Flexible Thinking + 166 riddles


A good education can provide the foundation for success in life. In addition to the basics, such as numeracy and literacy, there are key skills that help children and adults navigate complex situations and make better decisions. Flexible thinking is a crucial element for future success.


One technique we learn early on is to group things. Our ability to recognize patterns develops quickly. As a result, the game, 'One of these things is not like the other,' is fun because it is easy. Over time we link more and more situations together. Patterned thinking reduces the amount of thought we need to analyze problems and quickly make decisions. The disadvantage is that we become reliant on these patterns and the assumptions associated with our groupings. Our thinking becomes constrained to the point where we cannot think of outcomes and solutions that do not fit previously established patterns.

Flexible thinking helps us to think beyond our patterns and recognize our assumptions. Similar to numeracy and literacy, flexible thinking takes practice. Escape rooms provide a fun way to develop flexible thinking. Riddles, clues, and puzzles rely on our well-established patterns to make escape rooms challenging to solve, but in hindsight the answers are easy. Awesome Escape Rooms 4 Kids offer online escape rooms that allow children to develop their flexible thinking through escaping weekly. You can find more information on our programs at this link.

In the meantime, below is a growing list of riddles that children and adults can use to start developing their flexible thinking.   



1. It’s shorter than the rest, but when you’re happy, you raise it up like it’s the best. What is it?

Answer: A thumb.


2. One knight, a ninja, and a pirate are on a boat. The boat crashes. The pirate jumps of first, the ninja jumps off second, and who jumps off third?

Answer: The knight.



3. You can see me in water, but I never get wet. What am I?

Answer: A reflection.


4. Which part of a boat, does a shopaholic like the most?

Answer: A sail.


5. Take away the whole and some still remain. What is it?

Answer: The word “wholesome.”


6. What has to be broken before you can use it?

Answer: A egg.


7.The more you take, the more you leave behind. What am I?

Answer: Fingerprints.


8. I’m tall when I’m young, and I’m short when I’m old. What am I?
Answer: A candle.


9. Where does today come before yesterday?

Answer: The dictionary.


10. What question can you never answer yes to?

Answer: Are you asleep yet?


11. Forward I am heavy, but backward I am not. What am I?

Answer: Forward I am ton, backward I am not.


12. A rooster lays an egg at the very top of a slanted roof. Which side is the egg going to roll off on?

Answer: Neither, roosters don’t lay eggs.


13. There’s a one-story house in which everything is yellow. Yellow walls, yellow doors, yellow furniture. What color are the stairs?
Answer: There aren’t any – it’s a one-story house.


14. A word I know, six letters it contains, remove one letter, and twelve remains. What am I?

Answer: Dozens.


15. What can you break, even if you never pick it up or touch it?
Answer: A promise.


16. What month of the year has 28 days?

Answer: All of them.


17. A barrel of water weighs 60 pounds. What must you put in it for it to weigh 40 pounds?

Answer: A hole.


18. What is always in front of you but can’t be seen?

Answer: The future.


19. How do football players stay cool during a game?

Answer: They stand next to the fans.


20. What goes up but never comes down?

Answer: Your age.


21. What word looks the same upside down and backward?

Answer: Swims.


22. A man who was outside in the rain without an umbrella or hat didn’t get a single hair on his head wet. Why?

Answer: He was bald.


23. You see a sail boat filled with people, yet there isn’t a single person on board. How is that possible?
Answer: All the people on the boat are married.


24. What invention lets you look right through a wall?

Answer: A window.


25. David’s parents have three sons: Snap, Crackle, and what’s the name of the third son?
Answer: David.


26. What has ten letters and starts with gas?

Answer: An automobile.


27. What is full of holes but still holds water?

Answer: A sponge.


28. You walk into a room that contains a match, a kerosene lamp, a candle and a fireplace. What would you light first?

Answer: The match.


29. What can’t be put in a saucepan?

Answer: A staircase.


30. I follow you all the time and copy your every move, but you can’t touch me or catch me. What am I?

Answer: Your shadow.


31. What gets wet while drying?

Answer: A towel.


32. How can you drop a raw egg on a concrete floor from a 10 feet high balcony without breaking it?

Answer: Concrete floors are hard to crack.


33. What can you keep after giving to someone?

Answer: Your word.


