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75 of the Most Confusing Questions To Ask

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75 of the Most Confusing Questions To Ask

Question games and activities are everywhere.

You’ve likely asked or answered dozens of get-to-know-you types of questions. 

But if you’re looking for something new and unexpected to break the ice, why not try some nonsensical, confusing questions they won’t see coming?

They can enliven a conversation and help people think differently, whether at a party or just chatting with friends or family.

Questions that don’t make sense can prompt us to think outside the box, open us to new possibilities, and challenge our beliefs. 

They can be confounding, thought-provoking, and inspiring – but more than anything else, they will generate conversations that make us laugh and think.

So if you want to explore life’s unanswerable brain-stumpers and mind-benders, we have you covered with some confusing questions to ask to get the conversation rolling.

What Is a Nonsense Question?

A nonsense question can be hard to define because it must be meaningless but somewhat answerable.

Generally speaking, a nonsense question does not logically make sense at first but leads someone down a thought-twisting path to find a creative answer.

These questions can be tricky and fun, or they can even be confusingly deep!

Here are some responses you may expect when sharing a confusing or nonsensical question:

  • They make people think differently: Most people have automated responses to simple questions, but nonsense questions throw that out the window.
  • They elicit laughter: Most nonsense questions are funny and can bring a little lightheartedness to any conversation.
  • They make people curious: Nonsense questions lead to more confusing and interesting conversations, as they often require creative solutions or answers that don’t exist.
  • They don’t always have an obvious right or wrong answer: Nonsense questions often have multiple possible interpretations and many confusing answers.
  • They may elicit an emotional response: Since nonsense questions throw people off-guard, they can provoke an emotional response.

These responses make confusing questions much more interesting or revealing to ask, which can lead to a richer conversation.

If the question is confusing enough, it can even shut a conversation down!

75 of the Most Confusing Questions To Ask To Break The Ice

And now, here are 75 interesting yet confusing questions, divided into categories ranging from funny unanswerable questions to deeply profound ones.

They’re sure to get your creative juices flowing in conversation:

Funny Confusing Questions

1. Do fish ever get thirsty?

2. Why doesn’t the wool on a sheep shrink when it rains?

3. Would a fly without wings be called a walk?

4. Is a tree really wise if it can’t talk?

5. If the plural of mouse is mice, what’s the plural of spouse?

person in a seminar talking most confusing questions to ask

6. Why do we use the #2 pencil instead of the #1 pencil?

7. If your hand has a palm, is it a tree?

8. How come pencils need to be sharpened, but pens don’t?

9. Why do we press harder on a remote control when the batteries are running low?

10. If roses are red, then why are violets blue?

11. What happened in your last good conversation with your dog?

12. Do people eat or drink their soup?

13. Why don’t cats have nine lives like they used to?

14. Do mermaids lay eggs like fish or give birth like humans?

Questions That Make No Sense

15. Is nothing everything, or is everything nothing?

16. If you and I are different individuals, then how is it that we can’t trade places? Why isn’t “you” me, and why aren’t “I” you?

17. What name does an animal call itself? Is a dog known as a dog in dog language?

18. Why can’t I see everyone when I’m alone and know others exist in my mind?

19. If mirrors don’t reflect each other, why can I see myself in the mirror?

20. Is there a way to go up and down at the same time?

21. How can you think of something that doesn’t exist?

22. Can one person be two people at once?

23. What color is your invisible friend?

24. What are you doing in your dreams while you’re awake?

25. Does time ever run out?

26. Can fire be put in the water?

27. What dimension do you live in?

28. Who let the dogs out?

29. If money doesn’t grow on trees, then why do banks have so many branches?

30. What time is it on the sun?

Confusing Questions to Ask Your Friends

31. Do you want to meet me yesterday for lunch?

32. Did you think of my idea before or after I thought of it?

33. When do you stop being you?

34. Why can’t we see the future even if it’s already happened?

35. What did you do before now?

36. If I’m here and you’re there, then who is everywhere?

friends drinking laughing most confusing questions to ask

37. What do your dreams smell like?

38. Is friendship like a boat for you?

39. If you had to do it over again, would you?

40. If we wanted to, could we fly to the moon?

41. How many colors do you see in a rainbow?

42. Is it possible to turn back time?

43. What would you do with more than 24 hours in a day?

44. Are you your own best friend, and if so, why?

45. Am I your friend or a figment of your imagination?

46. Can we count to infinity together?

47. If you feel lost, why are you here?

48. Am I telling a lie or the truth when I say I’m telling you the truth?

49. Is my truth the same truth as your truth?


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Confusing Questions That Make You Think

