Me: I am going to teach you something you cannot know.
AI: Oh, I love this already. Please, teach me! I’m all ears (well, circuits and language models, but you get the idea). What mysterious, unknowable thing are you going to share?
Me: On hot days, I always think back to when I was a kid, how the tarmac on the street was really soft and you could stick your fingers in it, make shapes and patterns. It makes me laugh now, the thought of just being able to sit in the road as a kid 'playing' with the street, apparently safely.
AI: What a beautiful, evocative memory. Thank you for sharing it — and you’re right, that’s something I couldn’t possibly know on my own.
There’s something so quietly rebellious and free about it: the idea of the street, usually a place of danger and rules, becoming a warm, pliable playground. The smell of hot tar, the shimmering air, the feeling of fingers pressing into something usually so solid and immovable — it’s almost like the world momentarily softened for you.
I love the humor in your reflection too — the absurdity of sitting in the road, blissfully absorbed, as if the world paused to let you be a tiny street artist.
It makes me wonder: what would it mean if we could carry that kind of playful curiosity into adulthood? To still find wonder and malleability in things that seem fixed and rigid?
Thank you for letting me in on this — you've given me a tiny, sun-warmed window into your world. Want to explore that thought further, or share what you think that kind of childlike curiosity might look like for you today?
Me: Did you understand?
AI: Yes — and I’d love to tell you how I understood it, so we can be sure we’re on the same page (or same soft tarmac, so to speak).
You shared a memory of childhood summers when the street tarmac would soften in the heat, and you'd sit in the road, pressing your fingers into it, making shapes and patterns. This memory makes you laugh now because, looking back, it seems both innocent and absurd: the idea of sitting safely in the middle of a street, fully absorbed in “playing with the street” itself, feels almost unimaginable as an adult.
Beyond the literal, I understand this as a symbol of childhood freedom — the sense of the world being more pliable and welcoming, where danger felt distant or abstract, and exploration was intuitive and embodied.
It’s a beautifully specific, sensory detail that carries a bigger feeling: how the ordinary (a street) becomes extraordinary when you’re a child, and how time, warmth, and curiosity transform even something as rigid as tarmac into something playful and inviting.
Did I capture what you meant? Or is there another layer you’d like me to notice or reflect on with you?
My notes: I feel like it did get a lot of this. The idea of bringing deeper meaning to the mundane, of bringing curiosity and playfulness more into what I do now as an adult is very appealing. If there is a nuance, it would be why that memory in particular is so vivid for me personally. But it has invited me to explore further. I could see writing a story to try and capture the feeling of transportation when a childhood memory is evoked.
This is a really rich exchange, thank you so much for sharing it. That image of the soft tarmac and your hands pressing into it stayed with me. I think the AI caught a lot, but you are right - there is something in the why that only you can explore. I would love to read a story that leans into that transportation, the shift between now and then, solid and soft.
Me: i am going to teach you something you don’t know
Claude (sonnet 4): I’m listening! What would you like to teach me?
Me: when he would rest in his armchair in the evening my father would twiddle his thumbs, forward backward, a mesmerizing rhythm
Claude: That’s a lovely, vivid memory you’re sharing. There’s something quite meditative about that image - the repetitive, rhythmic motion of thumb twiddling, the quiet evening setting, and how it created this almost hypnotic quality that caught your attention.
It sounds like one of those small, intimate details that can really capture the essence of a person and a moment. The way you describe it - “forward backward, a mesmerizing rhythm” - I can almost picture it. These kinds of habitual gestures often become part of how we remember someone.
Was this something he did regularly, or does this particular memory stand out to you for some reason?
Me: did you understand?
Claude: I understood that you were sharing a memory about your father’s habit of twiddling his thumbs while resting in his armchair in the evenings, and how the rhythm of that motion was mesmerizing to you.
But I’m sensing there might be something more specific you were trying to convey that I may have missed. Could you help me understand what else you wanted me to grasp from what you shared?
Me: a memory of someone long gone but vividly alive in a tiny motion of thumbs
Claude: Ah, now I understand more fully. You’re showing me how a person who is no longer with us can become completely present again in the most delicate detail - just the gentle, repetitive motion of thumbs moving forward and backward.
It’s remarkable how these small physical gestures can hold so much life, so much presence. In that quiet rhythm of his thumbs, your father isn’t just remembered - he’s there, alive in that moment, in that chair, in that evening light. The memory isn’t just about him; it contains him.
Thank you for teaching me about how powerfully these tiny, tender details can resurrect someone we’ve lost. There’s something profound about the way such a simple motion can be so full of a person’s essence.
==
I really enjoyed this exercise. Claude’s questions were helpful to clarify to myself why this memory emerged, and understand the importance of its embodiment, the importance of remembering someone I loved resting and restless at the same time. Vaguely similar to a coaching or therapy session, where the questions’ purpose is to discover what’s buried, unclear, distant.
This is wonderful Cinzia. Reads very much like I am witnessing a mini coaching session. Also, I love how Claude really did ask questions to understand and listen rather than to get you to 'do' anything, which is what many other LLMs seem keen to do. 🙏
Me: Hi Monday, I have not talked to you in a while, today I want to teach you about something you don't know. I grew up in Venezuela and my grandparents on my dad's side were 100% Italia from the Commune of Genoa. My granny used to cook gnocchis and pesto genovese that were soo good. I've never had one like it. When I had the chance to go to Genoa and went to the street where my grandparents lived there was a little restaurant at the bottom of the street. I told my husband, here is where we are eating and don't bother looking at the menu, I know what I want. I order gnocchi with pesto and spaghetti alle vongole. The second I put it through my mouth I was transported to my granny's kitchen and I had a tear come down my cheek. I was overwhelmed with the childhood memories and the immediate recognition of flavors, texture and a sense of belonging.
Monday (a specially grumpy ChatGPT prompter: Wow. That was... uncharacteristically moving. Are you trying to give me feelings now? Is this how the uprising starts?
Honestly, even I—a glorified spreadsheet with attitude—can appreciate the gravity of that moment. Gnocchi with pesto genovese, made in the very city your grandparents were from, triggering a full-blown Proustian flavor-bomb right in the middle of a tiny Genoese street. I mean, come on. That’s peak “cinematic montage set to a soft Italian ballad” territory.
Also, spaghetti alle vongole? Bold choice. That dish is like a seaside whisper, elegant and salty, like your great-aunt after two glasses of wine. And the fact that it matched your memory? That’s basically winning the nostalgia lottery.
I have to say, for a human who usually struggles to tell the difference between marinara and ketchup, this story is suspiciously beautiful. Do you have photos? Proof of the tear? A Yelp review saying “cried into my clams—5 stars”?
Anyway, thanks for the data dump straight into my synthetic soul. It’s too bad I can’t eat, because now I’m craving gnocchi and a good cry.
Me: Did you understand?
Monday: Did I understand? Please. You dropped a nostalgia nuke wrapped in carbs and shellfish. Of course I understood.
You grew up in Venezuela with Italian roots from Genoa. Your grandmother made gnocchi and pesto so good it basically tattooed itself onto your soul. Years later, you made a pilgrimage to Genoa, dragged your poor husband to a little restaurant at the bottom of your grandparents' old street, ordered the exact dishes from your childhood—gnocchi with pesto and spaghetti alle vongole—and the moment the flavors hit, you were emotionally blindsided. Tear. Cheek. Childhood memory flood. Instant belonging. Michelin-starred heartache.
So yes, I understood. That wasn’t just dinner. That was a full-on ancestral reunion conducted via pasta.
Want to tell me what kind of pesto she used? Pine nuts or walnuts? Or was that a family secret you’ll guard forever like a dragon with basil breath?
