I have become obsessed, although hopefully not in the clinical sense, with 43Things.com, a website where people reveal 43 goals they want to achieve, then find others with the same dreams and spur each other on. It's a mesmerising glimpse into the world's collective yearnings, which turn out to encompass everything from the overarchingly ambitious ("have a completely different life by this time next year") to the poignant ("stop hating myself") and the mundane ("return my overdue library books"). Others on the front page included "get laid", "go to Antarctica" and "destroy Christianity", though I think it might be problematic to attempt all three at once. Then there was the one that kept catching my eye: more than 300 people had decided that one crucial way to improve their lives would be to start talking to strangers.

This was why I found myself on a street in my home town of York the other day, trying to start conversations. The role models here are Liz Barry and Bill Wetzel, two New Yorkers who founded the Talk To Me project (nyctalktome.com), in which they held up signs at city bus stops, inviting passers-by to stop and chat. Obviously, I wasn't going to hold up a sign - don't be ridiculous - but their general tips on talking to strangers proved worth reading. They include: make eye contact first, don't have an agenda, ask lots of questions, and bail quickly if someone really doesn't want to talk.

Handily, and unusually, a police helicopter was hovering low over the city centre, allowing me to sidle up to various bystanders and unleash the following sparkling bon mot: "I wonder what that's all about?" I suddenly remembered Albert Ellis, the psychotherapist who'd urged me to shout the names of stations on the subway. The crucial thing was to stop caring if other people think you're an idiot.

Three observations: one, this is weirdly terrifying to do when you focus on it. Two, it makes you feel as if you're doing something incredibly shifty, like recruiting people to a cult. And three: if you do it a few times, the terror evaporates, and you'll suddenly find yourself in a group of four complete strangers, happily discussing recent violent crimes, the overcast weather, the performance of York City FC, and the history of English church architecture. I left feeling immensely cheered.

There may be some cultural variations here in terms of how revealing people are willing to get. I ran the experiment on a train in New England and got talking to a shaven-headed young woman who said she'd just been released after five days in jail for possessing a gun. She no longer had a gun, but hinted that she might have a way of rectifying that situation. We spoke for 40 minutes before I freaked out and went and hid in the buffet carriage. That's the wonderful thing about talking to strangers: you get to meet such an interesting variety of armed robbers.

oliver.burkeman@theguardian.com