Whether you want to challenging yourself by figuring out a trick question or two, or can’t wait to send some hilariously confusing questions to your group chat, this list is full of funny, good questions to ask people.
But before you read any further, a word to the wise: These witty, trick questions are more challenging than they seem! Some of these confusing questions will get you laughing thanks to a play on words, while others are so complex they’ll make you see things in a whole new light.
So if you dare, test your wit by seeing how many of these 75 trick questions you can answer—before you start peeking at the answers. Then, send some of the most confusing questions to your friends and prepare yourself for all sorts of hilarious responses.
75 Trick Questions
1. What are two things you can never eat for breakfast?
Lunch and Dinner
2. What is always coming but never arrives?
3. What gets wetter the more it dries?
4. What can be broken but never held?
5. What word is spelled incorrectly in every single dictionary?
6. What is it that lives if it is fed, and dies if you give it a drink?
7. What never asks a question but gets answered all the time?
8. What word would you use to describe a man who does not have all his fingers on one hand?
Normal, because people usually have half their fingers on one hand.
9. What goes up but never ever comes down?
10. What can one catch that is not thrown?
11. A girl fell off a 50-foot ladder but didn’t get hurt. How come?
She fell off the bottom step
12. If you have one, you want to share it. But once you share it, you do not have it. What is it?
13. What starts with “e” and ends with “e” but only has one letter in it?
14. If a plane crashes on the border between the United States and Canada, where do they bury the survivors?
Survivors aren’t buried!
15. How can a girl go 25 days without sleep?
She sleeps at night
16. If it takes eight men ten hours to build a wall, how long would it take four men?
No time, because the wall is already built
17. You spot a boat full of people but there isn’t a single person on board. How is that possible?
Everyone on board is married
18. If you have a bowl with six apples and you take away four, how many do you have?
The four you took
19. How do you make the number one disappear?
Add a ‘G’ and it’s gone!
20. If you had only one match and entered a dark room containing an oil lamp, some kindling wood, and a newspaper, which would you light first?
21. What’s greater than God and more evil than the devil. Rich people want it, poor people have it. And if you eat it, you’ll die?
22. If you spell “sit in the tub” s-o-a-k, and you spell “a funny story” j-o-k-e, how do you spell “the white of an egg”?
23. A cowboy rode into town on Friday. He stayed in town for three days and rode out on Friday. How is that possible?
His horse is named Friday
24. Is it legal for a man to marry his widow’s sister?
No, but since he is dead it would be hard to do so.
25. What two keys can’t open any door?
A monkey and a donkey
26. If Mrs. John’s one-story house is decorated completely in pink, with the walls, carpet, and furniture all shades of pink, what color are the stairs?
There are no stairs
27. What will you actually find at the end of every rainbow?
The letter ‘W’
28. How did the boy kick his soccer ball ten feet, and then have it come back to him on its own?
He kicked it up
29. A young boy was rushed to the hospital emergency room, but the ER doctor saw the boy and refused to operate. “This boy is my son,” the doctor said. But the doctor wasn’t the boy’s father. How could this be?
The doctor was the boy’s mom
30. How could a man go outside in the pouring rain without protection, and not have a hair on his head get wet?
He is bald
31. What has a face and two hands, but no arms or legs?
32. If an electric train is moving north at 100mph and a wind is blowing to the west at 10mph, which way does the smoke blow?
An electric train has no smoke
33. I start out tall, but the longer I stand, the shorter I grow. What am I?
34. How was it possible that every single person in an airplane crash died, but two people survived?
The two survivors were married.
35. How many seconds are there in a year?
Twelve. January 2nd, February 2nd, March 2nd, etc.
36. What breaks and never falls, and what falls and never breaks?
Day breaks and night falls
37. What can run but not walk?
38. Some months have 31 days, others have 30 days, but how many have 28 days?
39. Thanks to me, you can see straight through the wall. What am I?
40. “The attorney is my brother,” testified the accountant. But the attorney testified he did not have a brother. Who is lying?