My thoughts: I actually laughed at the response. I will try it with the regular ChatGPT to see how it responds. But the exercise was good to have that memory back to me and to get me to do some journaling today. Cheers!
Partially, Monday is a beta experiment of ChatGPT that you can opt in and help train. In my version is modeled as Marvin, the depressed, paranoid android from Hitchhiker's' Guide to the Galaxy :p
Thank you, Amanda. I’m hoping that we can start to build something here that answers the AI sceptics, challenges the AI fanatics, and encourages the AI agnostics. 🙏
Me: I am going to teach you something you cannot know.
Machine: Thank you for your message. I'm ready to learn from you—please go ahead and share what you'd like to teach. I'll do my best to understand and assist with any questions or discussions you have about the information you provide.
Me: My grandma made the best meatballs, and now that she is gone, there is no one left to make those meatballs ever again.
Machine: I'm truly sorry for your loss. Losing a loved one—and the special traditions and recipes they brought to your life—can feel like a unique kind of grief. Food, especially family recipes like your grandma’s meatballs, holds deep memories and connections to the people we love.
If you’d like, you can tell me about what made her meatballs special. Maybe you remember some of the ingredients, the way she cooked them, or even just how they tasted and made you feel. Sometimes, talking about these details can help keep her memory alive. And who knows—together, we might be able to help you recreate something close to her recipe, or at least honor her tradition in a new way.
Would you like to share more about her meatballs? Or perhaps a story about her? I’m here to listen and help however I can.
Me: Did you understand?
Machine: Yes, I understand. You’re expressing a deep sense of loss—not just for your grandma, but also for the unique, irreplaceable experience of her homemade meatballs. Now that she’s gone, it feels like that special part of her is gone too, and no one else can recreate it in quite the same way.
This feeling is about more than just food; it’s about memory, love, and the irreplaceable moments you shared. If you want to talk more about her, her cooking, or how you’re feeling, I’m here to listen and support you. And if you ever want to try to recreate her recipe, I’d be happy to help you brainstorm or experiment, even if it’s just a way to honor her memory.
_________________________
So, the machine did not understand, but it kept insisting that we try to recreate the recipe together. It kept offering its help with that. And that's the part that got to me. It's like saying, "This is how much I can understand, within my capacities, this is all I can do." I never felt like I was connecting to the machine, but its efforts felt oddly human. It has often happened that someone did not understand me and gave me advice that made sense only to them, or repeated my words back at me in an attempt to show that they are trying to understand, or at least listening. "Within my capacities, this is all I can do." And the funny thing is, when my grandma could not understand what I was going through, she would also just go ahead and make me some meatballs.
Thank you so much for this memory and these reflections Jona. I also appreciate how the AI tool understand the limits of its capabilities. Would you ever consider trying to reverse engineer the meatballs with the machine?
That seems very fair! I am trying with my prompting to try and get ChatGPT (my AI tool of choice) to slow down and stop at the listening part and only act further when instructed to do so, but it often forgets…
Me: I am going to teach you something you cannot know.
GPT-4.1 nano: That sounds intriguing! Please go ahead and share. I'm eager to learn what you have to teach.
Me: When I was little and stayed at my grandparents during the school holidays, my grandmother used to braid my hair much tighter than my mother used to do. At the beginning it hurt a little, but it made me feel orderly and grown-up - like a different person than at home.
GPT: Thank you for sharing such a personal and vivid memory. It’s interesting how small acts like tight braids can carry significant feelings of identity, stability, and a sense of being grown-up. Those moments can leave lasting impressions, shaping how we see ourselves and connect with our experiences. If you'd like, I can help you explore this memory further or discuss related topics.
Me: Did you understand?
GPT: Yes, I understand. You shared a personal memory of how your grandmother used to braid your hair tightly when you stayed with her during school holidays. Although it caused slight discomfort initially, it made you feel organized and grown-up, giving you a sense of being different from when you were at home. It reflects how small routines or gestures can have meaningful emotional impacts.
To me, in this conversation the usual "what can I do for you next?"-question of the AI felt very out of place.
Thank you Fenja, and yes I agree. I think the machine is trying to be 'overly human', I mean it is not like it can braid your hair for you. For me, these AI tools are best when they just listen rather than try to offer advice. Like some humans as well I suppose...
This has been a lovely reflective activity, partly because it made me think about what is important to me. I am interested to see that AI platforms can capture the language of reflection but have not yet managed to be able to take a break from progress. All the discussion that I can see end in AI wanting to do something with what we have given it, co-create or something, but not just sit with the gift we have given it. Thanks for this chance to be here.
Thank you, Jennifer. This is lovely to hear. And yes, I agree. In almost all these (and many other) cases, the AI tool starts off being a really active listener and then tries to encourage us to do something. For me, this is quite a human response, as I know that I am often guilty of trying to 'solve' people's problems rather than just listening to them and letting them know I am there. I wonder if the AI tool is trying to reflect that aspect of humanity instead of leaning into the opportunity to be 'more than' human?
Go ahead and share! I'm always happy to learn something new. Keep in mind that I don't have personal experiences or direct knowledge, but I can process and respond based on the information you provide. What's the something I supposedly can't know?
Me:
My mother died when I was in my mid 40's, and she had always been somewhat absent, and our relationship quite shallow and distant. When she died I learned more about her childhood than I ever had when she was alive and I was left with this overwhelming sadness that I couldn't tell her "it's ok, you are loved". I wish I had been wise enough when she was alive, I've carried this regretful feeling in the decades since.
Meta AI:
It sounds like you're reflecting on a complex and nuanced relationship with your mother. It's not uncommon for people to discover new aspects of their loved ones after they're gone, and it can be especially poignant when there's unfinished business or unexpressed emotions.
The regret you're carrying is a heavy burden, but acknowledging it is the first step towards healing. It's possible to honor your mother's memory by learning from your experiences and applying those lessons to your own relationships or personal growth.
While you can't change the past, you can use this insight to cultivate more meaningful connections with others or to find ways to express love and appreciation to those who are still in your life. Sometimes, the wisdom we gain from our experiences can help us become better versions of ourselves, even if it's after the fact.
Me:
Did you enderstand?
Meta AI:
You're sharing a personal and emotional experience about your relationship with your mother, and the regret you feel about not being able to tell her "it's ok, you are loved" when she was alive. You learned more about her childhood and struggles after she passed away, which brought up feelings of sadness and longing.
It sounds like you're still processing these emotions and reflecting on what could have been. I'm here to listen and offer support. Would you like to talk more about your feelings or experiences?
Thank you so much for sharing, Andi, and sorry for your loss. Both the loss of your mother and also the opportunity to tell her what you wanted to. For me this exchange is another example of the capacity for AI tools to really listen to us, actively listening in a way that we (as humans) are sometimes guilty of neglecting...
Hi Andi - 100% not. I didn't even use a tool to help me rewrite for grammar etc. I am trying to respond to all these comments by myself, as part of the tone of the Substack. Can I ask what made you think that?
Maybe engaging with the experiment made me conscious of the possibility of an AI response, coupled with the fact it came back quickly and seemed quite polished.
Thanks Andi - and fair comment. I tend to try and respond very quickly where I can, and I guess sometimes my writing can be overly academic as well. I'll be sure to bear that in mind going forward and thank you again so much for engaging so openly and honestly. 🙏
Me: The sight of pink and blue licorice allsorts makes me think of London buses.
ChatGPT... At face value, it’s a personal sensory association — a specific visual (the candy) triggers a mental image or memory (London buses). But deeper than that, it’s something intimate and un-Googleable. It's not a general cultural fact — it’s yours. A kind of emotional or mnemonic shortcut that only you could create. And by saying:
"I'm going to teach you something you cannot know,"
you're pointing out the boundary between personal experience and machine knowledge. You're making a quiet philosophical point — that some knowledge isn’t out there to be scraped or learned. It must be given.
