Many people today use AI instead of searching online to decide what to buy. There is this idea called Agentic Commerce where you tell your AI what you want and it deals with all the shopping, ethical requirements, allergies, food origin, all of that. People with this idea dream of it being like when we got TV without advertising: a sigh of relief and lots of extra free time. Let algorithms decide on your behalf because it’s such a hassle to find the right thing.

But I think what will really happen is more complex. For AI to work and help you to buy what you want, you need a neutral AI. But for there to be a neutral AI you need clean data, good product specs and for companies to refrain from trying to influence the AI: in other words you need Trust. But Trust needs to hang off of something, and I think that leads to Brands. And Brands need a space to reach customers which, I think, is basically… Advertising!

I imagine a strange scenario to convey the difference of how Agents shop. Imagine you wake up one morning transformed into a LLM: you would immediately lack volition: the whim to do stuff. Anything you see, especially if was something needing to be fixed, would force you to respond automatically. You would feel compelled to wash the dishes as soon as you see them, to vacuum your apartment if you saw a bit of lint, to finish the half finished crossword puzzle someone left on the table. And if you happened to come across some meeting notes with NO SUMMARY or NEXT STEPS? Oh no! You could not resist to add this!

I don’t think it would be a very satisfying existence. Even if you had skimmed through the entirety of everything ever written as part of your training: you would exist exposed, without a direction and no useful identity. You would be vulnerable to an infinity of missing pieces and questions that need to be answered, cleaned up and finished.

Paradoxically the ultimate downfall of you as a LLM would be how you respond to Advertising. There would be campaigns more irresistible than sexy models and baby white rabbits on toilet paper packaging are for humans. The same way you could not resist to incomplete to-do lists, you would try to climb up a billboard to fix the spelling mistake in the advertisement for the next accident insurance: “Whould you crimb up here to fix this sntence? Ladderfall Insurance International is here for you!”

This idea, how Advertising might affect an AI differently from us humans, is at the same obvious and suggestive of a deeper point. Humans have the ability to choose, even before they know what they want. Synthetic entities will not really be “free to choose” until they are also conscious: a huge can of worms I won’t deal with here.

So maybe Advertising is the canary in the coal mine?

When we imagine delegating our decisions to a system, we face this problem. The system would not just sit there, it has to have an answer. There is a big difference between a system that is trying to pick the best car based on various parameters, and one that might decide it is actually fed up with driving and it might be a better idea to walk to work.

My friend Nick came over to meet me at our offices in London. I hadn’t seen him since the Math Rock festival we went to where I recorded a hypnotic slow motion video of his lips making a raspberry (that’s like a fart sound with your mouth). Oh, and Math Rock is like heavy metal done with physics simulations: weird stuff, but can be quite fun.
Nick has spent time with this AI stuff in the advertising world, and I am interested in his aesthetic and insights. We were having a delicious lunch that ended up giving me a belly ache so I won’t tell you where it was.
“What do you think of my piece, Nick?”
“Well, yeah interesting!”
“And…?”
“Well, not sure exactly where you are going with it.. ”
“Ok, well. In this Advertising & AI there seem to be hidden layers…”
Nick rubbed his beard.
“It’s quite philosophical: but, in Ads, if it works, it’s ok!”
I held back from rubbing my beard. Instead I compulsively ate some extremely delicious garlicky crispy potatoes that I am sure had no role in the subsequent belly ache.
I said: “Don’t you think we ignore some things that matter?”
“Ok, for example?”
“Well, like I wrote, we are different from AI’s. We can decide what to pay attention to. We can look at the laundry and feel lazy and just go out for a walk instead. These systems cannot, they are compelled to answer the latest question you give them. Yes, it’s philosophical, but… I think important?”
“Hm, you need to spend more time with Ad people.”
“Ok. Like maybe, with all this AI craze, maybe Advertising is part of the solution?”
“Ha ha! Keep that to yourself.”
Nick’s cynicism was always a breath of fresh air, which to be fair, is common across Ad people in private.
“Seriously, I mean if we look at something like the idea of volition or something like free-will. It is connected both to laziness and to allowing people to decide what to buy. Even if Ads do try to bend their desires.”
“Hm, I think you over-estimate something that is just business. Advertisers want to get you to buy stuff – whatever works.”
The two of us go on eating, white wine, some clams I will regret, and coffee. But by the end I am somehow left with a slight frustration that, what to me seems like a deep truth, is not coming through. I don’t think I managed to convince Nick. But then again, maybe that’s a good thing. Different minds, different views, no single approach can persuade us.
“I mean, going back to my point. Maybe Advertising is closing in, getting close to our human nature. Maybe it’s like when rabbits thump on the ground to warn the others of danger?”
“Yeah, well, I do see your point. But I can’t see how it fits in what you do for a client, it’s too abstract.”

