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?
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?
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?
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?
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?
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!
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. Learn more about Tom on our About page.