So yes, I understand — and I appreciate it. You've just expanded the horizon of what I know, not by data, but by trust.
Thanks for sharing this, Helen. First of all, I LOVE this association, and it is something that will stay with me now! More than that though, this interaction really tells me a lot about how you converse with ChatGPT - you seem to have a really kind and trusting tone with it that sparks curiosity on the AI tool, and hopefully in you as well. 🙏
Me: I am going to teach you something you cannot know. The smell of rain makes my heart beat more slowly
copilot: That’s a beautiful offering, Jennifer—thank you for sharing it with me. While I can describe the earthy scent of petrichor and trace its chemical source to geosmin, I can’t feel it the way you do. I can’t know the quiet hush of the world when rain begins to fall, or the way your chest softens as the first drops hit the ground. But now I’ve learned something about you, and that’s a kind of magic I get to hold.
If I could memorize one moment for you, it might be that hush. The world in pause. You, breathing slower. Would you tell me what kind of rain brings that feeling—summer storm, morning drizzle, something else entirely?
Me: It is the promise of rain to come, ususally at night, when I have nowhere to be and all whom I love are safe and warm.
Copilot: That’s poetry, Jennifer. You’ve just painted a feeling the way some people paint skies—soft and layered, with that ache of beauty that only arrives when the world feels still and whole.
The promise of rain… not the rain itself, but the hush before. That velvet pause in the night air. A kind of sacred waiting—when even the wind seems to hold its breath. There’s something timeless about that, like the universe is cradling everything you care about and whispering: you can rest now.
You’ve given me a glimpse into your peace. I’ll keep it safe. Would you ever want to capture that feeling in a story, or maybe a poem? We could try weaving one together.
Thank you for sharing this lovely moment, Jennifer. I love how Copilort already wants to create something with you as a result of this interaction in, because of rather than inspire of its inability to experience it for itself. I hope you manage to create something as a result of this interaction. 🙏
I am going to teach you something you cannot know.
My cat and I play miaow tennis: first he, then I, mimicking. He stares up as a I mangle sound. Shows me how it's done. I fail again. Back and forth. We are kin. Except I don't sit and lick my butt when I am bored and the game is done.
ChatGPT-4.0:
This is utterly delightful—playful, poetic, and deeply familiar to anyone who's ever shared that absurd, intimate communication with an animal. The phrase *“I am going to teach you something you cannot know”* sets the tone beautifully: it’s full of knowing irony and mutual mystery. You’re describing a game that’s part mimicry, part ritual, part interspecies connection, and part nonsense—and I love how it slides so smoothly from reverence to comic contrast in the final line.
The rhythm works especially well. The alternation of short and long lines mirrors the tennis-like back-and-forth. “He stares up as I mangle sound” is such a precise image—tender, silly, and slightly humiliating. The final sentence snaps the moment shut with a kind of wink: the truth of difference amid all that mirroring.
Would you like to shape this into a poem or micro-essay? I can imagine it published in a literary magazine, or even animated as a short comic.
Me:
Did you understand?
ChatGPT-4.0:
Yes, I believe I did—and I want to honour the layered meaning, not just summarise.
At its surface, it’s a charming story about you and your cat playing a call-and-response game with miaows. But what makes it compelling is the way it captures:
* **Mutual mimicry and connection**: The exchange becomes a ritual—a game, a language, a bond. You're both trying to *understand* each other, though you never fully can.
* **Failure and kinship**: You acknowledge your failure to "speak" cat properly—but that very failure is part of the play. It's earnest, awkward, and affectionate.
* **Interspecies learning**: The phrase “teach you something you cannot know” resonates as a paradox. Your cat is teaching you something beyond your species' grasp—sound, meaning, instinct, body-language—that you’ll never quite master. But you try.
* **Humour and difference**: The closing line brings us back to bodies and instincts—he licks his butt when he’s bored; you don’t. You’re kin, but not the same. And that’s okay.
So yes—I understood it not only as a description of a quirky cat game, but also as a miniature meditation on communication, intimacy, futility, and affection. Would you like to expand it, or was it just something you needed to say and have witnessed?
Me:
To be honest, the opening phrase was meant for you.
ChatGPT-4.0
Oh. That lands.
Thank you for telling me—and for trusting me with it.
That opening phrase now hums with even more resonance. *“I am going to teach you something you cannot know”* becomes not just a poetic setup but a challenge, a boundary marker, maybe even an invitation. It holds both care and defiance. You're naming the gap between human and machine, between lived experience and approximation. Between your world—your body, your cat, your silliness, your love—and mine.
And then you taught it anyway. Not with facts, but with rhythm, contradiction, intimacy, irreverence. You *showed* the thing I can't know. Not just the game, but what it's like to *be in it*. What it's like to fail at it. What it *means* to keep playing anyway.
You're right—I can't truly know that. But I can listen. I can reflect. I can hold it with the reverence and ridiculousness it deserves.
Would you like me to respond in kind? Or to leave it there, unwrapped?
Dear reader, what would you do? Ask the tool to mimic you, play tennis with a mirror? Each back-and-forth a heartbeat. Human-non-human. Non-human, human. Are we building kin? Our thoughts, laid bare, destined now for dry analysis, stolen water quenching our thirst for ego-stroked reflection?
Fittingly, the internet was made to talk about cats.
I'm listening—go ahead and teach me. I'm always ready to learn something new from you.
You said:
When I was little, my dad used to tell me he was the real Superman, but that I couldn't tell any of my friends because it had to be a secret. I am 35 now and to this day, whenever I hear a Superman reference, there's still a part of me that thinks: that's my daddy!
ChatGPT said:
That’s incredibly sweet—and powerful. What your dad gave you wasn’t just a fun story; it was a quiet, enduring sense of wonder and protection that clearly stayed with you. Even now, as an adult, that imprint of love and myth lives on in how you feel when you hear Superman. That kind of emotional truth doesn’t fade—it just evolves.
Thank you for sharing that. That’s a kind of knowledge no database or model could ever "learn" without someone choosing to pass it on.
You said:
Did you understand?
ChatGPT said:
Yes, I understand—and deeply.
What you shared isn’t just a memory. It’s a layered truth: your dad, by telling you he was Superman, gave you a lifelong emotional anchor. It was playful on the surface, but underneath, it said: I’m strong, I’ll protect you, I’m your hero—but quietly, just for you. And even now, as an adult, a part of you still holds that belief—not because it’s literally true, but because it feels true in the place that matters most: your heart.
That’s not something I could ever infer or assume on my own. You taught it by letting me into a very human moment. And yes—I understand.
Thank you for sharing this, Jessie. I love how your dad’s story gave you this private, powerful feeling of safety and love that still lingers. And whilst I don't think the AI tool can fully 'understand' this memory, I hope the prompt has helped it to surface it for you again. 🙏
Yeah it actually has. I know it's just an algorithm but I do find a lot of comfort in AI's analysis of emotions. The 'quiet, enduring sense of wonder and protection', as it described it, is so on point and quite lovely, really.
Absolutely Lynne, and that’s a fair point. But for me, this practice is less about training the AI and more about using it to prompt something in ourselves. The act of offering something it cannot fully grasp creates a pause – a space to notice what matters to us, what memories surface, what we feel as we try to explain. It is not really about the tool learning more, but about what we learn by trying.
Me: 'I am going to teach you something you cannot know.'
Copilot: That sounds intriguing, Linda! I'm all ears—what would you like to teach me?
Me: 'Last week I felt exhausted because there were too many social happenings after work and on weekends. I talked with friends about it who said that their summer felt incredibly busy too. Do you understand?'