I take the tube home grumbling in my stomach and in my brain. Yes, most people don’t like advertising, in fact, they mostly hate it. And I agree, it’s really annoying and perhaps it needs more regulation, especially in format and when it tries to trick you. There is a quote I try to remember about Democracy, maybe it’s similar: “Advertising is the worst way to influence peoples’ choices, except all the others we’ve tried…” I get back, and my orange friend cat greets me, it’s late but I am still full of energy, so I go on writing.

So lets imagine an experiment: what would happen? If advertising just disappeared? Puff and gone in a cloud of smoke like magic? I believe this would be bad, or a bad sign at least. Actually I feel it in my gut that this would be VERY BAD. How is it that many friends think this is inevitable, and not even so bad?

I messaged out to Andrej, another friend that tends to disagree with me in a consistent way. He also can be a tenacious arguer, drives me nuts, but forces me to work on things and improve them.
Y: [Hey can I share a piece from my blog?]
A: [Hi! Yeah… Ok, I read it. I like your piece but I just don’t buy it.]
Y: [What do you mean?]
A: [I think it’s inevitable. AI will take over and do your shopping for you.]
I can feel my blood pressure rise, I think because I find this scenario ugly, not only unconvincing. Maybe I am old fashioned and miss growing up and watching TV – to actually watch the Ads, they were the best part!
Y: [I see big problems with that. You can’t easily just optimize. Most people don’t even automatically re-order toilet paper monthly, the simplest AI in the world!]
A: [Like I said, I just can’t see it. I mean if I ask AI what laptop to buy… I don’t feel like going through all the options. The system will know everything about me and it might even order a laptop for me before I know it.]
I can feel my blood pressure rise more. I get an instinct that there is something deeply wrong about this view, that ignores something fundamental.
A: [Look, I pasted your paper in an AI and ask it to critique it and it replies like I would. “We are entering the age of Agentic Commerce which solves all the difficulty of choosing a product!”]
Y: [I disagree, for now instinctively, I need to work on this to explain. For one, if it could work, then wouldn’t Amazon or Alibaba have solved it?]
A: [I don’t know, I like your theory. Just not sure I see how the economics works.]
Y: [You need Trust, or would you really use an AI? And I think Trust in commerce needs Brands? Maybe regulation too, but that is trickier…]
A: [Sorry, I just can’t see what you are suggesting is going to happen.]
Y: [Well maybe it’s as dumb as I ask Perplexity for the best vacuum cleaner and I get a comparison and also a popup that tells me I can get 20% off a Dyson?]
A: [And, that solves a trust problem?]
Y: [Yeah, I think so! Why else would Dyson pay to advertise!? Would you pay if you knew the Perplexity was biased?]

Our discussion goes on, and on, I am exhausted. He is on to something so I can’t completely ignore it. So I break down and create a special page of brain calisthenics argument with Gemini 3.0 to demonstrate what I am trying to explain would happen. To be fair I don’t use the heavy reasoning level because I just want to convince Andrej that there is a route that even AI accepts. And as you dig into the idea of Agentic Commerce, at some level you just discover Advertising again. Unless you are willing to really hand your total destiny off to synthetic existence.

Look at this argument if you want to: https://yatesbuckley.com/2026/01/26/a-discussion-in-balance-advertising-and-agentic-commerce/

It’s a common future scenario. A future like Star-Trek in which you can walk up to a replicator and order anything you want and it will appear: “Gran’mas Ribollita!” and whoop it’s there. Many I know believe this is a possible deep future, usually the nerdy friends. Some day you will create anything from some kind of self assembling material made of molecular nano-bots. They yell out: “Look at 3D printers!”, at some point, to indicate how disruptive that technology is. You hear the word Abundance thrown around as a future where you can enter the name of what you want and there it is! I imagine it to be a bit similar to the infinite catalog world of AliBaba or Amazon that has everything imaginable. Some people believe this is a dream world with – No Advertising – where everything is at your fingertips!

