How To Talk To Strangers

Talking to people who I know is hard enough. But ask me to talk to strangers? Well, I’d rather be doing calculus problems. 

Imagine, though, that I don’t have a choice. Imagine a world where I cannot choose calculus over conversation. Then, I focus on asking good questions and follow ups, which takes some of the pressure off of having to say something interesting. I should note, though, that I listen with genuine interest and ask for more information because I want to learn more.

Because talking to strangers is inescapable, it’s usually top-of-mind. Lately, it seems to be top-of-mind for others as well. I’ve come across several “conversation strategies” articles in the past few months that have just been sitting in open browser tabs. I decided that I had to do something with them. So, here are a few of my new favorite ideas.

A growing chorus of conversationalists are trying to kill off the classic “so, what do you do?” but sometimes, you can’t avoid it. When it comes up, I’ve had some success with this tip from Austin Kleon (who stole it from Paul Ford). Here’s Paul Ford:

“Just ask the other person what they do, and right after they tell you, say: “Wow. That sounds hard.” Because nearly everyone in the world believes their job to be difficult.”

This can get people to open up a bit more about the specifics of what they do and some of the challenges.

Next, game designer Jamey Stegmaier recommends that you come prepared:

9. Always enter social situations with an answer to “What have you been up to lately?” Also, instead of asking that question, help the person with more constraints (e.g., “What did you do this past weekend?” or even more specific: “Did you try out any new restaurants this past weekend?”)

It sounds silly now, but before reading Jamey’s article, I had never considered having an answer for this question at the ready. It always comes up, especially with a) my mother and b) mid-level friends who I haven’t seen in a few months. I think it helps to remember that while you have intimate knowledge of your own life such that very little seems interesting (unless you just got back from a big trip or changed jobs), the other person will usually be happy to learn something you consider small, like that you just went to your favorite restaurant, saw a new movie, or completed a project at work.

Finally,  blogger Lama Al Rajih (via Tyler Cowen), has posted a long list of interesting questions to try. Some of them seem like bummers and I’d be hesitant to bring up topics like regret or loss with people I don’t know, but I am looking forward to trying the more neutral-to-positive ones like:

-What simple thing still blows your mind?

-What taste do you have that most people don’t have, where does it come from, and how has it helped you?

-What is the most significant thing you’ve changed your mind on in the last year? Why did you change your mind about it?

-Which question can you ask to find out the most about a person?

-What color best describes your personality?

But my favorite is:

“There are two types of people in this world. What are the two types?”

The first thing that comes to my mind is “young” and “old.” Not in years but in spirit. 


Each Monday, I share strategies to help you pursue your passions. Try it. You’ll like it.

Photo by HIVAN ARVIZU @soyhivan on Unsplash

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