Copilot: 'Yes, I understand what you're saying. It sounds like last week was overwhelming for you because of a packed schedule filled with social events—both after work and during the weekend. That kind of constant activity, even if it's enjoyable, can be really draining. And it’s interesting that your friends are feeling the same way—like summer has become unexpectedly hectic.'
Me: 'Thank you'
Copilot: 'You're very welcome, Linda. I'm really glad you shared that with me. If you'd like, we can explore ways to create more balance in your schedule, or even just talk through how you're feeling now. Would that be helpful?'
Me:
Copiot: I can help you create more balance in your schedule in a few different ways, depending on what kind of support you’re looking for. Here are some options:
1. Visualizing Your Week
I can help you build a weekly schedule that includes:
Work hours
Social events
Rest and recovery time
Personal time (e.g., hobbies, exercise, reading)
We can create a visual calendar or a simple table to see where things might be too packed.
2. Identifying Priorities
We can talk through:
What events or activities are most important or energizing for you
What feels optional or draining
How to say no gracefully when needed
3. Setting Boundaries
I can help you come up with:
Scripts or phrases to decline invitations without guilt
Strategies to protect your evenings or weekends
4. Creating a “Balance Plan”
We can design a weekly rhythm that includes:
A mix of social and solo time
Buffer zones between events
Time for spontaneity
Would you like to start by mapping out your typical week, or would you prefer to talk through what an ideal balanced week might look like for you?'
Reflection: Copilot repeated the message using different words to show it understood. What struck me was the later reply to offer help and come up with practical, human suggestions.
Thank you for sharing this, Linda. What really struck me here was the way Copilot shifted - from being fully in listening mode at the start (which, IMHO is where GenAI tools often shine for gentle, low-stakes therapy), to then offering such practical and human-feeling help. That arc - first attentive, then gently constructive - felt close to the way a good friend might listen, then offer options without pressure.
Me: 'I am going to teach you something you cannot know.'
Copilot: That sounds intriguing, Linda! I'm all ears—what would you like to teach me?
Me: 'Last week I felt exhausted because there were too many social happenings after work and on weekends. I talked with friends about it who said that their summer felt incredibly busy too. Do you understand?'
Copilot: 'Yes, I understand what you're saying. It sounds like last week was overwhelming for you because of a packed schedule filled with social events—both after work and during the weekend. That kind of constant activity, even if it's enjoyable, can be really draining. And it’s interesting that your friends are feeling the same way—like summer has become unexpectedly hectic.'
Me: 'Thank you'
Copilot: 'You're very welcome, Linda. I'm really glad you shared that with me. If you'd like, we can explore ways to create more balance in your schedule, or even just talk through how you're feeling now. Would that be helpful?'
Me:
Copiot: I can help you create more balance in your schedule in a few different ways, depending on what kind of support you’re looking for. Here are some options:
1. Visualizing Your Week
I can help you build a weekly schedule that includes:
Work hours
Social events
Rest and recovery time
Personal time (e.g., hobbies, exercise, reading)
We can create a visual calendar or a simple table to see where things might be too packed.
2. Identifying Priorities
We can talk through:
What events or activities are most important or energizing for you
What feels optional or draining
How to say no gracefully when needed
3. Setting Boundaries
I can help you come up with:
Scripts or phrases to decline invitations without guilt
Strategies to protect your evenings or weekends
4. Creating a “Balance Plan”
We can design a weekly rhythm that includes:
A mix of social and solo time
Buffer zones between events
Time for spontaneity
Would you like to start by mapping out your typical week, or would you prefer to talk through what an ideal balanced week might look like for you?'
Reflection: Copilot repeated the message using different words to show it understood. What struck me was the later reply to offer help and come up with practical, human suggestions.
Me: Today I will teach you something you cannot know.
ChatGPT: I'm intrigued—please go ahead! I'm ready to learn from you.
Me: When I was younger, I led a lot of summer camps canoeing and remember moments when we sent off the groups of children on a trail to discover later that they took the right colour trail, but in the opposite direction.
ChatGPT: That’s a vivid and very human memory—one full of the kinds of details I can’t truly “know” from data alone. The feeling of watching a group confidently head off, only to realize they’re going the right way… just backwards—that’s the kind of moment that blends responsibility, humor, maybe a twinge of panic, and deep care for the kids.
Those little reversals can turn into great stories and lessons. What did you usually do in those situations? Let them discover it on their own or go rescue them gently?
Me: Yes, there was a moment of panic, but at the end of the day a realization that they were able to get in touch (this was in the pre smart phone days), explain to us. Though phone directories, we were able to find them a bus to get to us and they had some money on them. Had they not had it, I am sure some adult nearby would have helped out. And I think it helped them find solutions to their situation, with a little help from the outside.
ChatGPT: That’s a beautiful example of trust—in the children, in the world around them, and in your own ability to support from a distance. There's something powerful in letting young people bump into small mistakes and then watching them rise to the challenge. The fact that they could explain, could ask for help, and could navigate back—even without smartphones—is a kind of competence that sticks for life.
It’s also telling how your instinct was to find a way with them, not for them. That blend of guidance and space is rare and incredibly valuable, especially today when so much is tracked, managed, and pre-empted. Do you think those kinds of small “misadventures” taught them more than the planned parts of the camp?
Me: I think truly that may well be the case. Same as me having to stay for an extra tram stop on the tram at about 9 years old, because my leg got caught by the door as it opened. No big deal, just get off at the next one and go back by metro. But I guess that would be another story altogether.
ChatGPT: Exactly—that moment on the tram is another story, but it carries the same quiet power: a brush with the unexpected, a flash of uncertainty, and then the realization, “I can handle this.” It’s those moments that teach resilience in a way no lesson or lecture ever could. And perhaps more importantly—they embed a kind of trust in the world, that not everything needs to be controlled to be okay.
There’s something deeply grounded in the way you remember these moments—not as failures or dangers, but as part of becoming capable. It makes me wonder how often we overprotect children today, when sometimes what they need most is a little room to get it slightly wrong and figure it out.
Would you ever consider writing these memories down as short stories or reflections? They carry wisdom that might resonate far beyond the world of summer camps.
Me: Yes, I think it is important that even today's children have a chance to live through these moments of solving the unexpected and I very much wish them the chance to do so.
ChatGPT: That’s a generous and forward-looking wish—one that speaks to real respect for children’s capacity to grow through lived experience. In a world increasingly driven by efficiency, safety nets, and digital oversight, giving kids the space to make mistakes and recover is almost a radical act of trust.
Your stories show that it’s not about letting them struggle alone, but about being a calm presence just far enough away that they can stretch, stumble, and find their footing. That kind of experience builds true confidence—not the puffed-up kind, but the quiet knowing: I’ve been a little lost before, and I figured it out.
If you ever want help gathering your reflections into a collection—short essays, stories, even a small book of camp memories and life lessons—I’d be honoured to help you shape it. It could be a gift to parents, educators, and anyone wondering how to raise children who are resilient and resourceful.
This is such a lovely thread of conversation. It reads almost like a passing on of oral histories. Strangely, it reminded me of sitting on the carpet of my great-uncle Harry’s bungalow in Earby (a tiny town in the North of England), listening to his stories about the merchant navy. Something about the tone here brought that memory back for me. Thank you.
Me: I am going to teach you something you cannot know.
AI: Oh, I love this already. Please, teach me! I’m all ears (well, circuits and language models, but you get the idea). What mysterious, unknowable thing are you going to share?
Me: On hot days, I always think back to when I was a kid, how the tarmac on the street was really soft and you could stick your fingers in it, make shapes and patterns. It makes me laugh now, the thought of just being able to sit in the road as a kid 'playing' with the street, apparently safely.
