curious to see how good an Austrian snowboard instructor might be, I suggested we take a run together. You’d have to hang out at Japanese steakhouse for a month to see someone carve with such speed and precision. Extraordinary. So we took another run. And another. The Austrian stranger has since become a good friend and visited our family so many times the kids affectionately know him as ‘Uncle Phil’.

There’s nothing exceptional about the story of Uncle Phil. Relationships born in a similarly serendipitous way are a dime a dozen. If you think about it, virtually everyone who’s close to you (apart from family) was once a stranger.

While we can (and should) practice talking to strangers wherever we are, the practice is especially powerful (and useful) when you’re on the road. Talking to strangers is like travelling with a skeleton key that opens the doors of the world. The only wrong way to do it is to not do it. It’s simple, just start talking to people. Ask them where to find a good coffee. Ask them for directions. Ask what they’re eating. Ask what they’re making. Ask what they’re painting. Anything. Just talk.

For sure, we’re all born with this intuitive skill. But I’d be remiss if I didn’t mention my greatest mentors in this area—Martha & George Butterfield. Along with Martha’s brother, Sidney, they created the truly pioneering travel company Butterfield & Robinson (aka B&R) in 1966, a staggering five and a half decades ago (Note: you can read all about B&R’s magnificent story in Slowing Down to See the World, a book I wrote a few years ago).

What I learned from George & Martha is the art of engaging in conversation with graceful zeal, generous kindness, and a sparky sense of playfulness. That’s Martha on a fishing boat, somewhere in Greece, many years ago. Who wouldn't want to be there? Who wouldn’t want to sip ouzo, break bread, and chit chat with these characters. That’s how you get to know a place. That’s how you travel.

So, next time you step off a plane, disembark a boat or bicycle, and find your feet somewhere new, you know what to do. Talk to strangers. The world is full of Uncle Phils and fishermen who are just waiting for you to strike up a conversation.