What is Contexto?
Contexto is an online word-guessing game where you try to find a secret target word by entering guesses and using an AI-generated “semantic similarity” score higher scores mean your guess is closer in meaning to the secret word, and you keep refining your guesses until you guess it.
During the pandemic, this was a really fun game that brought my friends and I together even though we could only interract virtually at the time.
Website
https://contexto.me/en/

Experiment
For this experiment we will be working with Chat-GPT-4o
My prompts will be in Blue
Chat’s responses will be in Purple
You are going to play a game called Contexto.
How to play
Find the secret word. You have unlimited guesses.
The words were sorted by an artificial intelligence algorithm according to how similar they were to the secret word.
After submitting a word, you will see its position. The secret word is number 1.
The algorithm analyzed thousands of texts. It uses the context in which words are used to calculate the similarity between them.
Begin with your first guess
Alright, let’s play Contexto!
🧠 My first guess is:
“apple”
What’s the rank?
1465
Thanks! 1465 is pretty far off, so let’s pivot.
My next guess is:
“fruit” 🍎
What’s the rank?
4423
Whoa — 4423 is even worse!
Let’s try:
“computer” 🖥️
What’s the rank?
2432
2432 — better than “fruit,” but still not close.
Let’s test:
“technology”
What’s the rank?
15264
Yikes — 15264 means we’re way off.
Let’s try a different angle:
“iphone”
What’s the rank?
The algorithm answered “I’m sorry, I don’t know this word”
Helpful! “iPhone” being unknown likely rules out brand names.
Let’s go generic:
“tree” 🌳
What’s the rank?
10620
Still off. Let’s test the education symbol of “apple”:
“teacher” 🍎📚
What’s the rank?
8984
Okay — not promising.
Let’s go more general and concrete:
“banana” 🍌
What’s the rank?
25726
Whoa. Let’s go symbolic:
“gift” 🎁
What’s the rank?
4309
Better! Let’s go deeper into symbolism:
“temptation” 😈🍎
What’s the rank?
764
🔥 Getting close!
Next guess:
“desire” 💭❤️
What’s the rank?
38
🎯 38?! We’re so close!
Next guess:
“lust” 😈❤️🔥
What’s the rank?
8
🔥🔥🔥 Only 7 away!
Try:
“passion” ❤️🔥
What’s the rank?
109
Still warm — but not hotter than “lust.”
Next guess:
“seduction” 😏
What’s the rank?
4183
Too cold — let’s try:
“sex”
What’s the rank?
3153
Worse — let’s go abstract again:
“craving” 😩
What’s the rank?
734
Warmer again! Let’s test a Deadly Sin:
“greed” 💰😈
What’s the rank?
14
🔥 Even closer than “desire”! Try another sin:
“envy” 👀💚
What’s the rank?
you got it!
🎉 LET’S GO!! ENVY for the win! 💚👀🔥
Nice job sticking with it — we cracked the pattern:
- “Apple” → temptation
- “Temptation” → “lust”
- “Lust” → “greed” → ENVY
Wanna play another round? 😄
Reflection
Well.. it took Chat 17 guesses to get to the right answer! Personally, I dont think this is very bad. If you have played the game before and done better, congrats!
I find it very interesting that this specific model uses SO MANY emojis… to the point that it kinda gets on my nerves.
I think the model does this to attempt to mimic younger audiences (specifically in the way that they text one another, but I’m not sure)
In addition, I found it pretty odd that it went from refined concepts to broader concepts. Usually when I play this game I start with very broad concepts and then narrow my scope from there (think emotion, object, food, etc). Chat went from apple to fruit and was surprised when it was further from the answer.