You leave a conversation thinking it was one of those rare, genuinely meaningful exchanges. The kind where something shifted. Later, you mention it to the other person. They remember the conversation fondly enough, but the moment you’re referring to — the one that rearranged something inside you — doesn’t even register for them. They had their own moment. You were there for it. You don’t remember it at all.

Jesse Danger describes discovering exactly this through a deliberate exercise:

“I do an exercise with my wife, where we write down the moments that struck us most deeply. And there are different moments. And you remember, like, oh yeah, I was there. It didn’t strike me. But now, I’m starting to understand that that was really an important moment for you.”

There’s something quietly destabilizing about this. We tend to assume that a shared experience is a shared experience — that two people in the same conversation are having the same conversation. The discovery that depth lands differently for each person challenges a foundational assumption about what connection actually means.

We commonly talk about deep conversation as though it were a property of the exchange itself. This conversation was deep. That one was shallow. As if depth were baked into the content, the topic, the words chosen. Pick an important subject, ask vulnerable questions, share something real — and depth follows.

But Danger’s exercise suggests something more unsettling: depth isn’t a feature of the conversation. It’s a feature of the experience each person has within it. And those experiences can diverge completely, even when the conversation itself is shared.

Craig Constantine pushes on this during the same exchange, wondering whether a conversation can be considered deep if only one person experiences it that way. His instinct says no — that depth requires both people to feel it. But the evidence points in a different direction. The moments that struck Danger most deeply didn’t strike his wife the same way, and vice versa. The depth was real for each of them. It just wasn’t the same depth.

This matters because it disrupts the engineering model of conversation — the belief that if we choose the right topic, ask the right questions, create the right conditions, depth will reliably emerge. We can certainly create conditions that are more hospitable to depth. But we can’t control where it lands or what it does when it arrives.

Consider how this plays out in everyday interactions. You prepare carefully for an important conversation with a friend. You bring up the thing you’ve been meaning to discuss, the topic you’re sure will matter to both of you. The conversation goes well. But later, your friend mentions something offhand you said near the beginning — something you barely remember — and tells you it changed how they think about their work. Meanwhile, the carefully prepared topic? Pleasant enough. Not particularly memorable for either of you.

Depth, it turns out, is less like a target you aim for and more like weather. You can check the conditions and dress appropriately, but you can’t schedule a thunderstorm. The moments that shake us loose tend to arrive sideways, uninvited, in the gaps between what we planned to talk about.

Danger and Constantine arrive at this together: depth is “experiential, not content.” Constantine imagines repeating the exact same conversation, word for word, and finding it profound the second time but not the first — or the reverse. The content didn’t change. The receptivity did.

This reframes what it means to be good at conversation. If depth can’t be engineered through content, then the skill isn’t in choosing the right topic or asking the most penetrating question. The skill is in receptivity — remaining open enough that depth can find you when it arrives. And perhaps equally important: accepting that the other person’s experience of the same conversation may be entirely different from yours, and that this isn’t a failure of connection. It might be its nature.

Danger’s exercise with his wife points toward something generous. Instead of assuming shared experience, they made space for different experience. They compared notes. They discovered that what was profound for one was background noise for the other. And rather than treating this as a gap to close, they used it to understand each other better — to “help us make more deep and powerful moments for each other.”

That might be the real insight. Not that we should stop trying to create depth, but that we should stop assuming we’ll know it when it happens — or that the other person felt what we felt. The conversation you think was ordinary may have quietly changed someone. The one you treasured may have passed right through them. Neither of you is wrong. You’re just standing in different parts of the same river.

This field note references the Open + Curious episode “Depth versus aliveness,” published June 20, 2024.

This work was produced using AI language models directed through an editorial system designed by Craig Constantine. The author selected all source material, designed the creative framework, directed the editorial process, and made all acceptance and revision decisions. The prose was generated by AI under sustained human editorial direction.