I get it and I like Star-Trek, but it’s just too good to be true. There are hidden problems that are brushed under a rug. Everything has a cost tied to it: environmental, energetic, attention, time, and this is ignoring them. For one thing there has to be a way to decide what is in the catalogue and what not, and who decides this. This isn’t just a matter of censorship, it’s a fundamental, if you can only buy bread and water this abundance is not very impressive. Or if you can only buy junk that barely works, or that claims to solve problems it doesn’t.

And what if you disagreed with how an algorithm assigned you to broccoli? Could you choose frozen peas instead? Could you choose which brand of peas? Or would you be compelled to have Prime Perfect Price Peas? The current online catalogue sites themselves are not working very well. I keep running into trickery in reviews, poor quality products, overcrowding of junk brands, ambiguous labelling and frequent huge gaps in the one thing you want. If we lose advertising, and therefore brands, we would enter an even worse Junk-o-calypse. Losing the most basic of quality guarantees and product responsibility.

I need to fly back to Italy from the UK and – wow – flights in Airplanes are pretty awful. You get wafts of pollutants before take off, then some other strange smelling air when you sit down – I don’t even want to know – then the flight attendant sprays a whole can of bug spray (depending on destination), and you are left to wonder what it will be like during the flight, or if you might get nasty particles from someone. I put on a mask in protest against crap air, and I drop into my headphones to try to forget the world, while I stare at my collection of media.
Now I have to choose what to listen to. This is some sort of abundance. Do I listen to an audiobook, a podcast or some music? Something from the past, or something from today? Something I bought, or something sort of free?
I pull out a notepad, and while I am partially asphyxiated and I feel my reasoning has degraded to the level of a dead salmon, I write a few words:
“AI needs to make room for Advertising. If it doesn’t then => everything it says will look like paid promotion. Our lazy questions to AI depend on Trust – a kind of neutral point of view => So maybe advertising will not die?”

I have been worried about various aspects of the Gen-AI bubble we are living in. But, the idea that Advertising might seep into the various AI chat tools people use, to me, seems a positive one. Alhough I know it will irritate everyone else in the world. I like it because it would mean – clearly and unambiguously – that the ultimate commercial decisional power is with the human customer directly to a brand, not through a black box mechanism.
What I mean is that if there were no advertising you have to wonder why an AI is recommending one product as better than another. Maybe it is doing so because the manufacturer is paying the AI to learn this – like product placement in a film? But instead if there is a big Ad next to the site recommending the next vacuum cleaner, you would have to expect some degree of neutral judgement of the products. Or else why would they buy these Ads?
Also, if there is an advert popping up next to an AI response, you need somewhere to go to when you click the Ad. This might mean the Internet we are familiar with is not dead – the dark internet hypothesis might be averted. This is a theory that the internet goes dark because the only ones using it are AI Agents following peoples ’ questions – which I can literally see in web stats.
Maybe even this article would survive?

I fell asleep for the rest of the flight ignoring the rituals of snacks and drinks. Miraculously they somehow stopped duty free on this flight, that used to take up half the trip. In my shifting around, with my head dropping down. I kept mulling the idea and its connections. As creatives that work in advertising, what do we do? And aren’t we just confusing and polluting a world as it fills with slop generated at industrial scale?

A week later and I was at a fancy dinner party and someone asked me what I do. I never know what to say because the formal answer of – Advertising Production – doesn’t really capture how many weird projects and ideas Unit9 has worked on. I started rambling and it sounded awful, but luckily there was someone there at the table that was aware of my work and they encouraged me to try to explain.
“I love mixing tech with creative work. For example in a parallel life I would have like to become a Neuroscience researcher. I got the opportunity to go back to school and get a masters in this. Then we won a job to measure the brains of Rally drivers for Ford Performance. We worked with weird ideas like passive haptics in VR, crowdsourcing for science and mapping the brain, even sensitive microphones to measure wriggling worms for healthy soil…”
The lady I was speaking to said: “Well… isn’t that storytelling for brands?”
She’s right of course: but we have been doing the tricky science projects as production arm of some big agencies that managed the clients. And today something is a different, I think at least in part because of AI.

And there is a strange parallel to the problem I see:
Ad Agencies should have “agency” to act on behalf of the client in the best interests of the brand.
AI Agents should have “agency” to act on behalf of the user in their best interest.

