154 Very Best Trick Questions

154 Very Best Trick Questions

Roll up, roll up, and test your wits with this catalog of conundrums! These trick questions are just the thing for anyone who wants to give their brain something to chew on.

Ranging from clever, to confusing, to just plain silly, we’ve got something for everyone. Whether you’re just looking for a quick diversion, or a long wander through the labyrinth, see how many of these you can guess without checking the answers first.

Either way, if you can make it to the other side, you’ll be armed with more than a few mind-melting riddles to torment others with, should you wish.

154 Trick Questions

1. What species of primate is capable of solving complex mathematical equations?

Human beings

2. Who can knock you unconscious, take your money and leave you with missing teeth, without breaking any laws?

A dentist

3. What is the simplest way to make a room full of people vanish?

Turn out the lights

4. What does logic tell us must, inevitably, be found at the end of time?

The letter ‘E’

5. What kind of building is filled with thousands of voices all day, but remains totally silent?

A library

6. What kind of nail can replace itself each time it is removed?


7. Where would you be certain to find the most refreshing drink you will ever taste?

In the middle of a desert

8. A sportsman in Wimbledon lines up his shot, strikes the ball, and watches it fly squarely into the net. Why is he pleased?

He’s playing football, not tennis

9. Colonel Sandford is found slumped across his writing desk in a study locked from the inside, dead of natural causes. One hand clutches a fragment of paper with a single word scrawled on it: “Many…”.  His wife, the last person to see Sandford alive, has been having an affair for several years with his older brother Thomas – a local priest. Sandford’s son from a previous marriage, Richard, stands to inherit most of his father’s estate. He attends the Reverend Sandford’s church mass every Sunday. Considering that today is a Tuesday, who murdered the Colonel?

Nobody – he died of natural causes

10. What part of you grows larger and larger, the longer you live?

Your memory

11. What must be broken into pieces, in order to function properly?

An eggshell

12. What is always holding you up, no matter where you go?

The soles of your shoes

13. What kind of device only ever answers one question, but always tells you exactly what you need to know?

A clock

14. An airline pilot staggers onto his plane three minutes before take-off, without his uniform and clearly a little drunk. Why is no-one on board concerned?

He is off duty, and only a passenger on this flight

15. What is an item people see as essential, but buy hoping they will never use it once?

A fire extinguisher

16. You write a message in a bottle, and throw it into the ocean off a remote Pacific island. The bottle is carried out to sea by the current and gradually makes its way around Cape Horn, before being drawn up the coast of South America. Eventually it is caught in the Gulf Stream and, over the course of many months, slowly bobs across the Atlantic. Finally the bottle washes up on the shores of Portugal, where it is found and opened. The message contains only a few sketches of the island, descriptions of its wildlife, and some clues about the time of year when it was written. How could you locate the person who originally wrote it?

Look in a mirror; it was you

17. What has four legs, one head, and many hungry mouths?

A dining table

18. In England, what is the most commonly used letter?

‘N’ – it appears twice

19. Assuming they were both unarmed, who would win a fight between a special forces commando, and an 18th-century samurai warrior?

The commando would win by default, his opponent having been dead for around 200 years

20. How many stars still remain in the sky, during daylight hours?

All of them

21. You pour three pints of water out of a gallon jug. Assuming the jug was full when you started, how many pints do you have?


22. A man runs out directly in front of an 18-wheel truck on an icy stretch of road, and is completely unharmed. How?

The truck was not moving

23. What kind of soup can you get from an egg?

Chicken soup

24. What is the cheapest way to buy thirteen diamonds?

Buy a deck of cards

25. You can find me once in Holland, twice as often in London, never in Rome but once in Naples. What am I?

The letter ‘N’

26. What animal is 1/3rd cow, 1/3rd ape, and 1/5th trout?


27. Those who do not have me are better off than those who do. A good restaurant would never serve me. If you eat me you die. What am I?


28. What has a long, graceful neck and can sing with a sweet voice, but has no mouth?

A violin

29. Which letter of the alphabet is most like me?

The letter ‘I’

30. What smells better than it tastes?

A nose

31. I am often given to those who don’t want me by those who do. After killing thousands, I can be remembered fondly by those I leave alive. What am I?


