Small Talk Isn't the Problem - It's You

have a conversation with anyone, anywhere, anytime

May 21, 2025

The cool thing about traveling is that it will certainly put you in uncertain and oftentimes uncomfortable situations. Those are the best.

You’re not just traveling for the sake of traveling. You’re out to find connection.

So, how do you to get people to talk to you?

First, make sure that you’re approachable.

Get off your fucking phone.
Uncross your arms.
Make eye contact.
Lean forward.
Be open.
Smile.

Now what?

Easy.

Talk to someone first.

I guarantee you, everyone who is sitting in a communal space by themselves wants to be engaged in conversation.

People are bottomless stories just waiting to be told.

But they - like, you - probably don’t know that we’re all out here playing an infinite game of chicken to see who is going to make the first move.

It’s you. You go first.

How to Talk to Anyone, Anywhere, Anytime

There are no clear-cut rules of engagement but generally this phased-approach has been pretty foolproof for me.

Let’s scenario-play a bit and use the example of me on a road trip rolling up to La Reina bar at the El Rey in Santa Fe last week.

PHASE 1

Sussing out if the other person is up for a convo.

Step 1: Start with a question related to the setting you’re in.

We’re at a bar. Engage the person next to you with a softball question: What’d you go for? (you can point to their drink to make it super obvious).

Step 2: Here’s the best bit: actually listen to their answer.

Step 3: Bring forth a follow-up question. Interesting! What drew you to that on the menu?

Based on how that answer goes, you’ll know pretty quickly if you/they want to continue talking.

They might say something like “it sounded good” or “I always get a margarita.” That’s a conversation ender. Move on. They aren’t up for it.

But if they say something like “I was intrigued by the combination of Génépy and Mezcal,” wooo baby, you’re in business!

Step 4: Offer a subtle initial compliment.

For instance, if you have no idea what they just said, you can say as much “I love that you know what you like.”

Or you can say, “wow, that sounds delicious - you’ve got great taste. I’m going to try that.” You’re basically making them feel like they gave you a recommendation. Because you did ask! So now take the recommendation.

As you wait for your drink order, move to the next phase.

PHASE 2

Becoming familiar.

Step 1: Introduce yourself.

Step 2: Ask for their name. Exchange pleasantries.

Step 3: Ask another question. So, what brings you here?

Step 4: And another question related to their answer. What are you most looking forward to doing/seeing on your trip?

Steps 5-117: Listen. Ask more questions. Follow-ups. Tangental. Probing. Clarifying. Extrapolating. All the questions.

Generally speaking, “what” questions are usually easier for other people to answer and provide fruitful ground for rich responses.

And “how” questions add more details for you to latch on to so that you can - you guessed it! - ask more questions.

PHASE 3

Exiting the conversation.

This is probably the hardest thing for most of us. We’ve spent time together. We get attached. We’ve got this whole loss-aversion thing.

But we don’t need this interaction to be anything other than it is: people surprising, delighting and learning from each other.

You do not have to exchange phone numbers and promise to keep in touch. This isn’t camp. (You never actually wrote those letters to bunkmate Becky and probs haven’t thought of her in 22 years).

Identify a natural break in the convo. Stop asking questions. Simply say it was nice to meet them. Wish them well. And bonus points if you bring back a specific thing from earlier in the convo.

No matter where you are or where you’re going, we’re all just identical strangers.

Yesterday I read something from the The Hotel Crush Diaries about the concept of sonder, which by definition is “the realization that each random passerby is living a life as vivid and complex as your own.”

Other people are the main characters in their lives. And we can all be extras!

New Goal: BE AN EXTRA AS MUCH AS POSSIBLE!!!

All you gotta do? Start a conversation.

And to talk to anyone, anywhere, anytime? Be more interested than interesting.

Be curious about other people. Their experiences. Their stories. Make them feel seen and heard and acknowledged.

Show up for a moment in the background as people live the movies of their lives. Yours will be extra rich for it.

When’s the last time a stranger made a lasting impression on you?