I am not a social person and do not especially enjoy social events. For years in college, I would repeatedly say the wrong thing to people, horribly offending them with no idea how or why it had happened. My friends would then laugh and remark how I’d “done it again.”

But I have cobbled together one simple strategy that my fellow weirdos may find helpful.

How to Talk to a Stranger

Ask questions. Then ask more questions. Then keep asking questions.

“Oh, you work at X? What’s that like? Uh huh. So what companies do you represent? Oh really. What are they like? Oh really? What type of software do you use for that? How did you get that job? Oh you used to work at Y? What was that like? What’s the craziest Z you’ve seen?”

This sounds stupid. In fact, it’s basically the way computer chatbots operate.

But it is remarkably effective. And it’s not as creepy as it sounds. I’ve found that by asking many questions, I can eventually land on a topic that genuinely interests me and have a real conversation.

Here’s why it works. Everyone you meet is an expert in something. It may be something seemingly trivial, like mall security procedures¹ or class action lawsuits, but no one’s made it 20+ years in life without learning a lot about something.

If you can find that hidden expertise, you’ll be amazed at the level of detail and character you can get out of someone about their job, their life, or their hobbies.