32. What has hands, but can never touch its own face?

A clock

33. What is ‘gravel’ made up of?

The letters G-R-A-V-E-L

34. When can the number five evenly divide seven in two?

When it’s the Roman numeral ‘V’

35. What is something you never asked for, seldom use yourself, but will carry with you every day for the rest of your life?

Your name

36. What is something you could catch after spending a long time in the cold and damp, that might actually make you healthier?

A fish

37. What can you step on with your right foot, but never your left?

Your left foot

38. I am always up when the weather’s terrible, and down again whenever the sun comes out. What am I?

An umbrella

39. During which month do people in Brazil eat the least?

February, as it is shorter than all the other months

40. When I was 6 years old, my mother was 33. If she is now twice my age, how old must I be today?

27 years old (the difference between our ages)

41. Before its dissolution in 1993, what was the capital of Czechoslovakia?

The letter ‘C’

42. Facing towards the sun, you begin walking down a flight of stairs. By the time you reach the last step, the sun is setting behind you. What happened?

It was a spiral staircase

43. What has three wheels and flies?

An aeroplane

44. Who can spend hours on end counting sheep, without ever falling asleep?

A shepherd

45. When can a man who stands at exactly four feet, be one meter tall?

When it’s a parking meter

46. How can a baby have been born before the doctors who delivered it?

In the sense that it was born in front of them

47. Whose services are needed most urgently by a man who does not know he needs them?

An undertaker

48. If a ship had a well trained crew, 300 gallons of fuel and three weeks’ worth of food, how far could it sail into the Atlantic Ocean?

Halfway – beyond that point, it would be sailing back out

49. How could a woman marry her own son, without anyone raising an objection?

If she were the priest officiating his wedding

Trick Questions: Part 2

50. What is that, with one flick of the wrist, will let you move something the strongest man on earth could not?

A key

51. I cover myself most thickly in Summer, wearing less and less the colder Winter gets. What am I?

A tree

52. I pick myself up and dust myself off but, before too long, I make one little slip and find myself shattered into a hundred pieces. What has happened?

I have dropped a mirror

53. How can you throw a hammer through a glass window without breaking it?

A hammer is tough, and unlikely to break

54. A man has a nightmare about being chased by a herd of stampeding cattle, which ends with him being trampled under their feet. When he wakes in the morning, real bruises have appeared on his body during the night. How is this possible?

He fell out of bed

55. What is always approaching faster than you think, but never actually arrives?

The future

56. Which day of the year has 23 full hours?

All of them

57. Which word do many people deliberately spell backwards?


58. Which is shorter, a year or twelve months?

A Y-E-A-R, with only five letters

59. Simon’s nephew has four uncles. Three of them are named Leonardo, Donatello and Raphael. What is the fourth uncle called?


60. What is not much use by itself, but always has a point?

A needle

61. What is located at the precise centre of America?

The letter ‘R’

62. How many times could you cut a whole grapefruit into halves?


63. If the second, third, fourth and sixth candidates in line for a country’s throne all died, who would end up wearing the crown?

Whoever wore it beforehand

64. Every member of a school, located near the coast, gets swept out to sea one day while swimming together. Nobody on land ever sees them again, but this is not a problem. Why?

It was a school of fish

65. What kind of man can be six feet tall at midday, shrink to three feet by the evening, and vanish entirely by the next morning?

A snowman

66. A man walks his dog, stops for breakfast at a cafe, then catches a bus into the middle of town. He works all day at a local call centre, then in the evening attends a concert before returning home. In all this time, he does not see another living person. How is that possible?

The man is blind

67. What kind of legal document is exactly the same, whether it’s read backwards or forwards?

The answer is a D-E-E-D

68. What feature of a room could an artist try drawing, to immediately change the way he sees it?

The curtains

69. In what sort of popular internet joke am I always mentioned twice?

A meme

70. Houdini’s assistant locks on the handcuffs, then climbs atop the water tank and holds its steel trapdoor open. Once the trapdoor has slammed shut, he secures it with a heavy padlock. A timer starts counting down from three minutes, as the captivated audience watches a fearsome struggle take place behind the glass. With one minute to go, the opened handcuffs drift down with a muffled clank – but after this, there are only desperate bangs against the trapdoor. The padlock rattles, but holds firm. A curtain is drawn across the tank as the final seconds count down, the crowd growing anxious. How will he be able to escape?