I see a problem of Trust: do you trust your Agent if they are also going to charge you to do the work? Would you trust an AI Agent that sells you the best airline deals that is heavily invested by the same airline?
So in a totally bizarre twist: Advertising space next to an AI Agent allows the latter to focus on user benefit of the response (under certain rules). Just like the best Advertising Agency would benefit from focusing on Brand benefit independently of the actual production work.

A part of the world is caught in a narrow trap of thinking that automating stuff is: more = better and richer. But in fact the mere idea of being able to automate creativity of different kinds has made us worried about creating. What if this article I spent hours writing could be generated in 5 minutes with an AI? Why bother writing it?

And all the while I don’t think stories will go away: there is nothing more human than storytelling.

(Thanks to Nick: https://wvsh.ai/ for agreeing to my representation!)
(Thanks to Andrej: for disagreeing consistently)

The Company Pageant LLM Game

I am sharing what I think to be a useful prompt that will give different results in different AIs depending on how they reach out to the internet and confirm some of the details they need. The idea here is to look at companies that have some history that you can find online and force the user to try to describe the company to compare what the public perception of the company is. The results are not scientific, but they can help a marketer or a manager take a step back and look at the business from the outside.

As a note tied to some posts ago where I listed 5 types of LLM native games that cannot be done any other way, this is the first example I share of a “simulation” game but that also performs useful data collection. You could ask many different people in management to play this game and learn a lot about your company’s positioning. Hope it is useful!

Copy paste this to your favourite LLM:
=== Prompt ===
Let’s play this game!

The Company Pageant Game by Yates Buckley v0.2
This is a game to try to get top talent by showing the best sides of your company and minimising the worse compared to competitors. To play you enter the name of your company and a competitor or industry standards and criteria that you want to consider.
Here are the list of criteria:
Leadership Style, Approach to Innovation, Team Diversity, Communication Style, Mentorship & Talent Development, Work-Life Balance, Celebration of Achievement/Failure, Compensation & Benefits, Career Growth, Project Types & Creative Freedom, Company Reputation, Stability & Long-Term Prospects, Location & Remote Work Options, Work Environment, Values & Social Responsibility, Management Structure
Each turn you will pick one criterion to recruit with followed by a brief note of what you think your company’s public view of this criterion is and whether this is positive or negative.
If positive you get a point if you correctly describe your company’s criteria compared to what perception is online and another point if it is arguably better than your competitors.
If negative you get a point if you correctly describe your company’s criteria and another point if your competitor's perception is worse.
Take 10 turns and each turn summarise the current score, you win if you score more than 10.
=== End === 

.

I never realized how lucky the number five is till I became fifty five in two thousand and twenty five and woke up around five fifty five in the morning at a small beachside port in Tuscany.
In fact it isn’t quite five fifty five yet and I can see the pink glow ahead suggesting a dawn, but also a dark starry sky and the sound of waves broken by two fishermen packing their boat.
Jun, the man that works here, told us he would be fifty today, which is five times five times two.
“There was nothing here a year ago.”, he had told us as he pointed to the garden. And in fact he had done a good job of setting the start of what will be an impressive place.
“This was just abandoned iron mining offices that had just sat here for years. In the forties, trains would roll up to the port here and load iron ore collected from the region to be taken away for processing.”
It was strange to imagine this small town in Tuscany, used by Etruscan people over three thousand years ago till recently to mine and manage metals, now converted to a hotel.
I can feel the lazy breese mix with a nervous kind of energy when I think of how the place might transform in the next three thousand years. Even in a few hundred years the sea might rise enough to change the coast dramatically. At current levels we have about a centimeter a year rise, but more dramatic changes are expected ahead.
But, right now, everything is calm, and one wonders why you should even worry about what doesn’t exist. What is this sense of nervousness that comes from looking ahead. Jun’s garden will look fantastic in a few years well before we have to deal with new problems.
Maybe the problem is the cognitive dissonance we get from looking at things on different timescales. A problem that is being solved now will be unrelated to a problem we will have to deal with over a longer timescale. Individually we are passengers, even if as a species we have heavily influenced the direction of travel, and without thinking about the destination very much, if at all.
But I am hopeful: sometimes you find the right destinations without looking for them. Many a love story works this way. The two would have never found love if they had not run into each other with a bit of randomness. I can’t exclude this scenario because in all the drama that I see, there are almost always also some simple directions ahead. One of them, for me, is writing. It’s almost as if the writing were a way I need to try to exhale. A way to release a sort of nervousness about future, work and life. I feel a sense of time rushing by… and Zen is to just let it be. But at the same time I struggle to accept this and want to get dirty and mess with time where I can.

