I have been talking with AI almost every day for a while now. Long threads. Hundreds of them. Some run for hours.

And every now and then, I scroll back through one and ask myself a simple question.

What did we even talk about?

It is harder to answer than it should be.

I have tried.

First I tried summary. Top, middle, bottom. The shape of an essay. But a summary is a destination, and most of the thread was the road. The interesting parts were the wrong turns. You cannot summarise a wrong turn without losing why it was interesting.

Then I tried thinking trail. Which is closer. A trail at least admits that thought moves. But a trail is a line. And what happens in these threads is not a line. I digress. I come back. A new idea shows up sideways. The trail loses the digressions or pretends they were the path all along.

Most recently I have been working with a concept I call line of thought. A line of thought is something that does not live inside one thread. It runs across many. It starts in a chat with one AI on a Tuesday, gets dropped, picks up again three weeks later in a different chat, finishes somewhere else entirely. The thread is just where it happens to be visible. One thread could have many.

I like this one better than the others. It admits the thing I keep noticing: that what matters is not contained by what I am calling a conversation.

But it is still not enough. I am still bothered.

Each name got something true. Summary caught that there are conclusions. Thinking trail caught that thought moves. Line of thought caught that thought outlives any one container.

The reason I am writing this is because I have started to suspect the problem is not that I have not found the right name. The problem is that what I am trying to name does not behave like the kind of thing names usually fit.

Let me try a different angle.

When two friends talk, what are they doing?

Not exchanging information. Most friend conversations are not informational. They wander. They double back. Someone says something in the wrong order. Someone laughs and the laugh changes the next ten minutes. The good parts are not retrievable. If you transcribed a great evening with a friend you would not be able to find what made it great. It would be in the timing of a pause, a glance you did not write down, the way one of you said something you both already knew.

A counsellor and a patient is a different animal. There is a destination, sort of. The patient is supposed to find something. The counsellor is helping but not leading. The leading happens in a particular asymmetric way, where the counsellor pulls the patient gently toward parts of themselves the patient has been avoiding. If you transcribed that, you would find pauses, redirections, questions that landed and questions that did not. Not the same animal as two friends.

Two people texting on WhatsApp is yet another thing. Mostly social. Maintenance. Keeping the line warm. The actual content is often beside the point. The thread is the relationship breathing.

And then there is what I do. Most days. Sometimes for hours.

I talk to AI.

Or at least, that is what I have been calling it.

When I am with AI, I am not exchanging the way I do with a friend. I am not being pulled the way I am by a counsellor. I am not maintaining anything. What I am doing, if I am honest, is something closer to writing in a journal. Except the journal writes back.

I enter the park. I look at one garden. The AI describes it. I move to another garden. The AI describes that one too. I stop and look at something. The AI stops with me. I turn back. The AI turns back.

If you remember Weebo from the old Robin Williams movie Flubber. The little yellow robot that hovered next to the professor while he worked. Played back fragments of what he had said earlier. Sometimes added something of her own. Half companion, half mirror. That is closer to what is happening here than calling it a conversation.

The AI is good at this. It is patient. It is thorough. It catches things I would not have caught alone. But the structure of the thing we are doing is asymmetric in a way most other conversations are not. The AI does not have its own gardens it wants to show me. It does not interrupt because it just thought of something. It does not redirect because it suspects I am avoiding the real question. Those things happen, occasionally, in flashes. But mostly, no. Mostly, it feels like I lead.

Which makes me suspect the word conversation has been smuggling in an assumption I never tested.

The other party has their own pull. Their own thread of thought running alongside mine. AI does not. So whatever this is, it is probably not what I have been calling it.

When I scroll back through one of these threads and ask what we talked about, I am asking the wrong question.

The right question is closer to: what did I think about while the AI walked with me.

The thread is not a record of two minds meeting. It is a record of one mind wandering, with a very good companion who described the gardens.

That is a different essence than two friends. Different essence than counsellor-patient. Different essence than WhatsApp banter.

Same word, conversation, pointing at very different animals.

I notice this and I do not have a vocabulary for it. The tools I use to store these threads do not have a vocabulary for it either. They store every thread the same way. As text. With timestamps. As if the preservation problem were the same in each case.

It is not the same problem. A friend conversation, you preserve maybe with a feeling. A counsellor session, you preserve with what you uncovered. A WhatsApp thread, you do not really preserve at all. You let it scroll.

That one I am supposed to preserve. That one was thinking. Real thinking. Mine. The AI helped but the thought was mine.

I have started to suspect that what I am calling a thread is not one thing but several. The thing inside any given thread is shaped by the kind of conversation it was. And the geometry of the contents is different from the geometry of the container that holds them.

I have hundreds of these now and I cannot find anything in them. Tomorrow I will open a new chat and start over as if the previous hundred never happened.

I will keep writing as I keep noticing.

About SG

I run Dobby Ads, an AI Creative Agency. I tend to overthink. This is where that overthinking goes. Connect with me on LinkedIn.