I:
The most important people in my life all have one thing in common: at some point early on, we had a conversation that refused to end.
A great conversation.
We’d talk for longer than we should have and in those moments, I knew they’d stay in my life:
In my first year, I met someone at a study session. We never opened our notes. We instead talked for twelve hours.
In my second year, I stopped by a friend’s place at 9 p.m. We talked until sunrise.
In Japan, I met a fellow solo traveler. We planned to visit temples together one afternoon. We just kept talking and spent a month traveling together.
These moments are rare; but when they happen, I always notice (it’s hard not to). These conversations are a tell. And a very good one.
II: Something happens at hour three
Everyone can seem interesting at the start; not because they necessarily are, but because there is a lot of lore to exhaust.
A great conversationalist isn’t compelling because they’re holding some secret reservoir of fascinating stories waiting to be unlocked.
They notice subtle details, ask unusual questions, and frame even simple topics in ways that make you think, laugh, or feel something. This can make even mundane things feel worthwhile.
It’s the lens, not the inventory. No matter how many good stories you have, you must eventually run out.
If the goal is finding someone I can talk to forever, I want to burn through the highlights quickly. That happens about three hours in. And what begins then is the real conversation.
This isn’t just about meeting someone new. People only collect stories so fast; if their pace of telling stories outpaces their pace of living them, the well runs dry.
In fact, the well will assuredly run dry, unless you can talk about more than just events. Even particularly gumptious people can only do so much; and so if their conversational fuel comes only from what’s happened to them, silence is inevitable.
Great conversations transcend things.
They get to topics.
III: Topics and things
In Ecuador, I visited the Amazon, went horseback riding, hiked a volcano, and yet, one of my favorite days was a "boring" day when all I did was travel 14 hours straight on a riverboat & a bus from a lodge back to Quito.
There was objectively nothing to talk about.
We quickly exhausted our inventory of things. So we started talking about other things. Not necessarily about what had happened, but how we made sense of it.
This is the difference between things and topics.
Things are concrete. What happened, when, and to whom. You get a finite supply of them.
Topics are abstractions; ideas. They arise from things, but then transcend them. They’re not just about what happened. They’re about what it means, and what else could have happened, and how it makes you feel.
That bus ride could’ve been tedious; instead, it’s one of my favorite memories from the trip.
To specify, topics without things is not the end goal. In fact, topics need things to ground them in reality. Storytelling was the first educational medium for a reason; topics exist in things.
“Things” aren’t lesser. They’re how conversations begin. They give us shared context, updates, and memories. But they’re finite. Some friendships live entirely at that level. We meet up, swap stories, and the conversation ends when the list runs out.
These conversations appear more “productive” whereas great conversations about topics look like they meander or are an inefficient use of time.
Structured conversations feel productive because since things are finite, they can be fully exhausted. As a result, they tend to follow a predictable script that checks the open items off the list: life updates, new gossip, and shared memories.
By contrast, meandering conversations lack a clear purpose. This can feel aimless or indulgent.
But that inefficiency is precisely what makes them valuable. Without an agenda, there's room for surprise. You say things you didn’t plan to say. You discover what you think mid-sentence. These conversations end up generating information rather than just exchanging it.
The ability to talk about topics is a proxy for something else: philosophical compatibility. That is, shared curiosity about how to live; not just shared memories of what happened.
That kind of compatibility, the ability to dance around a topic and tease out meaning, is intellectual, social, and emotional. It feels like flirting.
IV: The subtle dance
Flirtation is a strange game. You’re revealing something, but just barely. A glance, a joke, a pause that lasts one beat too long. You’re signaling interest, but keeping just enough ambiguity to deny it, if you need to. If they catch the signal and send one back, you keep going. If they don’t, you let the moment dissolve and pretend it never happened.
Getting to a great conversation mirrors that subtle dance.
I’m tossing out small signals: incisive comments, unexpected questions; hoping one of them lands.