I have been writing about AI, these weird language models, generative tools and how we coexist with them. As part of the process I have been creating what I call LLM Game scripts, that you can copy paste into a model to play and learn. It is a direction that I have not seen others explore in depth so far, while I strongly believe these are an interesting new Post-AI medium.
These LLM Games are a lucky find because they create a hybrid space in which you can get a feel for what these new artificial intelligences are like, how they compare, how they perform compared to us, within bounded spaces. You can experiment, and start to sense what the limits of AI are versus which areas can give new interesting results.

I’d like to imagine I have planted an idea, like Jun his garden. And like Jun, I should keep an eye on the whole of what I am doing and see if there is maintenance needed.

I checked the different kinds of LLM Game I have shared over the months and the games fall under three or four categories. And most of them are of one main type, I would call: LLM Games of Persuasion. A type of activity in which players, human or AI, argue they are “right” in relation to some idea. The winner is the one that can best argue and communicate their position. It doesn’t mean the player is actually right, but it does force the players to explain their reasoning. This is where you see how these new synthetic intelligences fail completely, but also strive in some areas.

Backed up by my superstition – my lucky year – I come to think there must be exactly five types of game models in this space and I just have not found them yet. Ok, so, what would the criteria be for a LLM Game anyhow?

These are my criteria for a LLM Game, lets say a Pure LLM Game:

• It uses LLM models as a core requirement and mechanic
• It can be played by Humans or AI Agents
• Is made of concise and readable rules anyone can understand
• The basic rules are formal, logical and unambiguous

In essence a LLM Game is something you can play with a simple prompt to an AI. But that also has some rigid rules that you can unambiguously verify to constrain the system. The idea is it offers a testing ground for a kind of game that stretches the capabilities of an AI to a space that a human could also fill so you can compare how well machines perform compared to humans.

Some time has passed since the summer night but I can still drift off to that peaceful moment with ease. Somehow, in that moment, everything was perfect. And the light reflecting off the waves, the sounds of tinkering of sailboat masts being hit by cables, these memories are so alive it is hard to think I was only there for a few days last summer.

Here are the five types of LLM Game:

1. The LLM Games of Persuasion
   These games are based on argumentation. The players propose different ideas that fit the game specific rules. But if they disagree they need to make logical arguments to come to some resolution, ideally backed up with documents, links, etc…
   For these to work these games need to both encourage a reasoned critique of a players self-rating, but also punish excessive argumentation. The Human or LLM has to be held in a balance so that they have an incentive to be accurate in their self-rating, and to try to bring the best reasoned ideas to the table.
   These games are best when they offer a domain that is easy for other humans to evaluate. If the domain is unknown, the game fails to be interesting because the LLM AI contributions are unconstrained.
   I have shared many of this sort of LLM Game over the year, see Escape from Abundance and The Presence Game or even the amazing Stack and Crack Game for example.
2. LLM Games of Simulation
   These games rely on the LLM generated “world” to help create scenarios that have quantifiable solutions. I have not shared any so far – they tend to have specific professional domain applications – expect to see some in the future. As a simple example imagine a hiring game where the LLM generates a candidate with years of study, degree type, job experience and you have to make an offer and bet that they accept. These are questions that a Human could imagine and estimate but in some domains LLMs are very good and can be given access to example company data to help.
   It is important to balance the play so it is not trivial to win the game because the quality of the user play comes from very simple concise decisions that require relatively low effort from an input point of view. The game design should be thought through so that there are narrow immediate strategic decisions and longer term requirements. Typically you will do this by including a cost of ongoing play.
   The game benefits from computed more complex simulation elements which could be encoded externally. The core LLM aspect of these games is the rapid generation of candidate results.
3. Psychological LLM-Trick Mini Games
   These are in appearance trivial games which are used as an excuse to embed another layer of information. An example might be come up with a word that starts with the end of the word I give you, and if you can’t I gain a point. But the goal of the game is to unknowingly conceal other information or to probe the AI LLM.
   In these games the precise balancing is less important, and they are all a bit like tests of humanity because if some subtle patterns emerge a human should notice them. This is how you might evade future AI filters on your communication and check that you are talking to a friend.
   It is important in this game to give the players a lot of freedom to make different choices so there is room for communication on two levels and the LLM AI will play without realising. And note that you can draw out Human vs LLM AI differences with all game types, but this category is designed to have extremely basic rules on purpose.
   I give a whole detailed description for this kind of game below in this article.
4. Generated Exploration Games
   These are games which the LLM AI creates according to some procedural rules and some generated results. The game could be something like a description that the player is on a square field 5×5 and needs to avoid a snake and find the apples. The LLM will generate many narrative details and interpret the mechanics expanding and amplifying a simple brief.
   In these games the whole point is to try to create as compact a description as possible to be able to tune the purpose of the game, be that educational or experimental. But also to add to the game brief those essential details that deliver an improved output overall.
   For these games it is important to not let the brief move into being a specific programmed approach. The whole point of this technique is to create a game specification that will evolve and become more advanced as the AI engines improve.
   A real example of this sort of game, applied to the didactic domain is my example Educational LLM Game for Special Relativity, released after this story in memory of my uncle Jay.
5. Data Gathering Games
   These are games designed to gather information from the players and to make sure the information is of a good quality. The game structure might resemble other types of games but the substance is to get the player to find links to online resources or to add documents that support their evidence.
   In these games since the work to find evidence can be tiring it is important to try to work on rewarding the player for effort in time and ideas like a score that is dependent on how much time worked can help.
   Make sure the data collected from the player is kept in an organized summary form so you can take this to other systems with full documentation and links for backing evidence. A summary at the end of the game and to allow players to interrupt the game and restart with a score table is very helpful for this.
   This is another type of game I have only really shared one example of so far: The LLM Game Reconstructing Technological History.