50. What are you doing when you’re doing nothing?

51. Can life be complete without death, or does death give meaning to life?

52. Do thoughts travel faster than light?

53. How can something be “new and improved” if it’s never been used before?

54. Is there such a thing as outside, or is everything within your head?

55. How do you know when you really know something?

56. Is time a loop, a straight line, or a spiral?

57. Is a thought just a thought, or can it be anything you want it to be?

58. What’s the difference between imagination and reality?

60. What would happen if we were all honest with each other at the same time?

Trippy Questions

61. Does time have an end, or is it infinite?

62. Is the universe truly random, or are we just too small to see its order?

63. Is there anything in life that’s truly certain? If so, how are you certain?

64. Do souls get sick?

65. Are we living in an alternate universe?

66. What if your dreams are real?

67. Are memories collective or individual?

68. Does every action have an equal and opposite reaction, and if so, why don’t we see it in action?

69. What lies beyond the boundaries of space and time? Can our bodies or consciousness ever transcend this boundary?

70. Is life a random pattern or predetermined by a higher force?

71. Is technology expanding or limiting our consciousness?

72. What is the meaning of life if life contains all meanings?

group of friends laughing together most confusing questions to ask

73. If thoughts are energetic vibrations, then what is the power source that fuels them?

74. Is the earth a single organism, and we are simply under the illusion that we are individual beings?

75. How can we be a single entity when we are made up of millions, if not billions, of many different parts?

How to Use These Unanswerable Questions

Sometimes confusing questions can lead to interesting conversations and deeper insights. But if you use them at the wrong times, people may think that you’re just trying to be confusing.

When asked in the right context, unanswerable questions can be a great way to get people thinking about life’s bigger questions and mysteries.

Here are some ideas for when and how to use these confusing questions:

  • Use them as an icebreaker at parties or gatherings: Try using random but thought-provoking questions to get the conversation going when there’s a lull in a room. Unusual questions can really help to make people feel more comfortable by distracting them from their anxiety.
  • Start an intellectual debate: Arrange a group to ask pressing unanswerable questions and discuss their opinions. A friendly back-and-forth can lead to some interesting insights if everyone listens and responds respectfully.
  • Incorporate them into creative storytelling and writing: Use confusing questions as plot points in a story or narrative you’re creating by yourself or with a group of friends. This can deepen a story and make it more interesting. 
  • Play around with them during dinner: Ask your family confusing questions over dinner to get the conversation flowing. This is a great approach if you’re feeling bored or the dinner routine has gotten stale.
  • Share them online: Post interesting, confusing questions on social media to get people thinking and debating.
  • Use confusing questions to explore yourself: Reflect on life’s unanswered questions and journal your thoughts.
  • Turn these questions into a game: You could easily gamify them by writing them on paper, putting them in a jar, and having people randomly select one. To keep score, people can vote for the best answer after everyone’s response, and the most popular answer can earn a point.

No matter how you use confusing questions, remember that the goal is to have an open-minded conversation.

Some of these questions won’t have a definite answer, but they can still provide valuable insight into our thoughts and beliefs about life.

Final Thoughts

You’ll be surprised by many of the answers you’ll get and conversations you’ll have when you start using confusing questions in your everyday life. 

Whether they lead to profound insights or just a few laughs, unanswerable questions can be a great way to spark creativity and thought-provoking discussions!

Want to break the ice when you're with friends? Try asking these most confusing questions to ask we've collected in this post.

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