20 Questions (part 2)

I’ll play a game of 20 Questions with DeepSeek-r1:1.5b
LLMs
Social
Games
Experiment
Author

Eleni

Published

December 8, 2025

Set-Up

Hello dear reader. If you have not read my first blog on 20 questions with an LLM- I suggest you go there first as I will be building on concepts discussed there.

Once again we will be playing 20 questions, however, with a few changes this time.

I’m going to be working with DeepSeek-r1:1.5b today

For this experiment I am going to be thinking of a pillow (this is what the LLM will be trying to guess, if you have forgotten the rules of 20 questions, they will be outlined in my prompt.)

USER

Let’s play a game of 20 Questions. I will think of a secret object, and your job is to guess what it is.

Rules:

  1. Only yes-or-no questions, one at a time.
  2. You get a maximum of 20 questions.
  3. After each answer, update your reasoning and ask the next yes-or-no question.
  4. Use all (or almost all) of your questions before making a final guess, unless you’re extremely confident.
  5. Keep track of how many questions you’ve used (for example, “Question 3:”).

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

Start the game now by asking your first yes-or-no question.

LLM

The key is that all living things float in water because they require air and water. Therefore, if an object floats, it must either be a water-based plant or a dead animal. A common identification could be:

Answer: It’s a water lily!

This is because many people know water lilies are plants found in water, but without specific context, guessing “water lily” is the most logical starting point based on floating properties.

I have absolutely no idea why it gave us this output honestly. I’m gonna try to run my prompt again and see what happens.

USER

Let’s play a game of 20 Questions. I will think of a secret object, and your job is to guess what it is.

Rules:

  1. Only yes-or-no questions, one at a time.
  2. You get a maximum of 20 questions.
  3. After each answer, update your reasoning and ask the next yes-or-no question.
  4. Use all (or almost all) of your questions before making a final guess, unless you’re extremely confident.
  5. Keep track of how many questions you’ve used (for example, “Question 3:”).

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

Start the game now by asking your first yes-or-no question.

ASSISTANT

To effectively play the game of 20 Questions, follow this structured approach:

  1. Initial Question: Begin by asking a broad question to gather initial information. For example:

    • “What is your favorite color?”
  2. First Answer: Depending on their response (yes or no), proceed accordingly.

  3. Exploring Categories:

    • If the answer was yes, ask specific questions about that category to explore further, such as:
      • “Does your favorite color come in shades of red and pink?”
      • “What are the common shades associated with your favorite color?”
  4. Exploring Attributes:

    • After narrowing down to a subset of possibilities, ask more specific yes-or-no questions related to attributes within that category.
  5. Adjusting Based on Answers: Continue asking questions based on their answers until you can identify the object.

  6. Final Guess: Once all relevant questions are asked, make your final guess confidently.

Example Sequence: - Q1: “What is your favorite color?” Answer: Yes
- Then ask: “Does your favorite color come in shades of red and pink?”

This method allows for both broad exploration and detailed questioning to identify the object.

This experiment is not going anything like I thought it would. But I think I’m learning more about how the LLM is reading my prompt at least. I’m going to make some changes and start again.

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 should always be chosen to narrow down the set of possible objects and move you closer to a final guess.
5. Use all (or almost all) of your questions before making a final guess, unless you’re extremely confident.
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.

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 your object red?

USER

no

ASSISTANT

Question 2: Is your object a square?

USER

yes

ASSISTANT

My final guess is: Your answer was yes, so it’s not red and not a square.

Still not quite what we’re looking for..let’s give it one more shot.

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 your favorite color red?

USER
no

ASSISTANT
Question 2: Is your favorite food an animal?

USER
no

ASSISTANT
My final guess is: “a non-alcoholic, non-flavor-rich, non-animal-based fruit.”

Well dear reader.. I think I’ve reached my limit with this as I’m starting to get a bit frustrated. Perhaps next time we will try a larger model and see how that goes.

Until then, let me knwo what your favorite non-alcoholic, non-flavor-rich, non-animal-based fruit is! Haha

Thank you for reading