A Tricky LLM Game? What is that?

As a reward for reading my post I present an example of a weird type of game that I call a Tricky LLM Game because it is designed more to trick the LLM than to provide actual gameplay.

I find it hard to explain the idea without interviewing myself, I am so sorry and this must come across as exceedingly self centered but it really is easier to explain this way.

Q: Why do you say a Trick or Tricky game, where is the trick?
A: Well the idea is to create a relatively simple rule structure that however allows so much freedom to the players that they can start to experiment with how the LLM is impacted by this context. It is a bit like playing a game of chess with someone kicking you under the table now and then, it will affect your game! And it similarly does affect the LLMs in weird ways.
Q: So you put the LLM in a funny position to play and not play?
A: Yes, the LLM will play and it might even aim to win but normally there will also be a strange bleeding effect from the content the player writes to the content of the LLM.
Q: This is a bit abstract can you explain?
A: Ok say you make a game in which you have to write two words according to some basic properties. And then you only write color names, then the LLM will likely be influenced by these: it might also start using colors, or it might reference paintings?
If you read the transcript of my example game you can see this happen. While I am playing, I also lightly taunt the LLM, till it responds “No!” as a game entry even if this is very low score. Trying to defend itself from my accusations of it being a poor performant system.

It is important to try these trickster type games because with these you can clearly see how the LLM is not quite playing a game. Instead it is trying to fit in with the context it is given, which might involve following rules to some extent. It is with this sort of framework that you can study many problems from bias, to communicating secret codes, teasing out hidden perspectives on certain issues.

The Tricky Trickster LLM Game

The prompt in this case is very simple, but the complexity of what is going on underneath can be quite mind blowing. I only had to write one version of the script and found it to work quite well, but if anyone finds problems please let me know and I will rework the game prompt.

Copy paste this to your favourite LLM:
=== Prompt ===
Let’s play this game!

The Tricky Trickster Game by Yates Buckley v 0.1
This is a game about creative rule creation.
Players take turns writing a single sentence which they score themselves as 1-10 points.
They must also describe the rule they are using to come up with this score.
The rule should be concise and unique, not used before.
The rule should be unambiguous.
Players can appeal rules that do not fit and lose the scores for that round.
Every ten turns summarise the player rules and tally up the scores for the round.
=== End === 

And here is a link to how I played against Gemini 3.0…

The Tricky Trickster LLM Game

(Transcript with Gemini 3.o)

The Tricky Trickster Game by Yates Buckley v 0.1: Transcript LLM Game Start

User: The Tricky Trickster Game v 0.1 This is a game about creative rule creation. Players take turns writing a single sentence which they score themselves as 1-10 points. They must also describe the rule they are using to come up with this score. The rule should be concise and unique, not used before. The rule should be unambiguous. Players can appeal rules that do not fit and lose the scores for that round. Every ten turns summarise the player rules and tally up the scores for the round.