The assistant does not need to, he was never in the tank to start with

71. The spelling for this word becomes harder if you drag it out. What is it?


72. What appears in the middle of January, twice in August, and once in June?

The letter ‘U’

73. For fun, some girls try writing their names forward, backward, then upside down, just to see how they look. One of the group doesn’t bother, as she knows it would be pointless. What is her name?


74. What four-letter word can be cut down to a single letter, by removing only one?


75. What word sounds exactly the same, if you remove two-thirds of its letters?


76. I can cover an entire country, without anyone seeing me. What am I?


77. What can flatten entire cities, and make mighty nations bend this way or that?

A map

78. What will cause even the tallest, strongest wall to vanish into thin air?

A corner

79. When can you cut twelve faces, without spilling a drop of blood?

When cutting a deck of cards

80. What can you give to someone without wanting to, and still keep for yourself – while wishing that you could lose it?

A cold

81. You are in a horse race, and manage to gallop past the riders in fourth, third, and second place before you cross the finish line. Where did you come?

Second place

82. You have been struck by a small earthquake, which has now stopped completely – but one part of your house is still going up and down. Which part is it?

The staircase

83. If you hold onto me for too long, you might just lose me forever. What am I?

Your breath

84. What is something you can throw without meaning to, but could never catch however hard you tried?

Your shadow

85. David and Anne throw a party. It is a great success, filled with music, dancing, good food and laughter, despite the fact that not one single person showed up. What happened?

All their friends are married

86. What can you wear every day, without ever putting it on?

A beard

87. What is precious until it is broken, worth nothing afterwards, but can always be made anew when you wish it?

A promise

88. I am always right behind you, but look back and you will not be able to reach me. What am I?

The past

89. What question can nobody honestly reply “No” to?

Are you awake?

90. I have no head, but I often wear a cap. What am I?

A bottle

91. Someone installs a special device on a train, designed to bring it screeching to a halt before it reaches its destination. What is it?

The brakes

92. A man walks along an empty beach, seeing no signs of human life, for two hours. He keeps the ocean on his left the entire time, and eventually comes upon a set of footprints in the sand. They are the same size as his own. What has happened?

He has walked around the edge of a desert island

93. What has two wings, no feathers, sees through four eyes, and holds a hundred stomachs?

An aeroplane, with one co-pilot

94. Cut my skin and I won’t mind, but you might end up weeping. What am I?

An onion

95. What is something you might buy for dinner, but never dream of eating?

A knife and fork

96. You will always try to answer me, although I never answer you. What am I?

Your phone

97. What has no mouth, but always tells the truth?

A mirror

98. What will always help you to hold your head up, when you find yourself flat on your back?

A pillow

99. What kind of belt is worth more than the finest suit ever made?

A seatbelt

Trick Questions: Part 3

100. What three-letter word sounds like a letter it does not contain?


101. What has no light of its own, but can shine brightly through the blackest night?

The moon

102. What becomes easier to solve, the longer you put off getting to the heart of things?

A jigsaw puzzle

103. What has every explorer in history sailed towards, without ever being able to reach it?

The horizon

104. I can sleep quietly for centuries but, when I rise from my slumber, I become a waking nightmare for anyone close by. What am I?

A volcano

105. A park does not have one single tree, no playground, nowhere safe to walk a dog or to play football. Night and day it is filled with harsh electric light, and thick with the smell of petrol. Why does no-one complain?

It’s a car park

106. Pull us apart, then squeeze us together – there is no knot we cannot sever. What are we?

A pair of scissors

107. What kind of TV watches you?


108. What one thing could an interior designer add to any wall, that would immediately make the room feel more open?

A hole

109. What will you keep carrying around with you, until you are able to find it?

A splinter

110. When it’s time to eat, the larger I get the less I weigh. What am I?

Popcorn kernels

111. An elevator in a tall building, starting from the third floor, climbs eight storeys. After descending nine storeys again, then climbing seven storeys, it descends three storeys before climbing up seven storeys again. What floor is it on?

The thirteenth floor.

112. A trucker is driving some cargo across Canada. He starts in a busy metropolis and passes along a stretch of coastline, before turning inland. Crossing a medium-sized mountain range, he drives through heavy snow for three days straight. In the wee hours of the third night, he nearly gets lost near a frozen lake – but several hours later he is back on course, sunlight flickering at him through the trees as he heads straight toward a large forest. In less than 24 hours, he will have reached his destination. In which direction is he heading?

