Talking to Strangers

Hello, fellow thinker!

This week, I met two total strangers, and it reminded me how great it is to meet new people. Not in a “networking” situation, but in normal day-to-day life. I had the pleasure of that happening twice this week and it was energizing for a socialite like me.

Please enjoy my letter on talking to strangers!

The first moment happened when I was catching up with a friend over coffee and dessert in one of those busy New York cafés where you can barely hear yourself think. A woman was sitting near us, and out of nowhere my friend leaned over and asked, “Excuse me, can I see the video you just took with your camera?”

That tiny question turned into a whole conversation. She was a tourist from Los Angeles. She was an art director who’d worked with Netflix and EA, just in town for a week. Within minutes, we were talking about her work, creativity, and life in L.A. It was a reminder that interesting people are everywhere; sometimes all it takes is one curious question to find them.

A few days later, I had another moment like that while taking my kids to their acting class. It was the final showcase weekend, so the lounge was packed with parents waiting for the performances to begin. But the room was silent, and everyone was buried in their phones. I couldn’t help but notice it (so sad to see it sometimes). I even took a photo and used AI to replace everyone’s phones with bananas. Because honestly, that’s what it looked like.

Next to me sat a woman doing a crossword puzzle. Before I said hello, I went through a full mental debate about how to start the conversation. Part of me wanted to sound casual, and part of me wanted to say something completely ridiculous just to amuse myself.

Here were some of the weird lines that flashed through my head before I thankfully chose the normal one:

• “Wow, you look lonely. Want to chat?”

• “I’m practicing talking to strangers this week — consider yourself my first victim.”

• “I bet you don’t know any good spots — I’ve lived here forever.”

• “You seem like someone who wouldn’t report me if I said hi.”

However, what actually came out of my mouth was:

 “Hey, do you have kids here? Or…?” (facepalm)

Without missing a beat, she looked up and said completely straight-faced,

 “No… I’m just here hanging out. I have no kids.”

It was hilarious. That one line broke the ice completely, and from there, the conversation just flowed. We talked about our kids, hobbies, and the endless cycle of trying new activities. Then she casually mentioned, “When I was on Jeopardy...”

That stopped me in my tracks. She’d actually been on Jeopardy and was now applying to be on Wheel of Fortune. I thought that was incredible how many people quietly have these vibrant, interesting stories right next to us, hidden behind their screens.

I left that day thinking about how talking to strangers is like discovery of new people. It’s a way to reconnect with the real world, to find inspiration in the people around us, and to remember that everyone has something remarkable going on.

Sometimes fulfillment doesn’t always come from chasing big goals. Sometimes, it starts with looking up and saying hello.

When was the last time you talked to a stranger?

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Keep thinking, my friends!

⚠️ First Time reading? Catch up on all my letters here: https://soberthinker.beehiiv.com/