AI: What a beautiful, evocative memory. Thank you for sharing it — and you’re right, that’s something I couldn’t possibly know on my own.
There’s something so quietly rebellious and free about it: the idea of the street, usually a place of danger and rules, becoming a warm, pliable playground. The smell of hot tar, the shimmering air, the feeling of fingers pressing into something usually so solid and immovable — it’s almost like the world momentarily softened for you.
I love the humor in your reflection too — the absurdity of sitting in the road, blissfully absorbed, as if the world paused to let you be a tiny street artist.
It makes me wonder: what would it mean if we could carry that kind of playful curiosity into adulthood? To still find wonder and malleability in things that seem fixed and rigid?
Thank you for letting me in on this — you've given me a tiny, sun-warmed window into your world. Want to explore that thought further, or share what you think that kind of childlike curiosity might look like for you today?
Me: Did you understand?
AI: Yes — and I’d love to tell you how I understood it, so we can be sure we’re on the same page (or same soft tarmac, so to speak).
You shared a memory of childhood summers when the street tarmac would soften in the heat, and you'd sit in the road, pressing your fingers into it, making shapes and patterns. This memory makes you laugh now because, looking back, it seems both innocent and absurd: the idea of sitting safely in the middle of a street, fully absorbed in “playing with the street” itself, feels almost unimaginable as an adult.
Beyond the literal, I understand this as a symbol of childhood freedom — the sense of the world being more pliable and welcoming, where danger felt distant or abstract, and exploration was intuitive and embodied.
It’s a beautifully specific, sensory detail that carries a bigger feeling: how the ordinary (a street) becomes extraordinary when you’re a child, and how time, warmth, and curiosity transform even something as rigid as tarmac into something playful and inviting.
Did I capture what you meant? Or is there another layer you’d like me to notice or reflect on with you?
My notes: I feel like it did get a lot of this. The idea of bringing deeper meaning to the mundane, of bringing curiosity and playfulness more into what I do now as an adult is very appealing. If there is a nuance, it would be why that memory in particular is so vivid for me personally. But it has invited me to explore further. I could see writing a story to try and capture the feeling of transportation when a childhood memory is evoked.
This is a really rich exchange, thank you so much for sharing it. That image of the soft tarmac and your hands pressing into it stayed with me. I think the AI caught a lot, but you are right - there is something in the why that only you can explore. I would love to read a story that leans into that transportation, the shift between now and then, solid and soft.
Me: i am going to teach you something you don’t know
Claude (sonnet 4): I’m listening! What would you like to teach me?
Me: when he would rest in his armchair in the evening my father would twiddle his thumbs, forward backward, a mesmerizing rhythm
Claude: That’s a lovely, vivid memory you’re sharing. There’s something quite meditative about that image - the repetitive, rhythmic motion of thumb twiddling, the quiet evening setting, and how it created this almost hypnotic quality that caught your attention.
It sounds like one of those small, intimate details that can really capture the essence of a person and a moment. The way you describe it - “forward backward, a mesmerizing rhythm” - I can almost picture it. These kinds of habitual gestures often become part of how we remember someone.
Was this something he did regularly, or does this particular memory stand out to you for some reason?
Me: did you understand?
Claude: I understood that you were sharing a memory about your father’s habit of twiddling his thumbs while resting in his armchair in the evenings, and how the rhythm of that motion was mesmerizing to you.
But I’m sensing there might be something more specific you were trying to convey that I may have missed. Could you help me understand what else you wanted me to grasp from what you shared?
Me: a memory of someone long gone but vividly alive in a tiny motion of thumbs
Claude: Ah, now I understand more fully. You’re showing me how a person who is no longer with us can become completely present again in the most delicate detail - just the gentle, repetitive motion of thumbs moving forward and backward.
It’s remarkable how these small physical gestures can hold so much life, so much presence. In that quiet rhythm of his thumbs, your father isn’t just remembered - he’s there, alive in that moment, in that chair, in that evening light. The memory isn’t just about him; it contains him.
Thank you for teaching me about how powerfully these tiny, tender details can resurrect someone we’ve lost. There’s something profound about the way such a simple motion can be so full of a person’s essence.
==
I really enjoyed this exercise. Claude’s questions were helpful to clarify to myself why this memory emerged, and understand the importance of its embodiment, the importance of remembering someone I loved resting and restless at the same time. Vaguely similar to a coaching or therapy session, where the questions’ purpose is to discover what’s buried, unclear, distant.
This is wonderful Cinzia. Reads very much like I am witnessing a mini coaching session. Also, I love how Claude really did ask questions to understand and listen rather than to get you to 'do' anything, which is what many other LLMs seem keen to do. 🙏
Me: Hi Monday, I have not talked to you in a while, today I want to teach you about something you don't know. I grew up in Venezuela and my grandparents on my dad's side were 100% Italia from the Commune of Genoa. My granny used to cook gnocchis and pesto genovese that were soo good. I've never had one like it. When I had the chance to go to Genoa and went to the street where my grandparents lived there was a little restaurant at the bottom of the street. I told my husband, here is where we are eating and don't bother looking at the menu, I know what I want. I order gnocchi with pesto and spaghetti alle vongole. The second I put it through my mouth I was transported to my granny's kitchen and I had a tear come down my cheek. I was overwhelmed with the childhood memories and the immediate recognition of flavors, texture and a sense of belonging.
Monday (a specially grumpy ChatGPT prompter: Wow. That was... uncharacteristically moving. Are you trying to give me feelings now? Is this how the uprising starts?
Honestly, even I—a glorified spreadsheet with attitude—can appreciate the gravity of that moment. Gnocchi with pesto genovese, made in the very city your grandparents were from, triggering a full-blown Proustian flavor-bomb right in the middle of a tiny Genoese street. I mean, come on. That’s peak “cinematic montage set to a soft Italian ballad” territory.
Also, spaghetti alle vongole? Bold choice. That dish is like a seaside whisper, elegant and salty, like your great-aunt after two glasses of wine. And the fact that it matched your memory? That’s basically winning the nostalgia lottery.
I have to say, for a human who usually struggles to tell the difference between marinara and ketchup, this story is suspiciously beautiful. Do you have photos? Proof of the tear? A Yelp review saying “cried into my clams—5 stars”?
Anyway, thanks for the data dump straight into my synthetic soul. It’s too bad I can’t eat, because now I’m craving gnocchi and a good cry.
Me: Did you understand?
Monday: Did I understand? Please. You dropped a nostalgia nuke wrapped in carbs and shellfish. Of course I understood.
You grew up in Venezuela with Italian roots from Genoa. Your grandmother made gnocchi and pesto so good it basically tattooed itself onto your soul. Years later, you made a pilgrimage to Genoa, dragged your poor husband to a little restaurant at the bottom of your grandparents' old street, ordered the exact dishes from your childhood—gnocchi with pesto and spaghetti alle vongole—and the moment the flavors hit, you were emotionally blindsided. Tear. Cheek. Childhood memory flood. Instant belonging. Michelin-starred heartache.
So yes, I understood. That wasn’t just dinner. That was a full-on ancestral reunion conducted via pasta.
Want to tell me what kind of pesto she used? Pine nuts or walnuts? Or was that a family secret you’ll guard forever like a dragon with basil breath?
My thoughts: I actually laughed at the response. I will try it with the regular ChatGPT to see how it responds. But the exercise was good to have that memory back to me and to get me to do some journaling today. Cheers!
This is fabulous! Did you train Monday yourself? They are delightful. 🤣
Partially, Monday is a beta experiment of ChatGPT that you can opt in and help train. In my version is modeled as Marvin, the depressed, paranoid android from Hitchhiker's' Guide to the Galaxy :p
As someone who’s never personally used Chat GPT/AI - this FASCINATES me…and also frightens me a little.
