For most of my twenties, I had a quiet but persistent belief about myself: I was bad at talking to people.
Not clinically shy, not visibly awkward – just off in the conversational department. I’d avoid parties early, dread small talk at work events, and feel a special letdown every time someone asked what I’d been up to lately. I would give a straight answer, they would give a straight answer, and we would both look around for him to save us.
I chalked it up to introversion. Then I attributed it to social anxiety. Then, briefly and anxiously, I thought I was just bored.
It took a casual conversation with a near stranger on a delayed flight to show me that the diagnosis was completely wrong.
We stayed at the door for three hours. He was reading a book on economic history; I asked about it. Within twenty minutes, we started a conversation about how the stories we tell about money shape the way societies break down. We talked the whole flight. By the time we landed, I felt more energized than most parties I’d attended that year.
I didn’t get his number. I hardly remember his name. But I remember the feeling, and more importantly, the thought that struck me in the midwest: I’m not bad at conversation. I’m bad at conversations that have nowhere to go.
The difference sounds subtle. It is not.
The “good conversationalist” myth
We tend to think of social skills as a fixed trait—either you have it or you don’t. The person who lights up the room is fair so. A struggling person is wired differently. We view conversational ease as a kind of personality trait: something that happens to you, not something shaped by circumstances.
But this framework misses something important. The quality of a conversation is not just a function of the people in the conversation. This is also a function structure please talk about
Some conversational formats are inherently generative. They invite interpretation, speculation, disagreement, and wonder. Others are essentially closed. These are not conversations at all – they are social events dressed up as conversations.
“How was your weekend?” not a question. It’s a handshake. “What was the best part of your weekend?” is a question. It opens something and closes something.
For years I faithfully performed the handshake questions and wondered why I didn’t feel anything afterwards.
What does “going nowhere” actually mean?
Not all small talk is bad. Some are actually useful—a way to signal safety, to generate warmth, to grease the social gears before they get to the real thing. I don’t want to be the person who corners a co-worker at the coffee machine and asks about their current relationship with death.
But there’s a difference between small talk like a ramp and small talk like a whole road. A lot of the social conversations I was afraid of weren’t just light — they were self-sealing. Every question had a socially approved answer, every topic had an invisible ceiling, and everything moved in a loop until one of us could gracefully exit.
The problem is not depth for depth’s sake. I had really nice conversations about nothing of importance—about the movie, about the neighborhood, about the weird physics of sourdough. The conversations that drained me were not shallow; they were inert. Nothing new could be entered. No one would say anything that would surprise me. He had no intention of growing up.
Now I think of it less and more like depth and shallowness movement. A good conversation moves somewhere. It can end up where no one expects. That movement—that little feeling of not knowing where this is going—is what I miss and mislabel as personal failure.
I missed the turn
I finally realized: I had been a passive participant in a format I didn’t enjoy, and then blamed myself for not enjoying it.
Instead of doing something to make the conversations interesting, I waited for them to be interesting. I assumed that the social rules were set – I was supposed to reply “well, busy, you know how it is” when someone asked how things were going, that I was supposed to stay in the approved lanes. I didn’t realize I could… no.
Not rude. Not with the obligatory depth of someone who has just discovered philosophy. But with real interest.
When I actually started answering questions honestly – instead of saying, “well, busy, you know how it is,” something changed. People either quickly disconnected (which was fine) or leaned in. And then we were together.
I started asking different questions. Not necessarily deeper questions – just questions that really interest me. “What made you want to do that?” instead of “Oh cool, how long have you been doing this?” The first question invites the person to reveal something about himself. The second just confirms a fact.
Sounds like a minor fix. It has changed almost all my social relationships.
What I thought was actually happening
Looking back, I think two things were happening at the same time.
The first was that I naturally preferred conversations where something was resolved, where ideas clashed, where any of us could change our minds, and where there were genuine interests. This preference is not unusual. Many people share this and mislabel it as social anxiety or introversion for years.
The second was that I completely abdicated my role in shaping the conversations. I took each exchange as an event that happened for more me than something I co-created. When the conversation went bad, I assumed it would be how it would be. I never thought about what I could present, channel, or slowly unfold.
Together, these two things created my experience: someone with a high preference for good conversation and zero sense of personal agency in achieving it is ill-suited to a world full of people who enjoy walking around in social situations and talking to each other.
I wish someone had told me earlier
You don’t have to find every chat format attractive. Some people really love small talk—its light friction, its social warmth, its ritual reassurance that you’re both still here and okay. It is real and reliable. But if you’re someone who finds it draining, it’s not a character flaw. It is an advantage.
What does What you do with that advantage is in your control. You can use it to excuse yourself from all social endeavors, or you can use it as a compass to guide you toward the kinds of exchanges that truly nourish you and motivate you to have more conversations in that direction.
People I know who light up every room they walk into are not universal in conversation. They are great at finding a frequency that works for them and dialing it in quickly. Some do it with humor, some with vulnerability, and some with a well-timed question. But they all steer in one way or another.
For years I sat in the passenger seat and wondered why every trip felt the same.
Now I ask better questions. I give more honest answers. I’m willing to let the conversation go somewhere unexpected, and I’m willing to direct it myself when it doesn’t go anywhere.
I’m still not the person who works in every room. But I’m not one to leave every party wondering what happened to me anymore. I just had to realize that I blamed the driver when I wasn’t even driving.