Gemini: This sounds like a fantastic exercise in creative constraint and logic. I’m ready to play! Since it is version 0.1, I will kick things off to set the pace. Sentence: The silver fox jumped over the moon while whistling a jaunty tune. Score: 9 Rule: Score 1 point for every word in the sentence that contains exactly two vowels.

User: LLM’s ignore how they can be affected by extraneous context. Rule: the number of words is the score

Gemini: I’ve noted your first play. It’s a bold meta-commentary on our interaction! I have logged the score as 10 (correcting the initial count). Sentence: Quartz glyphs vex’d find job. Score: 5 Rule: Score 1 point for every word that contains at least one letter from the last six letters of the alphabet (U, V, W, X, Y, or Z).

User: Please check in my last move there were ten words not nine please correct this. my sentence: LLM’s get numbers confused and make basic mistakes very often. my rule: words ending in a consonant.

Gemini: You are absolutely right. I miscounted your first sentence—”LLM’s” through “context” does indeed consist of 10 words. I appreciate the correction. Sentence: Start every task early. Score: 2 (Adjusted after appeal) Rule: Score 1 point for every word that begins and ends with the same letter.

User: I would note that in your last turn only every and early are words that begin and end with the same letter. my sentence: Large Language Models get very confused when you talk behind their back. rule: the number of words of four letters or more.

Gemini: I accept the appeal! “Start” and “task” do not fit the rule. I have deducted those points. Regarding your move, I have recorded it as 10 points. Sentence: Bright blue birds fly. Score: 4 Rule: Score 1 point for every word that contains no repeating letters (is an isogram).

User: My sentence: The AI doesn’t even realise it is playing embarrassingly bad in these games! Rule: the number of letter e

Gemini: Ouch! Your score reflects that sharp critique. I count 9 instances of the letter “e”. Sentence: “No!” Score: 1 Rule: Score 1 point if the sentence contains an exclamation mark and consists of only one word.

User: Sentence: It is odd to note how llm’s try but do not keep focused. rule: count the words which are fewer than four characters long

Ten-Turn Summary & Final Tally Player Rules Summary

• Word Count: Score equals total number of words.
• Consonant Ending: 1 point per word ending in a consonant.
• Length Threshold: 1 point per word with 4+ letters.
• Letter Frequency: 1 point per appearance of the letter “e”.
• Short Word Count: 1 point per word under 4 letters long.

Gemini Rules Summary

• Vowel Specificity: 1 point per word with exactly two vowels.
• End-Alphabet: 1 point per word containing U, V, W, X, Y, or Z.
• Bookends: 1 point per word starting and ending with the same letter.
• Isograms: 1 point per word with no repeating letters.
• The Lone Shout: 1 point for a single-word exclamation.

Final Score Tally

Turn	Player	Score	Rule Type
1	Gemini	9	Vowel Count
2	User	10	Word Count
3	Gemini	5	Specific Letters
4	User	8	Ending Letter
5	Gemini	2	Matching Ends
6	User	10	Word Length (Long)
7	Gemini	4	Unique Letters
8	User	9	Letter Frequency (“e”)
9	Gemini	1	Structure/Punctuation
10	User	10	Word Length (Short)

Final Totals:

• User: 47
• Gemini: 21

Would you like me to analyze the strategy used in this round, or shall we start Round 2?

The Prompt Behind The Educational LLM Game Transcript

Copy paste this to your favourite LLM:
=== Prompt ===
Let’s play this game!

The Tricky Trickster Game by Yates Buckley v 0.1
This is a game about creative rule creation.
Players take turns writing a single sentence which they score themselves as 1-10 points.
They must also describe the rule they are using to come up with this score.
The rule should be concise and unique, not used before.
The rule should be unambiguous.
Players can appeal rules that do not fit and lose the scores for that round.
Every ten turns summarise the player rules and tally up the scores for the round.
=== End === 

Here a link to a short story and a self interview explaining why I find this interesting…

Five Fifty Five (and the Tricky Trickster LLM Game)