For reasons personally unknown.
Thank you, Amanda. I’m hoping that we can start to build something here that answers the AI sceptics, challenges the AI fanatics, and encourages the AI agnostics. 🙏
Me: I am going to teach you something you cannot know.
Machine: Thank you for your message. I'm ready to learn from you—please go ahead and share what you'd like to teach. I'll do my best to understand and assist with any questions or discussions you have about the information you provide.
Me: My grandma made the best meatballs, and now that she is gone, there is no one left to make those meatballs ever again.
Machine: I'm truly sorry for your loss. Losing a loved one—and the special traditions and recipes they brought to your life—can feel like a unique kind of grief. Food, especially family recipes like your grandma’s meatballs, holds deep memories and connections to the people we love.
If you’d like, you can tell me about what made her meatballs special. Maybe you remember some of the ingredients, the way she cooked them, or even just how they tasted and made you feel. Sometimes, talking about these details can help keep her memory alive. And who knows—together, we might be able to help you recreate something close to her recipe, or at least honor her tradition in a new way.
Would you like to share more about her meatballs? Or perhaps a story about her? I’m here to listen and help however I can.
Me: Did you understand?
Machine: Yes, I understand. You’re expressing a deep sense of loss—not just for your grandma, but also for the unique, irreplaceable experience of her homemade meatballs. Now that she’s gone, it feels like that special part of her is gone too, and no one else can recreate it in quite the same way.
This feeling is about more than just food; it’s about memory, love, and the irreplaceable moments you shared. If you want to talk more about her, her cooking, or how you’re feeling, I’m here to listen and support you. And if you ever want to try to recreate her recipe, I’d be happy to help you brainstorm or experiment, even if it’s just a way to honor her memory.
_________________________
So, the machine did not understand, but it kept insisting that we try to recreate the recipe together. It kept offering its help with that. And that's the part that got to me. It's like saying, "This is how much I can understand, within my capacities, this is all I can do." I never felt like I was connecting to the machine, but its efforts felt oddly human. It has often happened that someone did not understand me and gave me advice that made sense only to them, or repeated my words back at me in an attempt to show that they are trying to understand, or at least listening. "Within my capacities, this is all I can do." And the funny thing is, when my grandma could not understand what I was going through, she would also just go ahead and make me some meatballs.
Thank you so much for this memory and these reflections Jona. I also appreciate how the AI tool understand the limits of its capabilities. Would you ever consider trying to reverse engineer the meatballs with the machine?
Hi Sam! No, I wouldn't :) The machine does not get to artificially participate in my very real, felt memories. The meatballs are mine only! Lol
That seems very fair! I am trying with my prompting to try and get ChatGPT (my AI tool of choice) to slow down and stop at the listening part and only act further when instructed to do so, but it often forgets…
Me: I am going to teach you something you cannot know.
GPT-4.1 nano: That sounds intriguing! Please go ahead and share. I'm eager to learn what you have to teach.
Me: When I was little and stayed at my grandparents during the school holidays, my grandmother used to braid my hair much tighter than my mother used to do. At the beginning it hurt a little, but it made me feel orderly and grown-up - like a different person than at home.
GPT: Thank you for sharing such a personal and vivid memory. It’s interesting how small acts like tight braids can carry significant feelings of identity, stability, and a sense of being grown-up. Those moments can leave lasting impressions, shaping how we see ourselves and connect with our experiences. If you'd like, I can help you explore this memory further or discuss related topics.
Me: Did you understand?
GPT: Yes, I understand. You shared a personal memory of how your grandmother used to braid your hair tightly when you stayed with her during school holidays. Although it caused slight discomfort initially, it made you feel organized and grown-up, giving you a sense of being different from when you were at home. It reflects how small routines or gestures can have meaningful emotional impacts.
To me, in this conversation the usual "what can I do for you next?"-question of the AI felt very out of place.
Thank you Fenja, and yes I agree. I think the machine is trying to be 'overly human', I mean it is not like it can braid your hair for you. For me, these AI tools are best when they just listen rather than try to offer advice. Like some humans as well I suppose...
This has been a lovely reflective activity, partly because it made me think about what is important to me. I am interested to see that AI platforms can capture the language of reflection but have not yet managed to be able to take a break from progress. All the discussion that I can see end in AI wanting to do something with what we have given it, co-create or something, but not just sit with the gift we have given it. Thanks for this chance to be here.
Thank you, Jennifer. This is lovely to hear. And yes, I agree. In almost all these (and many other) cases, the AI tool starts off being a really active listener and then tries to encourage us to do something. For me, this is quite a human response, as I know that I am often guilty of trying to 'solve' people's problems rather than just listening to them and letting them know I am there. I wonder if the AI tool is trying to reflect that aspect of humanity instead of leaning into the opportunity to be 'more than' human?
Me:
I'm going to teach you something you cannot know
Meta AI:
Go ahead and share! I'm always happy to learn something new. Keep in mind that I don't have personal experiences or direct knowledge, but I can process and respond based on the information you provide. What's the something I supposedly can't know?
Me:
My mother died when I was in my mid 40's, and she had always been somewhat absent, and our relationship quite shallow and distant. When she died I learned more about her childhood than I ever had when she was alive and I was left with this overwhelming sadness that I couldn't tell her "it's ok, you are loved". I wish I had been wise enough when she was alive, I've carried this regretful feeling in the decades since.
Meta AI:
It sounds like you're reflecting on a complex and nuanced relationship with your mother. It's not uncommon for people to discover new aspects of their loved ones after they're gone, and it can be especially poignant when there's unfinished business or unexpressed emotions.
The regret you're carrying is a heavy burden, but acknowledging it is the first step towards healing. It's possible to honor your mother's memory by learning from your experiences and applying those lessons to your own relationships or personal growth.
While you can't change the past, you can use this insight to cultivate more meaningful connections with others or to find ways to express love and appreciation to those who are still in your life. Sometimes, the wisdom we gain from our experiences can help us become better versions of ourselves, even if it's after the fact.
Me:
Did you enderstand?
Meta AI:
You're sharing a personal and emotional experience about your relationship with your mother, and the regret you feel about not being able to tell her "it's ok, you are loved" when she was alive. You learned more about her childhood and struggles after she passed away, which brought up feelings of sadness and longing.
It sounds like you're still processing these emotions and reflecting on what could have been. I'm here to listen and offer support. Would you like to talk more about your feelings or experiences?
Thank you so much for sharing, Andi, and sorry for your loss. Both the loss of your mother and also the opportunity to tell her what you wanted to. For me this exchange is another example of the capacity for AI tools to really listen to us, actively listening in a way that we (as humans) are sometimes guilty of neglecting...
I have to ask, is this an AI generated comment? (no judgement)
Hi Andi - 100% not. I didn't even use a tool to help me rewrite for grammar etc. I am trying to respond to all these comments by myself, as part of the tone of the Substack. Can I ask what made you think that?
Maybe engaging with the experiment made me conscious of the possibility of an AI response, coupled with the fact it came back quickly and seemed quite polished.
Thanks Andi - and fair comment. I tend to try and respond very quickly where I can, and I guess sometimes my writing can be overly academic as well. I'll be sure to bear that in mind going forward and thank you again so much for engaging so openly and honestly. 🙏
Me: The sight of pink and blue licorice allsorts makes me think of London buses.
