The Conversation Menu: 50 questions worth asking the people worth knowing
On the lost art of talking to each other
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The Conversation Menu: 50 questions worth asking the people worth knowing
I know people who are genuinely gifted at small talk. One of my best friends can walk into any room, read it in thirty seconds, and be mid-conversation with a stranger before I’ve even figured out which corner I’d like to stand in. It’s a real skill, and I mean that without a single ounce of sarcasm. I’ve watched people do this and have been quietly in awe of it my entire adult life.
But for the rest of us, small talk is a special kind of purgatory. It’s not that we’re antisocial or bad at conversation, it’s that the ritual of talking at length about nothing, of cycling through the same six questions like we’re all reading from the same script, feels like a colossal waste of the one resource we can’t get back. There’s a heavy kind of exhaustion that comes from saying nothing for two hours. I would rather sit in silence than perform the weather conversation one more time, and yes, I’m aware that makes me difficult to seat at dinner parties.
But to me, small talk isn’t connection. It’s the social lubricant that keeps us from having to say anything real while we figure out if the other person is safe enough to say something real to. Which is fine, as far as it goes. But somewhere along the way we stopped treating it as a warm-up and started treating it as the whole show. The weather, the weekend, what do you do, oh, how long have you lived here?? The same six questions on rotation until someone checks their phone and we all agree to stop pretending.
I miss actual conversation. I miss sitting across from someone and leaving two hours later knowing how they actually think, what’s shaped them, what they want and haven’t said yet. I miss the version of talking to people where you walked away changed by it in some small way. And I don’t think I’m alone in this, because everywhere I look people are saying they’re lonely while also spending enormous energy avoiding the exact thing that would fix it.
Part of what’s made this worse, I think, is the political climate we’ve all been marinating in for the last decade. We’ve been trained, very deliberately, to treat disagreement as a form of aggression. To see someone who holds a different view not as a person worth understanding but as a threat to be managed or a problem to be corrected. Platforms have built entire systems around this logic, curating what you see and don’t see, flattening the discourse until everyone in your feed agrees with you and you start to think that’s what the world looks like.
Bluesky recently made a post about how they’ve been “working hard” to make their platform “less toxic,” which in practice means less of the speech they find uncomfortable. I’m not naive about how these decisions get made, and I’m not interested in debating specific platforms here, but I do think it’s a symptom of something real. We’ve built an entire media infrastructure around the idea that being challenged is harm, and we’re shocked that people have stopped knowing how to be challenged.
What this has done to actual conversation is devastating. Changing your mind used to be called thinking, but now it’s called flip-flopping. It’s social suicide in certain circles to admit you were wrong about something, because it opens the door to everyone who disagreed with you marching back in to say they knew it all along. One of my favorite quotes—often attributed to John Maynard Keynes, the economist whose ideas basically rewrote how governments think about money—is apparently one he never actually said. But whoever did say it nailed something important: “When the facts change, I change my mind. What do you do, sir?”
The willingness to update is the whole point of having a mind, but we’ve made it costly in a way it’s never been before, and people have responded by becoming more rigid, more defensive, and much less interesting to talk to.
*Taps sign*
This is also (I want to be very clear here) not a problem that belongs to any one side of the political spectrum. I’ve watched people on the left refuse to engage with any data that complicates their preferred narrative and I’ve watched people on the right do the exact same thing with equal conviction. The issue isn’t ideology, it’s the fact that for a lot of people their opinions have become load-bearing parts of their identity, which means examining them feels like structural damage. The moment someone disagrees with you stops being interesting and starts being a personal attack.
This Conversation Menu isn’t really a cure for any of that, but it is an alternative to participating in it. I organized these questioins by what they actually reveal about a person, like how they handle being wrong, whether there’s a gap between what they perform and what they actually believe, how they think, what they want, how they see other people, and what they’ve survived. They’re not designed to make people uncomfortable for fun, they’re designed to make it easy to have the kind of conversation that most of us are quietly starving for.
Quick note before you dive in: some questions will get you honest answers and some will get you a person’s preferred narrative about themselves. For example, almost everyone, when asked how they respond to disagreement, will say they try to understand the other perspective, because that’s who they want to be, not necessarily who they are. I’ve kept some of those questions in because even a person describing the version of themselves they wish they were tells you something. But the sharper questions are always the behavioral ones, the ones that require a specific story, or naming something that actually happened, because those are much harder to fabricate on the spot, and that’s usually where the real conversation starts.
One more thing: real curiosity is economical. The best questions are short. You ask the stripped-down version and let the silence do the work, because a long, over-specified question tells the other person exactly what kind of answer you’re looking for, and then that’s what you’ll get.
What’s inside → 6 categories of questions:
How they handle being wrong
What they actually believe vs. what they perform
How they think
What they want
How they see other people
What they’ve survived
Plus a bonus set of my personal favorites
50 questions total, each with a short note on what the answers reveal
Use this however it works for you. First dates, long drives, dinner parties, whatever. These aren’t meant to be ran through in one sitting. Just pick one or two from wherever the conversation naturally wants to go, ask it like you mean it, and then actually listen to the answer. I think we might be pleasantly surprised by other people if we give them the opportunity to do so.
Karl Popper’s entire philosophy of science was built on a single uncomfortable premise. He believed what separates genuine knowledge from dogma isn’t how strongly you believe something, it’s whether you’re willing to have it proven wrong. He called it falsifiability, and the idea was radical enough that it reorganized how we think about what science even is. A theory that can’t be disproven isn’t knowledge, it’s faith. And a mind that can’t update isn’t thinking, it’s performing.
See also:
The willingness to be wrong is one of the most underrated measures of a person we have. Most people treat their opinions like personal property, which means any challenge to the idea registers as a challenge to them. The people worth knowing have figured out that changing your position is a sign of engagement, not weakness. These questions find out which kind of person is sitting across from you.
What’s the last thing you actually changed your mind about?
What do you think you’re probably wrong about right now?
What's the most expensive opinion you've ever had? (Expensive meaning it cost you a relationship, money, time, reputation, etc)
When someone disagrees with you, what happens in your body?
Have you ever gone looking for something that might prove you wrong? What did you find?
What's a belief you've been quietly walking back for years but haven't said out loud yet?
Who’s someone you love disagreeing with? What makes it not terrible?
What’s something everyone around you accepts that you think is wrong?
What these questions reveal: intellectual honesty and ego flexibility. Specificity is the tell. If they can name the actual belief and what cracked it, that tells you almost everything. “I’ve grown a lot” tells you nothing. Grown how? In what areas? What was your starting point?
Hannah Arendt wrote extensively about the difference between public and private life, arguing that a healthy society depends on keeping the two from collapsing completely into each other. When they do collapse entirely, when everything you believe privately is identical to what you’re willing to say publicly, it’s not integrity, it’s actually conformity. The most interesting people have a private life of the mind that doesn’t always match their public one, not because they’re dishonest, but because they’re actually thinking, and thinking doesn’t always produce socially acceptable conclusions on the first pass.
Most people have adopted the positions of their social environment because it’s the path of least resistance. The cross-ideological questions live here, and they produce the most genuinely enjoyable conversations because they don’t belong to any tribe. These are the questions that can make dinner tables across party lines actually interesting again.
