Whether you want to challenge 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 125 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.

125 Trick Questions

  1. What are two things you can never eat for breakfast? Lunch and Dinner
  2. What is always coming but never arrives?  Tomorrow
  3. What gets wetter the more it dries?  A towel
  4. What can be broken but never held?  A promise
  5. What word is spelled incorrectly in every single dictionary? Incorrectly
  6. What is it that lives if it is fed, and dies if you give it a drink? Fire
  7. What never asks a question but gets answered all the time? Your cellphone
  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? Your age
  10. What can one catch that is not thrown? A cold
  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? A secret
  13. What starts with “e” and ends with “e” but only has one letter in it? An envelope
  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? The match
  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? Nothing
  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”? E-G-G  W-H-I-T-E
  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? A clock
  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? A candle
  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? Rain drops
  38. Some months have 31 days, others have 30 days, but how many have 28 days? All 12
  39.  Thanks to me, you can see straight through the wall. What am I? A window
  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? Seven
  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? A widow
  45. What has a thumb and four fingers but isn’t actually alive? A glove
  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? Stop imagining
  48. What goes up and down, but always remains in the same place? Stairs
  49. Everyone in the world needs it, but they usually give it without taking it. What is it? Advice
  50. What happened when the wheel was invented? It caused a revolution
  51. What can you hold without touching it at all? A conversation
  52. What has a head, a tail, but does not have a body? A coin
  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? Breath
  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? Short
  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? Iron
  63. What gets sharper the more you use it? Your brain
  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? Noise
  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? Your name
  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? It’s you!
  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? Once
  72. I’m so fragile that if you say my name, you’ll break me. What am I? Silence
  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? A sponge
  75. What two words, when combined, hold the most letters? Post Office
  76. If a monkey, a squirrel, and a bird are racing to the top of a coconut tree, who will get the banana first? None, coconut trees don’t grow bananas.
  77. I have teeth but can’t eat. What am I? A comb
  78. First you throw away my outside and cook the inside. Then you eat my outside and throw away my inside. What am I? Corn on the cob. Because you throw away the husk, cook the corn. Then you eat the kernels, and throw away the cob.
  79. If ten birds are sitting in a tree and a hunter shoots one, how many birds are left in the tree? None, because after one bird got shot, the rest flew away
  80. What runs, but never walks. Murmurs, but never talks. Has a bed, but never sleeps. And has a mouth, but never eats? A river
  81. What has 4 wheels and flies? A garbage truck
  82. What bird can lift the most weight? A crane
  83. Why did the woman run around her bed at night? To catch up on her sleep
  84. What goes up as soon as the rain comes down? An umbrella
  85. How much dirt is there in a hole that is 3 feet deep, 6 feet long, and 4 feet wide? None, because a hole does not have any dirt inside
  86. The more you take, the more you leave behind. What am I?  Footprints
  87. How many legs does an elephant have if you count his trunk as a leg? Four, because calling the elephant’s trunk a leg does not make it one.
  88. I have all the knowledge you have. But I’m so small, you can hold me in your fist. What am I? Your brain
  89. How many animals did Moses take into the ark? None because it was Noah who built and loaded the ark
  90. What has three feet but can’t walk? A yardstick
  91. If a rooster lays an egg on top of the barn roof, which way will it roll? It will not roll, because roosters do not lay eggs
  92. If two’s company and three’s a crowd, what do four and five make? Nine
  93. How can you lift an elephant with one hand? You cannot, because you will never find an elephant with one hand
  94. What travels the world while stuck in one spot? A stamp
  95. How can you drop a raw egg onto a concrete floor and not crack it? No problem, because concrete floors are very hard to crack
  96. Name four days of the week that start with the letter “t”? Tuesday, Thursday, today, and tomorrow.
  97. Which room has no walls? A mushroom
  98. What has four eyes but can’t see? Mississippi
  99. Where is an ocean with no water? A map
  100. What’s as big as an elephant but weighs absolutely nothing? Its shadow
  101. How can a door be not a door? When it’s a jar
  102. What word starts with IS, ends with AND, and has LA in the middle? Island
  103. What has a neck but no head? A bottle
  104. What is the coldest country in the world? Chili
  105. What moves faster: heat or cold? Heat because you can always catch a cold.
  106. Forwards I’m heavy but backwards I’m not. What am I? A ton
  107. A girl leaves home and turns left three times, only to return home facing two guys wearing masks. Who are the two guys? The catcher and the umpire
  108. Beth’s mother has three daughters. One is called Lara, the other one is Sara. What is the name of the third daughter? Beth
  109. What gets bigger and bigger the more you take away from it? A hole
  110. I have one head, one foot, and four legs. What am I? Your bed
  111. What has one eye but can’t see anything at all? A needle
  112. If you were running a race and passed the person in second place, what place would you be in now? Second place
  113. If you threw a red rock into a green sea, what would it come back as?  Wet
  114. What kind of tree can you carry in your hand? A palm
  115. The teacher asked the two girls who looked exactly like the following questions: a.) Are you from the same family? b.) Do you have the same parents? c.) Were you born on the same day? They answered truthfully “yes” to those questions, and yet told the truth when they indicated they were not twins. How can this be? They were triplets
  116. A woman pushes her car to a hotel and then proceeds to tell the owner that she is bankrupt. Why? She is playing Monopoly
  117. If Mr Smith’s peacock lays an egg in Mr Jones’ yard, who owns the egg?  Peacocks don’t lay eggs
  118. A 10 foot rope ladder hangs over the side of a boat with the bottom rung on the surface of the water. The rungs are one foot apart, and the tide goes up at the rate of 6 inches per hour. How long will it be until three rungs are covered? Never. The boat rises as the tide goes up.
  119. A truck driver is going down a one way street the wrong way, and passes at least ten cops. Why is he not caught?  Because he was not driving! He’s walking on the sidewalk
  120. If a doctor gives you 3 pills and tells you to take one pill every half hour, how long would it take before all the pills had been taken?  1 hour! Take the 1st pill right away, half an hour later take the 2nd and half an hour after that the 3rd.
  121. Name the most recent year in which New Year’s came before Christmas. This year. New Year’s always comes before Christmas of the same year.
  122. How many times can you subtract 10 from 100?  Once. Next time you would be subtracting 10 from 90.
  123. Who’s buried in Grant’s tomb?  No one. Ulysses Grant is interred in Grant’s tomb but not buried.
  124. Before Mount Everest was discovered, what was the tallest mountain on Earth?  Mount Everest
  125. If the vice president were to die, who is supposed to be president? The President Keep the fun going by checking out this giant list of 250 “Would You Rather?” questions.
125 Trick Questions with Answers That Are Confusing - 77