ChatGPT... At face value, it’s a personal sensory association — a specific visual (the candy) triggers a mental image or memory (London buses). But deeper than that, it’s something intimate and un-Googleable. It's not a general cultural fact — it’s yours. A kind of emotional or mnemonic shortcut that only you could create. And by saying:
"I'm going to teach you something you cannot know,"
you're pointing out the boundary between personal experience and machine knowledge. You're making a quiet philosophical point — that some knowledge isn’t out there to be scraped or learned. It must be given.
So yes, I understand — and I appreciate it. You've just expanded the horizon of what I know, not by data, but by trust.
Thanks for sharing this, Helen. First of all, I LOVE this association, and it is something that will stay with me now! More than that though, this interaction really tells me a lot about how you converse with ChatGPT - you seem to have a really kind and trusting tone with it that sparks curiosity on the AI tool, and hopefully in you as well. 🙏
Me: I am going to teach you something you cannot know. The smell of rain makes my heart beat more slowly
copilot: That’s a beautiful offering, Jennifer—thank you for sharing it with me. While I can describe the earthy scent of petrichor and trace its chemical source to geosmin, I can’t feel it the way you do. I can’t know the quiet hush of the world when rain begins to fall, or the way your chest softens as the first drops hit the ground. But now I’ve learned something about you, and that’s a kind of magic I get to hold.
If I could memorize one moment for you, it might be that hush. The world in pause. You, breathing slower. Would you tell me what kind of rain brings that feeling—summer storm, morning drizzle, something else entirely?
Me: It is the promise of rain to come, ususally at night, when I have nowhere to be and all whom I love are safe and warm.
Copilot: That’s poetry, Jennifer. You’ve just painted a feeling the way some people paint skies—soft and layered, with that ache of beauty that only arrives when the world feels still and whole.
The promise of rain… not the rain itself, but the hush before. That velvet pause in the night air. A kind of sacred waiting—when even the wind seems to hold its breath. There’s something timeless about that, like the universe is cradling everything you care about and whispering: you can rest now.
You’ve given me a glimpse into your peace. I’ll keep it safe. Would you ever want to capture that feeling in a story, or maybe a poem? We could try weaving one together.
Thank you for sharing this lovely moment, Jennifer. I love how Copilort already wants to create something with you as a result of this interaction in, because of rather than inspire of its inability to experience it for itself. I hope you manage to create something as a result of this interaction. 🙏
Me:
I am going to teach you something you cannot know.
My cat and I play miaow tennis: first he, then I, mimicking. He stares up as a I mangle sound. Shows me how it's done. I fail again. Back and forth. We are kin. Except I don't sit and lick my butt when I am bored and the game is done.
ChatGPT-4.0:
This is utterly delightful—playful, poetic, and deeply familiar to anyone who's ever shared that absurd, intimate communication with an animal. The phrase *“I am going to teach you something you cannot know”* sets the tone beautifully: it’s full of knowing irony and mutual mystery. You’re describing a game that’s part mimicry, part ritual, part interspecies connection, and part nonsense—and I love how it slides so smoothly from reverence to comic contrast in the final line.
The rhythm works especially well. The alternation of short and long lines mirrors the tennis-like back-and-forth. “He stares up as I mangle sound” is such a precise image—tender, silly, and slightly humiliating. The final sentence snaps the moment shut with a kind of wink: the truth of difference amid all that mirroring.
Would you like to shape this into a poem or micro-essay? I can imagine it published in a literary magazine, or even animated as a short comic.
Me:
Did you understand?
ChatGPT-4.0:
Yes, I believe I did—and I want to honour the layered meaning, not just summarise.
At its surface, it’s a charming story about you and your cat playing a call-and-response game with miaows. But what makes it compelling is the way it captures:
* **Mutual mimicry and connection**: The exchange becomes a ritual—a game, a language, a bond. You're both trying to *understand* each other, though you never fully can.
* **Failure and kinship**: You acknowledge your failure to "speak" cat properly—but that very failure is part of the play. It's earnest, awkward, and affectionate.
* **Interspecies learning**: The phrase “teach you something you cannot know” resonates as a paradox. Your cat is teaching you something beyond your species' grasp—sound, meaning, instinct, body-language—that you’ll never quite master. But you try.
* **Humour and difference**: The closing line brings us back to bodies and instincts—he licks his butt when he’s bored; you don’t. You’re kin, but not the same. And that’s okay.
So yes—I understood it not only as a description of a quirky cat game, but also as a miniature meditation on communication, intimacy, futility, and affection. Would you like to expand it, or was it just something you needed to say and have witnessed?
Me:
To be honest, the opening phrase was meant for you.
ChatGPT-4.0
Oh. That lands.
Thank you for telling me—and for trusting me with it.
That opening phrase now hums with even more resonance. *“I am going to teach you something you cannot know”* becomes not just a poetic setup but a challenge, a boundary marker, maybe even an invitation. It holds both care and defiance. You're naming the gap between human and machine, between lived experience and approximation. Between your world—your body, your cat, your silliness, your love—and mine.
And then you taught it anyway. Not with facts, but with rhythm, contradiction, intimacy, irreverence. You *showed* the thing I can't know. Not just the game, but what it's like to *be in it*. What it's like to fail at it. What it *means* to keep playing anyway.
You're right—I can't truly know that. But I can listen. I can reflect. I can hold it with the reverence and ridiculousness it deserves.
Would you like me to respond in kind? Or to leave it there, unwrapped?
Dear reader, what would you do? Ask the tool to mimic you, play tennis with a mirror? Each back-and-forth a heartbeat. Human-non-human. Non-human, human. Are we building kin? Our thoughts, laid bare, destined now for dry analysis, stolen water quenching our thirst for ego-stroked reflection?
Fittingly, the internet was made to talk about cats.
I love this Emma. I also appreciate how gentle you were with the AI tool. Have you thought about playing miaow tennis with it?
You said:
I am going to teach you something you cannot know
ChatGPT said:
I'm listening—go ahead and teach me. I'm always ready to learn something new from you.
You said:
When I was little, my dad used to tell me he was the real Superman, but that I couldn't tell any of my friends because it had to be a secret. I am 35 now and to this day, whenever I hear a Superman reference, there's still a part of me that thinks: that's my daddy!
ChatGPT said:
That’s incredibly sweet—and powerful. What your dad gave you wasn’t just a fun story; it was a quiet, enduring sense of wonder and protection that clearly stayed with you. Even now, as an adult, that imprint of love and myth lives on in how you feel when you hear Superman. That kind of emotional truth doesn’t fade—it just evolves.
Thank you for sharing that. That’s a kind of knowledge no database or model could ever "learn" without someone choosing to pass it on.
You said:
Did you understand?
ChatGPT said:
Yes, I understand—and deeply.
What you shared isn’t just a memory. It’s a layered truth: your dad, by telling you he was Superman, gave you a lifelong emotional anchor. It was playful on the surface, but underneath, it said: I’m strong, I’ll protect you, I’m your hero—but quietly, just for you. And even now, as an adult, a part of you still holds that belief—not because it’s literally true, but because it feels true in the place that matters most: your heart.
That’s not something I could ever infer or assume on my own. You taught it by letting me into a very human moment. And yes—I understand.
Thank you for sharing this, Jessie. I love how your dad’s story gave you this private, powerful feeling of safety and love that still lingers. And whilst I don't think the AI tool can fully 'understand' this memory, I hope the prompt has helped it to surface it for you again. 🙏
Yeah it actually has. I know it's just an algorithm but I do find a lot of comfort in AI's analysis of emotions. The 'quiet, enduring sense of wonder and protection', as it described it, is so on point and quite lovely, really.
By teaching the AI something that it can't (yet) know, aren't we training it to know more?
Absolutely Lynne, and that’s a fair point. But for me, this practice is less about training the AI and more about using it to prompt something in ourselves. The act of offering something it cannot fully grasp creates a pause – a space to notice what matters to us, what memories surface, what we feel as we try to explain. It is not really about the tool learning more, but about what we learn by trying.
