Talking to Strangers: A Guide

I often talk to strangers, and have gotten near-universally positive results from doing so. I've often been asked how I do it. Here it is: A guide for people who want to talk to strangers, but don't know how.

Why do it 

Before you learn how to do it, you have to really want to do it. If you're feeling inspired, you will find a way on your own.

1.) Everyone around you knows countless things you don't. They know things about Renaissance art, Brazilian culture, microbiology, transatlantic shipping, marketing strategy, food preparation, car repair, horticultural technique, hair styling, raising children... you get the point. Everyone around you is profoundly fascinating.

I'm of the opinion that anything is interesting if you learn enough about it, so to leave this incredible wellspring of information untapped seems at the very least a waste. But even if you don't feel the same natural curiosity, it's still interesting to ask why they're interested in these things you feel nothing for. What's there that's so captivating?

2.) Everyone around you contains amazing stories: stories to inspire you, to infuriate you, to make you weep, or laugh, or look at the world differently. These stories can be life-changing (they certainly have been for me), and they're all roiling there, just beneath the surface. You just have to pull them out.

3.) People can be of great help to you. I once bought someone some food. That same week, my car broke down, he happened to be passing by, and helped me fix it. While he was doing that, he casually dropped some great wisdom I try to live by to this day. These kinds of experiences are fully within your grasp. Great collaboration breeds great collaboration. Great joy breeds great joy.

Who to choose

Don't talk to people who have stuff in their ears, who are clearly in a rush, or who don't reciprocate. (This eliminates a lot of people, but it doesn't eliminate everyone. And there are some exceptions to these rules, too.) Give people a little something, and if they respond positively, give them a little more. This is how you start to build connection. If they don't give anything back, smile, shrug, move on with your day, and assume they, much like you, are an incredibly busy person whose life is packed with a diverse array of interesting hobbies and meaningful relationships.

A lot of people who want to talk to strangers but don't are afraid of bothering people. Fair enough, I've probably bothered some people. But subjecting someone to 5-10 seconds of annoyance or discomfort is beyond worth it when you consider the massive reward of genuine connection. I get the former far, far less often than I get the latter, and as I keep improving, the ratio is skewing in my favor even more. As it turns out, you and I offer just as much knowledge, story, novelty, and value as the people we're going to talk to.

Approach: 3 methods

1.) Comment on something in the local surroundings: "I love your hair", "That is so beautiful", "Wow, they painted the trains, that's cool", "I wonder how they do that?", "Dang, that's big". I once said the last one to a guy on a dock while pointing at a ship, and he proceeded to teach me all about Atlantic shipping, showed me a ship-tracking app where you can see the ocean lit up like a constellation, and recommended a great restaurant to eat brunch at. Environmental observation = instant connection.

2.) Get people to approach you. Find a skill that's visually or aurally attention-catching, practice it, and fall in love in it. Get so invested in getting good at it that you want to practice it even when other people are watching. For me, the former was card tricks, shadow puppets, practicing ASL, or dancing (even a slight rhythmic twist of the shoulders and a smile is enough to spark something); the latter was beatboxing, clapping fast, or bodily percussion. People voluntarily coming up to you is the easiest way to start a conversation.

3.) Smile, wave, say "Excuse me,", then ask a question. "Can I get your opinion on something real quick?" "Where did you get that watch?" "Do you need help? You look lost." "Do you know where the park is?" and so on. Note: this option does requires good conversational skills to maintain. I recommend pairing with #1. 

Good conversational skills

Give a little, ask for a little, then give a little more. Do your best to give just a little more than what you get. This is the basic method to building good conversations.

To give, ask yourself: What does what they said remind you of? What can you respond with that might interest them? How can you provide additional meaning or context to their existing knowledge? What stories have you lived that resonate with theirs? What's something funny about the situation?

To ask for more, ask yourself: What's interesting about this person's story? How does it relate to something you don't know much about? How can you get more of their knowledge? Where does it come from?

Failure

A lot of people think I'm confident at this because I succeed a lot. The truth is the opposite: I'm so confident because I've failed a lot. Confidence comes from continuing to practice something even though you fail, because that's actually how you get good at things. Reframe failure: either you're succeeding, or you're learning. Those are the only 2 possibilities.