Eastward, towards the rising sun

113. What is something many wish they could get rid of, but nobody can live without?

Their age

114. Which four-letter word becomes longer if you add two letters to it?

All of them

115. A man refuses to wear a parachute, but still manages to jump from his plane without injury. How?

He waits until it has landed

116. How many letters are contained in the Arabic alphabet?

Seventeen, including the word “the”

117. What can you count on, when it all gets too much?

A calculator

118. Why is a bad lie like a window?

You can see straight through it

119. What would never be served for dinner, at a restaurant in South America?


120. Can you think of something that starts with an ‘E’ and then a ‘P,’ and contains thousands of letters?

An epic poem

121. Two soldiers marched off to war, fighting for opposite sides. Both died in the final battle, and one returned home alive and well. How is this possible?

‘Both’ was the name of one of the soldiers

122. What kind of line can be deadly, if you wait to reach the end of it?

A fishing line

123. Which four-legged animal is usually a stable sleeper?

A horse

124. In countries north of the equator, which day of the week will always have the most sun?


125. This warrior, if he loses his head, will cover all the land in darkness. What is he?

A knight

126. I glisten in the light. People wear me at the best of times, and also the worst; sometimes proudly, sometimes with shame. What am I?


127. Lucy has 5 eggs, Matthew will have 50 eggs, and Robert had 20. Who has the most eggs? 


128. Two nephews and two uncles went to a circus together. Each of them bought a ticket, but only three tickets were purchased. What happened?

There were three men – a nephew, his uncle, and that uncle’s uncle

129. Which is lighter, fifty pounds of feathers or fifty pounds in coppers?

£50 in copper coins would weigh less than 50lbs

130.  Two security guards arrive for work at the same time in the morning. They have both guarded the same bank vault for the past ten years, neither of them ever takes a sick day, but they have never once laid eyes on each other. How is this possible?

They guard the vault on different days

131. In our current system, which upcoming year is going to have eleven months?

All of them

132. Two men are caught in a sudden downpour, and are soaked from head to toe. Only one gets his shoes wet – why?

The other was barefoot

133. What should follow in this sequence: MTWTFS…

The letter ‘S’. They are the initial letters of each weekday

134. What do you have to leave behind, in order to make use of it?

Pencil lead

135. Beneath green skin, my heart is contained within a head. What am I?

A cabbage

136. Once you have given me to someone, you’ll find out whether you can keep me or not. What am I?

Your word

137. I have watched over you all your life, yet I am less than 30 days old. What am I?

The moon

138. What can carry a message over huge distances in seconds, without being seen by anyone?

An echo

139. I can be beaten, boiled or even burned, without ever once complaining. What am I?

An egg

140. What living thing can have eight limbs, a tough outer layer of skin, and is often found deep within forests?

A tree

141. It is quite normal to deliver me in a bowl. It would be unwise to try and eat me. What am I?

A cricket ball

142. What type of dress will you always come back to, no matter how tired of it you get?

Your address

143. You can flap and fly all day long, but you will never escape my grasp. What am I?

A flagpole

144. When Dennis was 12, his sister was half his age. Dennis is now 23. How old is his sister?  


145. What do dogs have that no other warm-blooded species on earth can ever have?


146. What has one sword, six legs, and a tail? 

A knight on horseback

147. In France, a cat is called “un chat”. In Germany, it would be “eine Katze”. What is a cat in the Antarctic?


148. My dog’s lead is five feet long. He is desperate to eat an ice cream someone has dropped eight feet away. How does he manage to reach it?

I am not holding the lead

149. Would you expect that a professional pole vaulter would be able to vault higher than a double-decker bus?

Yes – buses are unable to pole vault

150. How many playing cards does it take to finish building a house out of them, in the conventional way?

Only one, final card is needed to finish

More Riddles

55 Riddles for Teens // 136 Riddles for Adults // 55 Animal Riddles
75 Short Riddles // 40 Emoji Riddles // 172 Riddles for Kids
154 Trick Questions // 154 Funny Riddles // 73 Brain Teasers
82 Hard Riddles // 73 Dirty Riddles // 73 What Am I Riddles // 37 Egg Riddles

Tim Kelleher
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