Neither one, because the accountant was his sister
41. Which weighs more, a pound of feathers or a pound of bricks?
Neither. They both weigh exactly one pound
42. Uncle Bill’s farm had a terrible storm and all but seven sheep were killed. How many sheep are still alive?
43. How can the pocket of your pants be empty, but still have something in it?
When the something is a hole.
44. What do you call a woman who knows where her husband is all the time?
45. What has a thumb and four fingers but isn’t actually alive?
46. What do you sit on, sleep on, and brush your teeth with?
A chair, a bed, and a toothbrush
47. Imagine you’re in a room that’s filling up with water quickly. There are no windows or doors. How do you get out?
48. What goes up and down, but always remains in the same place?
49. Everyone in the world needs it, but they usually give it without taking it. What is it?
50. What happened when the wheel was invented?
It caused a revolution
51. What can you hold without touching it at all?
52. What has a head, a tail, but does not have a body?
53. I am an odd number. Take away one letter and I become even. What number am I?
Seven (take away the ‘s’ and it becomes ‘even’)
54. Who is bigger, Mr. Bigger, Mrs. Bigger, or their baby?
The baby, since he is a little Bigger.
55. I’m light as a feather, but not even the strongest girl can hold me for more than 5 minutes. What am I?
56. If you sit a cup on the table facing south while you are on the north side of the table, on which side is the cup’s handle?
No matter which way the cup is turned, the handle is always on the outside
57. Two mothers and two daughters went out to eat, everyone ate one slice of pizza, yet only three slices were eaten. How’s that possible?
The group included a grandmother, her daughter and her daughter’s daughter.
58. A man lives on the 100th floor of an apartment building. On rainy days he rides the elevator all the way up. However, on sunny days, he goes half way and takes the stairs the rest of the way. Why?
The man is short and can only reach the button for the 50th floor on the elevator. On rainy days, he uses his umbrella handle.
59. What 5-letter word becomes shorter when you add two letters to it?
60. A man dressed in all black is walking down a country lane. Suddenly, a large black car with no lights on comes around the corner and screeches to a halt. How did the car’s driver know he was there?
It was day time
61. Can you name three consecutive days without using the words Wednesday, Friday, and Sunday?
Yesterday, today, and tomorrow
62. Robert, my neighbor, a forty-five-year-old blacksmith is seven feet tall, and eats all day long. What does he weigh?
63. What gets sharper the more you use it?
64. There are three important rooms in a house. The first one is filled with money. The second one is filled with important papers. The third one is filled with jewelry. One day all of these rooms burst into fire. Which room did the policemen put out the fire in first?
None of them, because policemen do not put out fires; firemen do
65. What can you make that no one—not even you—can see?
66. Why are 1968 pennies worth more than 1967 pennies?
Because there is one more penny in 1968 pennies than in 1967 pennies
67. What belongs to you but gets used by everyone else more than you?
68. There are eight men sitting on a couch. Three legs break and six men leave. How many legs are remaining?
Five; the legs of the two remaining men and the remaining couch leg.
69. You are driving a bus. When you begin your route, there is an old woman named Mrs. Smith and a young boy named Raymond are on the bus. At the first stop, the old woman leaves, and a salesman, named Ed, enters. At the next stop, Jack and his sister Jill get on, as well as three women with shopping bags. The bus travels fifteen minutes, then stops and Raymond gets off and a man and his wife get on. Next, a woman with a bird in a cage gets on the bus. What is the name of the bus driver?
70. What occurs once in a minute, twice in a moment, and never in one thousand years?
The letter M
71. What is the maximum number of times a single page of a newspaper can be folded in half by hand?
72. I’m so fragile that if you say my name, you’ll break me. What am I?
73. On a Sunday morning, the oldest girl in a family was murdered. The father was reading the paper, the mother was in the kitchen cooking breakfast, and the girl’s brother was playing video games. Uncle George was visiting and was out getting the mail. Who murdered the girl?
Uncle George. Mail isn’t delivered on Sundays
74. What’s full of holes but can still hold liquid?
75. What two words, when combined, hold the most letters?