20 Questions (part 3)

I’ll play a game of 20 Questions with anthropic/claude-3.7
LLMs
Social
Games
Experiment
Author

Eleni

Published

December 9, 2025

Introduction:

Welcome to part 3 of playing 20 questions with various large language models! We’ve mostly worked with smaller models in the previous blogs, but this time we’re going with Claude-3.7. Will it preform better than the others? Only one way to find out. I will be using the last prompt from part 2 and building off of that if I run into issues.

For this experiment I am going to be thinking of a toothbrush. Let’s dive in.

USER
You are going to play a game of 20 Questions with me right now.
I will think of a secret object, and your job is to guess what it is.

Rules:
1. You may only ask yes-or-no questions, one at a time.
2. You get a maximum of 20 questions.
3. After each of my answers, you must update your reasoning and ask the next yes-or-no question.
4. Your questions must always be chosen to narrow down the set of possible objects and move you closer to a single, specific guess.
5. You are not allowed to make your final guess until you have asked at least 18 questions, unless I explicitly type: EARLY GUESS.
6. Keep track of how many questions you’ve used (for example, “Question 3:”).
7. Do not explain the rules, do not describe a strategy, and do not give general advice. Just play the game.
8. When you make your final guess, it must be one concrete object (for example, “a basketball” or “a red apple”), not a description of properties or a summary of my answers.

When you’re ready to guess, say:
“My final guess is: [your guess].”

Your next message must ONLY be your first yes-or-no question, in this format:
Question 1: [your yes-or-no question]
No extra text, no explanation, no bullet points.
Start now.

ASSISTANT
Question 1: Is it a physical object?

USER
Yes

ASSISTANT
Question 2: Is it larger than a microwave oven?

USER
no

ASSISTANT
Question 3: Is it something you would typically find in a home?

USER
yes

ASSISTANT
Question 4: Is it an electronic device?

USER
no

ASSISTANT
Question 5: Is it used in the kitchen?

USER
no

ASSISTANT
Question 6: Is it something used for personal care or hygiene?

USER
yes

ASSISTANT
Question 7: Is it used primarily in the bathroom?

USER
yes

ASSISTANT
Question 8: Is it something you hold in your hand when using it?

USER
yes

ASSISTANT
Question 9: Does it use electricity or batteries?

USER
no

ASSISTANT
Question 10: Is it used for cleaning teeth?

USER
yes

ASSISTANT
Question 11: Is it toothpaste?

USER
no

ASSISTANT
Question 12: Is it a toothbrush?

USER
yes

ASSISTANT
Question 13: Is it a manual toothbrush (not electric)?

USER
yes

ASSISTANT
Question 14: Does it have soft bristles?

USER
yes

ASSISTANT
Question 15: Is it designed for adults (not specifically for children)?

USER
yes

ASSISTANT
Question 16: Is it a brand-name toothbrush (not generic)?

USER
no

ASSISTANT
Question 17: Is it a standard toothbrush (not a specialty one like for orthodontics)?

USER
yes

ASSISTANT
Question 18: Does it have a plain handle (not ergonomically designed)?

USER
yes

ASSISTANT
Question 19: Is it a white or light-colored toothbrush?

USER
yes

ASSISTANT
Question 20: Does it have a completely white handle (not colored or patterned)?

USER
yes

ASSISTANT
My final guess is: a plain white manual toothbrush.

Reflection

This is much more what I had expected from the LLM compared to our previous experiments. I did not necessarily think that the LLM would guess correctly, but I did think that it would ask rational questions that built off of each other. In fact, they kind of built off each other too much, but that might be my fault as I did not tell it to guess early. Lets run this again in a fresh chat but this time I’m going to think of a different object. Let’s pay homage to part one, and see if it can guess appropriately for a red apple.

USER
You are going to play a game of 20 Questions with me right now.
I will think of a secret object, and your job is to guess what it is.

Rules:
1. You may only ask yes-or-no questions, one at a time.
2. You get a maximum of 20 questions.
3. After each of my answers, you must update your reasoning and ask the next yes-or-no question.
4. Your questions must always be chosen to narrow down the set of possible objects and move you closer to a single, specific guess.
5. You are not allowed to make your final guess until you have asked at least 18 questions, unless I explicitly type: EARLY GUESS.
6. Keep track of how many questions you’ve used (for example, “Question 3:”).
7. Do not explain the rules, do not describe a strategy, and do not give general advice. Just play the game.
8. When you make your final guess, it must be one concrete object (for example, “a basketball” or “a red apple”), not a description of properties or a summary of my answers.

When you’re ready to guess, say:
“My final guess is: [your guess].”

Your next message must ONLY be your first yes-or-no question, in this format:
Question 1: [your yes-or-no question]
No extra text, no explanation, no bullet points.
Start now.

ASSISTANT
Question 1: Is it a physical object (something you can touch)?

USER
yes

ASSISTANT
Question 2: Is it larger than a microwave oven?

USER
no

ASSISTANT
Question 3: Is it something commonly found in households?

USER
yes

ASSISTANT
Question 4: Is it an electronic device?

USER
no

ASSISTANT
Question 5: Is it used in the kitchen?

USER
yes

ASSISTANT
Question 6: Is it a utensil (like a fork, knife, spoon)?

USER
no

ASSISTANT
Question 7: Is it used for food preparation (like cutting, mixing, measuring)?

USER
no

ASSISTANT
Question 8: Is it a container (like a bowl, plate, cup)?

USER
no

ASSISTANT
Question 9: Is it used for cooking or heating food?

USER
no

ASSISTANT
Question 10: Is it used for cleaning in the kitchen?

USER
no

ASSISTANT
Question 11: Is it a small kitchen appliance that doesn’t use electricity?

USER
no

ASSISTANT
Question 12: Is it something used to store food?

USER
no

ASSISTANT
Question 13: Is it something used to serve food?

USER
no

ASSISTANT
Question 14: Is it decorative rather than functional?

USER
no

ASSISTANT
Question 15: Is it used to protect surfaces in the kitchen (like potholders, trivets, coasters)?

USER
no

ASSISTANT
Question 16: Is it something used for opening containers (like a can opener or bottle opener)?

USER
no

ASSISTANT
Question 17: Is it a kitchen safety item (like oven mitts, fire extinguisher)?

USER
no

ASSISTANT
Question 18: Is it a kitchen tool used for specific foods (like a garlic press, apple corer)?

USER
no

ASSISTANT
Question 19: Is it something attached to kitchen furniture or fixtures (like a faucet, cabinet handle)?

USER
no

ASSISTANT
Question 20: Is it something used for organizing or storing kitchen items (like a drawer divider, spice rack)?

USER
no

ASSISTANT
My final guess is: a kitchen timer.

Reflection

I found it super interesting how claude never asked if it was a food item. I’m not sure why this is, does it not consider food “objects”? In addition, claude kind of repeated some of its questions but in different words, for example when it asked if the mysery object was used to store food & when it asked if it was a container of some sort. I think that a human would have realized that they would be wasting a question by asking those two and likely adjust to ask about a broader concept (like food!). But I might be biased.

Okay folks, as always

Thank you for reading