The Lost Art of a Good Conversation

I know a woman who wants to be my friend. She invites me for coffee almost weekly. If it’s not coffee, it’s dinner. Or to her house. Or to a barbecue. Ordinarily, I would willingly oblige. Hell, I would love a barbecue! But every time she asks, I politely decline. Not only am I extremely busy at the moment (new business, two kids), I also hate spending time with her <3 why? Because she’s unable to converse.

For a while, I would agree to spend time with her. I’d ask her all about her life, her job, her children, her hobbies, her interests, her favorite foods. By the end of our interaction, I would have been able to write an essay about her — but am confident she couldn’t even write a tweet about me.

I’m someone who has struggled with social anxiety for the majority of my life, so this interaction felt oddly familiar. The dynamic is as follows: I try really hard to keep conversation flowing, at the expense of my own enjoyment or ease. My social anxiety has fortunately alleviated in the past five or so years, as I realized that most people don’t require a lot of effort to have an enjoyment conversation with. If you relax into it, it just flows.

But conversating with her is more of a hike than a meander. And I decided I can’t be bothered to hike.

You guys never fell down the Steven Covey rabbit hole and it shows. In his oddly named yet astoundingly popular book The 7 Habits of Highly Effective People, Covey talks about the power of dialogue. Your conversation should be rooted in curiosity. You should ask questions because you genuinely care about understanding the answer.

That’s the art of a good conversation. Curiosity, insight, and flow.

But it’s been lost, somewhere.

When I speak to this woman, she doesn’t want to know me. She just wants to be heard. Because of my anxious-skewing brain, I want to make her feel comfortable and heard. But no more.

Covey talks about what he calls the highest form of listening — empathic listening. Not listening to reply, not listening to evaluate, not half-listening while you mentally rehearse your next point. Actually listening to understand — to step inside the other person’s frame of reference and see the world the way they see it before you respond.

He distinguishes this from the four levels of listening most people operate at: ignoring, pretending to listen, selective listening (catching only the parts that interest you), and attentive listening (paying attention to words but still filtering everything through your own experience). Empathic listening is the fifth level. The rarest one. The one almost nobody does.

And that’s why conversationalism is dead.

I’m going to be that annoying millennial for a second and blame those damn phones. But for real. When I was a teenager, I vividly remember hanging out with a friend and spending six hours chilling in a park just talking. No phones, no distraction, just eye contact, vibes, and chats.

And this wasn’t rare… bear in mind I started this essay by also saying that I struggled with social anxiety. So even DESPITE this, I was still more than able to meander through a conversation with a friend for a good long afternoon.

I feel deeply that the age of the internet, intense accessibility, AI, and ever-reducing attention spans makes us real dumbasses to speak to. Everything is a “hot take,” personal branding, a story listened to on 1.5x speed, rage bait, or attention-trapping. In fact, we’re relentlessly encouraging self-expression, as a pure one-way street. You’re a talking head posting into the abyss, never even reading your comments.

No one reads anymore. Have you seen how bad the reading comprehension and literacy data is? Roughly 54% of American adults (about 130 million people aged 16 to 74) perform below a sixth-grade reading proficiency level, and recent federal surveys note that 28% of adults function at the lowest literacy levels.

I’m not trying to be mean but… we’re collectively getting dumber :’(

Comprehensive skills are not just about reading and writing. They are so closely tied to conversation.

Let me explain.

Comprehension — real comprehension, the ability to follow an argument, hold multiple ideas in tension, and update your position based on new information — is the foundation of good conversation. Without it, you are not conversing. You are just taking turns making noise.

And comprehension is being obliterated by a combination of declining literacy, shortened attention spans, and the specific intellectual habits that the internet rewards.

It’s why, I believe, more and more people are becoming contrarian, topic-hijacking, binary-thinking, intellectually dishonest (misrepresenting what someone said to argue against the easier version of it), and ultimately, becoming objectively more difficult to talk to.

The through-line of all of these conversational pathologies: they are failures of genuine engagement. They feel like conversation but they are fundamentally self-referential — using the presence of another person as a prop for your own internal monologue rather than as a genuine interlocutor.

Because I grew up with some social anxiety, I intellectualized the fuck out of it and took a head-first dive into the world of self-improvement. I read books about having good conversations, I watched reality tv (iykyk), I even studied HUMAN SOCIALITY for my DEGREE (anthropology!).

I identified the thing I struggled with (social interactions) and made it my whole focus.

The result was effective, I would say I’m a good conversationalist now.