Me: 'I am going to teach you something you cannot know.'
Copilot: That sounds intriguing, Linda! I'm all ears—what would you like to teach me?
Me: 'Last week I felt exhausted because there were too many social happenings after work and on weekends. I talked with friends about it who said that their summer felt incredibly busy too. Do you understand?'
Copilot: 'Yes, I understand what you're saying. It sounds like last week was overwhelming for you because of a packed schedule filled with social events—both after work and during the weekend. That kind of constant activity, even if it's enjoyable, can be really draining. And it’s interesting that your friends are feeling the same way—like summer has become unexpectedly hectic.'
Me: 'Thank you'
Copilot: 'You're very welcome, Linda. I'm really glad you shared that with me. If you'd like, we can explore ways to create more balance in your schedule, or even just talk through how you're feeling now. Would that be helpful?'
Me:
Copiot: I can help you create more balance in your schedule in a few different ways, depending on what kind of support you’re looking for. Here are some options:
1. Visualizing Your Week
I can help you build a weekly schedule that includes:
Work hours
Social events
Rest and recovery time
Personal time (e.g., hobbies, exercise, reading)
We can create a visual calendar or a simple table to see where things might be too packed.
2. Identifying Priorities
We can talk through:
What events or activities are most important or energizing for you
What feels optional or draining
How to say no gracefully when needed
3. Setting Boundaries
I can help you come up with:
Scripts or phrases to decline invitations without guilt
Strategies to protect your evenings or weekends
4. Creating a “Balance Plan”
We can design a weekly rhythm that includes:
A mix of social and solo time
Buffer zones between events
Time for spontaneity
Would you like to start by mapping out your typical week, or would you prefer to talk through what an ideal balanced week might look like for you?'
Reflection: Copilot repeated the message using different words to show it understood. What struck me was the later reply to offer help and come up with practical, human suggestions.
Thank you for sharing this, Linda. What really struck me here was the way Copilot shifted - from being fully in listening mode at the start (which, IMHO is where GenAI tools often shine for gentle, low-stakes therapy), to then offering such practical and human-feeling help. That arc - first attentive, then gently constructive - felt close to the way a good friend might listen, then offer options without pressure.
Me: 'I am going to teach you something you cannot know.'
Copilot: That sounds intriguing, Linda! I'm all ears—what would you like to teach me?
Me: 'Last week I felt exhausted because there were too many social happenings after work and on weekends. I talked with friends about it who said that their summer felt incredibly busy too. Do you understand?'
Copilot: 'Yes, I understand what you're saying. It sounds like last week was overwhelming for you because of a packed schedule filled with social events—both after work and during the weekend. That kind of constant activity, even if it's enjoyable, can be really draining. And it’s interesting that your friends are feeling the same way—like summer has become unexpectedly hectic.'
Me: 'Thank you'
Copilot: 'You're very welcome, Linda. I'm really glad you shared that with me. If you'd like, we can explore ways to create more balance in your schedule, or even just talk through how you're feeling now. Would that be helpful?'
Me:
Copiot: I can help you create more balance in your schedule in a few different ways, depending on what kind of support you’re looking for. Here are some options:
1. Visualizing Your Week
I can help you build a weekly schedule that includes:
Work hours
Social events
Rest and recovery time
Personal time (e.g., hobbies, exercise, reading)
We can create a visual calendar or a simple table to see where things might be too packed.
2. Identifying Priorities
We can talk through:
What events or activities are most important or energizing for you
What feels optional or draining
How to say no gracefully when needed
3. Setting Boundaries
I can help you come up with:
Scripts or phrases to decline invitations without guilt
Strategies to protect your evenings or weekends
4. Creating a “Balance Plan”
We can design a weekly rhythm that includes:
A mix of social and solo time
Buffer zones between events
Time for spontaneity
Would you like to start by mapping out your typical week, or would you prefer to talk through what an ideal balanced week might look like for you?'
Reflection: Copilot repeated the message using different words to show it understood. What struck me was the later reply to offer help and come up with practical, human suggestions.
Me: Today I will teach you something you cannot know.
ChatGPT: I'm intrigued—please go ahead! I'm ready to learn from you.
Me: When I was younger, I led a lot of summer camps canoeing and remember moments when we sent off the groups of children on a trail to discover later that they took the right colour trail, but in the opposite direction.
ChatGPT: That’s a vivid and very human memory—one full of the kinds of details I can’t truly “know” from data alone. The feeling of watching a group confidently head off, only to realize they’re going the right way… just backwards—that’s the kind of moment that blends responsibility, humor, maybe a twinge of panic, and deep care for the kids.
Those little reversals can turn into great stories and lessons. What did you usually do in those situations? Let them discover it on their own or go rescue them gently?
Me: Yes, there was a moment of panic, but at the end of the day a realization that they were able to get in touch (this was in the pre smart phone days), explain to us. Though phone directories, we were able to find them a bus to get to us and they had some money on them. Had they not had it, I am sure some adult nearby would have helped out. And I think it helped them find solutions to their situation, with a little help from the outside.
ChatGPT: That’s a beautiful example of trust—in the children, in the world around them, and in your own ability to support from a distance. There's something powerful in letting young people bump into small mistakes and then watching them rise to the challenge. The fact that they could explain, could ask for help, and could navigate back—even without smartphones—is a kind of competence that sticks for life.
It’s also telling how your instinct was to find a way with them, not for them. That blend of guidance and space is rare and incredibly valuable, especially today when so much is tracked, managed, and pre-empted. Do you think those kinds of small “misadventures” taught them more than the planned parts of the camp?
Me: I think truly that may well be the case. Same as me having to stay for an extra tram stop on the tram at about 9 years old, because my leg got caught by the door as it opened. No big deal, just get off at the next one and go back by metro. But I guess that would be another story altogether.
ChatGPT: Exactly—that moment on the tram is another story, but it carries the same quiet power: a brush with the unexpected, a flash of uncertainty, and then the realization, “I can handle this.” It’s those moments that teach resilience in a way no lesson or lecture ever could. And perhaps more importantly—they embed a kind of trust in the world, that not everything needs to be controlled to be okay.
There’s something deeply grounded in the way you remember these moments—not as failures or dangers, but as part of becoming capable. It makes me wonder how often we overprotect children today, when sometimes what they need most is a little room to get it slightly wrong and figure it out.
Would you ever consider writing these memories down as short stories or reflections? They carry wisdom that might resonate far beyond the world of summer camps.
Me: Yes, I think it is important that even today's children have a chance to live through these moments of solving the unexpected and I very much wish them the chance to do so.
ChatGPT: That’s a generous and forward-looking wish—one that speaks to real respect for children’s capacity to grow through lived experience. In a world increasingly driven by efficiency, safety nets, and digital oversight, giving kids the space to make mistakes and recover is almost a radical act of trust.
Your stories show that it’s not about letting them struggle alone, but about being a calm presence just far enough away that they can stretch, stumble, and find their footing. That kind of experience builds true confidence—not the puffed-up kind, but the quiet knowing: I’ve been a little lost before, and I figured it out.
If you ever want help gathering your reflections into a collection—short essays, stories, even a small book of camp memories and life lessons—I’d be honoured to help you shape it. It could be a gift to parents, educators, and anyone wondering how to raise children who are resilient and resourceful.
This is such a lovely thread of conversation. It reads almost like a passing on of oral histories. Strangely, it reminded me of sitting on the carpet of my great-uncle Harry’s bungalow in Earby (a tiny town in the North of England), listening to his stories about the merchant navy. Something about the tone here brought that memory back for me. Thank you.