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75 Confusing and Funny Trick Questions To Ask Anyone

A photo of Tom who is the Co-Founder of Questions About Everything

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These trick questions to ask anyone are perfect if you’re looking to confuse a few friends and get them thinking.

We have a great list of confusing questions that will make even the sharpest minds pause for thought. Some are funny, some are hard, but all are guaranteed to lead to interesting conversations.

Tricky questions are ideal to use with people you’re familiar with as a fun way to get them talking. They’re also perfect to ask kids as they will spark their imaginations into action.

So why not try out these tricky questions to ask friends and family today and see what happens!

Trick Questions

1. What’s something that can be broken but never held?

Answer: Promises

2. What’s the only word in the dictionary that’s spelt incorrectly?

trick question to ask anyone on what the only word in the dictionary is that's spelt incorrectly

Answer: Incorrectly

3. What are the only two things you can’t eat for breakfast?

Answer: Lunch and dinner

4. What always increases but will never come down?

Answer: Your age

5. What can you catch but never throw?

Answer: A cold

6. What’s something that starts and ends with ‘e’ but only has one letter in it?

Answer: An envelope

7. What two keys are unable to open a door?

Answer: Donkey and Monkey

8. You may not find a pot of gold at the end of a rainbow, but what’s one thing you will do?

Answer: A ‘w’

9. What has a face and two hands but doesn’t have any arms or legs?

Answer: A clock

10. What’s something that starts out tall but gradually becomes shorter the longer it stands?

Answer: A candle

11. There are months that have 30 days and months that have 31 days, but how many months have 28 days?

Answer: Twelve

12. Does a pound of feathers or a pound of bricks weigh more?

Answer: They both weigh a pound

13. I go up and down but I always remain in the same place, what am I?

Answer: Stairs

14. What’s something you can hold but never touch?

Answer: A conversation

15. What has no body but a head and a tail?

Answer: A coin

16. Which five-letter word becomes shorter if you add two letters to it?

Answer: Short

17. What’s something all of us can make but none of us can see?

confusing question to ask someone: what's something all of us can make but none of us can see

Answer: Noise

18. What’s something that belongs to you that’s used more by others than yourself?

Answer: Your name

19. What is so fragile that if you say its name you’ll break it?

Answer: Silence

20. What can hold liquid despite being full of holes?

Answer: A sponge

21. What has teeth but is unable to eat?

Answer: A comb

22. What bird is able to lift the most weight?

Answer: A crane

23. As soon as the rain comes down what goes up?

Answer: An umbrella

24. What cannot walk but has three feet?

Answer: A yardstick

25. What’s something that’s able to travel the world despite being stuck in one spot?

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Answer: A stamp

26. What’s a room that has no walls?

Answer: A mushroom

27. What’s something that has no neck despite having a head?

Answer: A bottle

28. What country is the coldest in the world?

Answer: Chile

29. Does heat or cold move faster?

Answer: Heat, because it’s always possible to catch a cold

30. What’s something that will get bigger the more you remove from it

Answer: A hole

31. What has four legs, a head and one foot?

Answer: A bed

32. What was the tallest mountain on the planet before the discovery of Mount Everest?

Answer: Mount Everest

33. What’s something that never talks but babbles?

Answer: A brook

34. What word in the dictionary has a weird spelling?

Answer: Weird

35. What can hold without ever touching it?

Answer: Your breath

36. What’s something that has no bones but has a spine?

Answer: A book

37. What’s something that you leave behind you the more you move forward?

tricky question on what's something you leave behind you the more you move forward

Answer: Footprints

38. I have one eye but I can’t see anything, what am I?

Answer: A needle

39. If a rooster lays an egg on top of the barn, which way will it roll?

Answer: It won’t roll because roosters don’t lay eggs

40. What word in the language has the same pronunciation if you take away the last four letters out of five?

Answer: Queue

41. What’s something that can fill an entire room despite taking up no space?

Answer: Light

42. What’s something that can taste but never smell?

Answer: A tongue

43. What kind of tree are you able to hold in your hand?

Answer: Palm tree

44. Someone has married many men but has never been married, how is this possible?

Answer: They are a minister

45. What coat is best to put on when it’s wet?

Answer: A coat of paint

46. When do you know a clock is hungry?

Answer: When it goes back four seconds

47. What’s something that has four legs and one head, but many hungry mouths?

Answer: A dining table

48. What happens every time the ocean meets the beach?

Answer: It waves

49. What never asks a question but is always answered?

Answer: A cellphone

50. What’s at the beginning of everything?

Answer: The letter ‘e’

51. What type of cheese is made backward?

Answer: Edam

52. When does 1+1 not equal 2?

Answer: When you make a mistake

53. What three letters will turn a girl into a woman?

Answer: Age

54. What building has the most stories out of any in the world?

trick question for adults on the building that has the most stories out of any in the world

Answer: A library

55. Why can’t someone living in the UK be buried in America?

Answer: People who are alive can’t be buried anywhere

56. Where would you find an ocean with no water?

Answer: On a map

57. What nail does a builder always want to miss?

Answer: Their fingernail

58. What’s something you buy for dinner but wouldn’t eat?

Answer: A knife and fork

59. Why do Eskimos never hunt penguins?

Answer: Eskimos live at the North Pole while penguins live at the South Pole

60. How many letters are in the alphabet?

Answer: Eleven letters are in ‘the alphabet’

61. What’s something that starts with the letter ‘T’, is full of ‘T’, and ends in ‘T’?

Answer: A teapot

62. Is it legal for a man to marry the sister of his widow?

Answer: No, because he’s dead

63. What’s one type of dress that can never be worn?

Answer: An address

64. How is it possible to make a room that’s full of people vanish?

Answer: Turn off the lights

65. What’s something that grows larger the more you live?

Answer: Your memory

66. What’s the commonly used letter in Sweden?

Answer: E, it’s used twice

67. How many stars are still in the sky when it’s daylight?

Answer: All of them

68. What’s something that has three wheels and flies?

Answer: An aeroplane

69. Which word becomes harder to spell if you drag it out?

Answer: Hard

70. What’s something that you can wear all day without ever needing to put it on?

Answer: A beard

71. What’s something that always tells the truth despite not having a mouth?

trick question on something that always tells the truth despite not having a mouth

Answer: A mirror

72. What belt is more valuable than the finest suits?

Answer: A seatbelt

73. What has every person who’s ever been in a boat sailed toward but never reached?

Answer: The horizon?

74. What can sleep silently for centuries but cause chaos for those nearby when it wakes?

Answer: A volcano

75. What type of TV watches you?

Answer: CCTV

Looking For More Questions?

21 Questions Game – A fun game you can play with your friends that will lead to a lot of fun conversations.

Yes or No Questions – A different set of questions that will give you an insight into what people think about certain situations.

Critical Thinking Questions – Do some more hard thinking with these questions that will require a lot of brainpower!

Hard Would You Rather Questions – A fiendishly difficult version of the fun party game!

A photo of Tom who is the Co-Founder of Questions About Everything

Tom Stevenson

Co-Founder of Questions About Everything

Tom is a travel writer and Co-Founder of Questions About Everything. He grew up in the UK and enjoys spending his time traveling to new places, supporting Liverpool FC, and blogging about his adventures. He spent two years teaching English in Barcelona and frequently utilized question games and conversation starters as part of his lesson plans. As an EFL teacher, he took full responsibility for planning and delivering lessons, frequently employing creative and diverse questions to engage the children in conversation. Learn more about Tom on our About page.