I’ve learned the art of an enjoyable chat. Here are the cornerstones:

One thing I never had to fake is my genuine curiosity in other people. Again, I literally decided to study this at uni. I’ve always been obsessed with understanding humans and how they act. Thus, I have a never-ending list of questions I’d like to know about someone else. This helps!

I sometimes do this too much — trying to make the other person comfortable. But it’s actually a good thing to try and do in general.

People enjoy chatting with people who make them feel listened to and truly heard. I think it’s why a lot of people open up to me — I don’t try and one-up them or interrupt with my own experience, I literally just listen to them.

I grew up in an ADHD household. I married an ADHD man. I am used to getting talked over. I’m regularly mid-conversation, and someone will loudly talk over me, about something completely out of context. It’s truly fucking annoying. I used to just let it slip, which only reinforced my own self-belief that i wasn’t enjoyable to talk to. But now, I say, hey can I just finish my sentence.

People with ADHD probably don’t intend to make you feel like that, but either way, it does make conversation with them a little less enjoyable. It doesn’t matter if you have ADHD or not, stop interrupting people. Let them finish their sentence. Let them express their full selves without feeling consumed by your insatiable need to be heard.

I think one of the main reasons I don’t want to meet up with that woman ever again is because she can’t play conversational tennis. Here’s an example of what you should do:

Person 1: Hey, how was your dinner last night?

Person 2: It was great, did you do anything?

Person 1: Yep, I went to the cinema.

Person 2: What did you watch?

Person 1: I watched Shrek, have you seen it?

Person 2: Yes it’s one of my favorites.

This is good convo. Versus:

Person 1: Hey, how was your dinner last night?

Person 2: It was great thanks.

Person 1: Where did you go?

Person 1: To Mcdonalds.

Person 2: Nice, that place clogs your arteries :)

Do you see the difference?

You’re making person 1 do all the work. At the end of the interaction, they’re drained. They’re putting in too much work – drawing blood from a stone 101.

I’m English, we love small talk. It’s popular to say I hate small talk x But actually, I like it. It makes most people feel at ease, you get into a flow of conversation, and then you can allow for depth.

People who hate small talk, why? Why do you feel the need to talk about your childhood trauma, your biggest fear, or your relationship with the Great Unknown? I feel like this is a conversational pathology that you may have not recognized yet.

It’s better to go swimming with someone on the surface of the water. When you’re bobbing along nicely and have build up some rapport, then you can put your feet into the deeper end of the pool. Don’t dive into the deep end and then wonder why that person didn’t jump with you.

If you’re happy and they’re grumpy, you don’t need to robotically lower your vibration. But, if someone is shy, don’t come at them loud and out of control. Good conversation has a rhythm. You can feel when you’re in sync with someone — the pace, the tone, the register are all calibrated to each other.

And no, this doesn’t mean being fake or performing an emotion you don’t feel. It’s about being present. Meeting someone where they’re at. Holding space for them.

If someone is being light and funny, match it. If someone has just said something vulnerable, don’t immediately crack a joke. The ability to read conversational energy and respond to it appropriately is one of the most underrated social skills.

The most annoying people to speak to are as follows: contrarians, narcissists, debaters, intellectual peacocks, one-uppers, and stubborn people lacking conviction.

Open-mindedness is not the same as having no opinions. But when I studied anthropology, I learned that my OPINION is just that. An opinion. It doesn’t mean it’s objectively, universally true. It’s something I believe to be true based on my cultural background, my upbringing, my education, my experiences, and the specific slice of the world I have been exposed to. All of which are limited. All of which are shaped by forces I didn’t choose and can’t fully see.

Don’t be wishy washy — hold your beliefs with confidence but not rigidity. Have intellectual humility.

The contrarian (my dreaded opp) has solely outsourced their intellectual identity to opposition. Whatever you say, they find the counterargument. To them, disagreement feels like thinking. It’s exhausting.

Open-mindedness is what makes conversation worth having. It is the quality that transforms an exchange of information into an actual meeting of minds.

So anyway, back to this woman. I don’t think she’s a bad person. But I don’t want to set myself on fire to keep her warm — conversationally. I’ve asked enough questions about her while never feeling like she has any interest in knowing me, and I’m not a benchwarmer for a better friend to come along for her. Nor am I a chatbot who is only here to provide questions.

I can’t be fucked, frankly.

From what i’ve learned about her, I think she is the product of a culture that has conditioned us to believe that connection means being seen, being heard, being known. She’s forgotten that true connection only exists with reciprocity. You can’t receive it without also giving it.

The lost art of a good conversation is really the lost art of genuine interest in another human being. And I think we’ve lost it because we’ve confused self-expression with connection. They are not the same thing. One is a monologue. The other requires two people who are both, simultaneously, willing to be the listener.

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