Just as topics and things need one another, small-talk and big-talk form a similar co-dependent relationship. The balance is delicate. Great conversations can be emotional and hilarious. Great conversations are actually like flirtation because they rely on a mutual vulnerability disguised as play.
The rhythm follows a shape:
The conversation progresses, I guide as much I let guide, equal pressure from both sides. I lean on my wit to make jokes and break any latent awkwardness quickly, comfort is important. There’s no silence; I’m “reaching” for the types of things I know they have placed on their bookshelves. I ask questions, but not too many, I don’t want to interrogate. I’ll tell stories when warranted, but as I do, I lower the armor each time. The story comes with a side of “why” and I pay attention to their reaction. I want to see recognition in their eyes. Now is my turn, I ask a question deeper than I should; sometimes in a jovial manner, but serious enough that they have the option to respond in earnest. Now we have gotten somewhere.
My friends have pointed out how often I ask “how would you describe your indescribable quality?”
It’s a perfect example of a deeper question I ask in a jovial manner.
The paradoxical nature makes it seem silly, but it’s strangely inviting. Some refuse to respond, some ask me to go first, and others take it in earnest.
Great conversationalists don’t all respond the same way. But at some point, a real conversation demands genuine sharing and earnest answers.
So maybe you’re not necessarily super comfortable with each other because you’ve just met, but there is this feeling that I understand you and you understand me. And as long as this mutual belief exists during the course of a conversation, genuine sharing ensues, and voila, a friendship begins to form.
V: Little surprises
Not long after I arrived in New York, a friend introduced me to one of his college friends. The three of us grabbed noodles in Chinatown.
My friend was quiet as he watched the two of us go back and forth, quickly we fell into discussing deeper topics while surfacing for air in moments of irony. Undoubtedly, we were having a great conversation.
Core to that were little moments of surprises; unexpected honesty that made us tilt our heads and say, “Wait, what do you mean by that?”
Some people look for people with common interests: someone who is also a “gymrat”, or has the same taste in music. I think this is quite wrong. Interests give you things to discuss, but people who can surprise you and find interestingness anywhere are permanently sources for great conversations; and in that cohort of people I’m certain you can find someone who hip thrusts two plates or likes Morgan Wallen.
Speaking openly, I’m afraid of becoming bored of the people in my life. I try to solve that by finding the type of people that renew my attention.
Boredom in relationships doesn’t come from familiarity, but from a lack of new experiences. You can have the same conversation ten times and feel differently about it each time, if you or the other person has changed.
Surprise matters. Not just for novelty, but as a test of aliveness. Surprise reveals who’s still asking new questions and growing.
VI: Great conversations
Someone quickly became one of my best friends.
I described them to one of my other friends as skillfully happy. It wasn't a phrase I had thought too much about, but it just came out. They had a way of being joyful that was more than just accidentally feeling good—they actively cultivated it.
When we first met, I remember feeling as if they had cheated off my test, they were talking about precisely the things that I enjoyed talking about. This could only last so long.
One evening, over a platter of oysters, we ran out of things and got to topics. They were not just skillfully happy, they were skillfully navigating a conversation about seemingly nothing at all and making it interesting.
It turns out, nothing can still be full of little surprises. And in the future nothingness of all the conversations you’ll have, the types of people who surprise you with how often they surprise you are the great conversationalists.
Great conversations:
Burn through highlights to get to what matters.
Aren’t efficient: they meander, surprise, and unfold.
Aren’t just about shared interests or shared moments.
Rely on mutual curiosity and the willingness to play.
Spark new ideas rather than just exchange information.
Reveal who someone is and who you might become around them.
These qualities show what really matters in the people we keep. At least for me, it's not their stories or charm but how they challenge your thinking and curiosity.
The people who keep showing up in those conversations make you think harder and notice more.
And when you find yourself in a conversation that stretches into the morning, you feel its rarity — and want to hold onto it.
That’s what a great conversation does. It makes you stay.
And come back.