34. I’m light as a feather, yet the strongest person can’t hold me for five minutes. What am I?
Answer: Your breath.


35. What can you hold in your left hand but not in your right?
Answer: Your right elbow.


36. A man dies of old age on his 25th birthday. How is this possible?

Answer: He was born on February 29.


37. I’m found in socks, scarves and mittens; and often in the paws of playful kittens. What am I?
Answer: Yarn.


38. What can’t talk but will reply when spoken to?
Answer: An echo.


39. If you’re running in a race and you pass the person in second place, what place are you in?
Answer: A second place.


40. I have branches, but no fruit, trunk or leaves. What am I?
Answer: A bank.


41. What gets bigger when more is taken away?

Answer: A hole.


42. If you’ve got me, you want to share me; if you share me, you haven’t kept me. What am I?
Answer: A secret.


43. What is black when it’s clean and white when it’s dirty?

Answer: A chalkboard.


44. The more of this there is, the less you see. What is it?

Answer: Darkness.


45. It belongs to you, but other people use it more than you do. What is it?
Answer: Your name.


46. What has many keys but can’t open a single lock?

Answer: A piano.


47. It is an insect, and the first part of its name is the name of another insect. What is it?

Answer: Beetle.


48. Which of the following words don't belong in the group and why? CORSET, COSTER, SECTOR, ESCORT, COURTS

Answer: Courts. All of the others are anagrams of each other.


49. What has four fingers and thumb, but it is not living?

Answer: A glove.


51. If eleven plus two equals one, what does nine plus five equal?

Answer: 11 o'clock plus 2 hours = 1 o'clock. 9 o'clock plus 5 hours = 2 o'clock.


52. What is it that given one, you'll have either two or none?

Answer: A choice.


53. Can you write down eight eights so that they add up to one thousand?

Answer: 888 + 88 + 8 + 8 + 8 = 1000.


54. What can’t be burned in a fire nor drowned in the water?

Answer: Ice. It melts instead of burning in a fire and it floats in water.


55. What English word retains the same pronunciation, even after you take away four of its five letters?

Answer: Queue.

56. Where do monkeys get their exercise?
Answer: The jungle gym.

57. If the red house is on the right and the blue house is on the left, where is the white house?
Answer: Washington D.C.

58. Where can you find cities, towns, shops, and streets but no people?”

Answer: A map.


59. What is so fragile that saying its name breaks it?”

Answer: Silence.


60. What has a bottom at the top?”

Answer: Your legs.

61. I am the beginning of everything, the end of everywhere. I’m the beginning of eternity, the end of time and space. What am I?
Answer: The letter “e.”

62. Forward I am heavy, but backward I am not. What am I?
Answer: The word “not.”

63. When you look for something, why is it always in the last place you look? 

Answer: Because when you find it, you stop looking.


64. A cowboy rode into town on Friday.  He stayed in town for three days and rode out on Friday.  How was that possible? 

Answer: Friday was the name of his horse.


65. Railroad.  Can you spell that without any “r’s”? 

Answer: That.


66. What has a face and two hands, but no arms or legs? 

Answer: A clock.

67. Two fathers and two sons are in a car, yet there are only three people in the car. How?
Answer: They are a grandfather, father and son.

68. What has one eye, but can’t see?
Answer: A needle.

69. What’s black and white and read all over?”

Answer: A newspaper.


70. Lives in winter, dies in summer, and grows with its roots upward.  What is it? 

Answer: An icicle.


71. How can a man go 8 days without sleep? 

Answer: He only sleeps at night.

72. What does man love more than life, hate more than death or mortal strife; that which contented men desire; the poor have, the rich require; the miser spends, the spendthrift saves, and all men carry to their graves?
Answer: Nothing.

73. People make me, save me, change me, raise me. What am I?
Answer: Money


74. The day before yesterday I was 21, and next year I will be 24. When is my birthday?
Answer: December 31; today is January 1.


75. Which is heavier, a pound of bricks or a pound of feathers? 

Answer: The same. A pound is a pound!


76. I have no life, but I can die. What am I?”

Answer: A battery.


77. Can you name three consecutive days without using the words Wednesday, Friday, and Sunday? 

Answer: Yesterday, today, and tomorrow.

78. What is 3/7 chicken, 2/3 cat and 2/4 goat?
Answer: Chicago.

79. Timmy’s mother had three children.  The first was named April, the next was named May.  What was the name of the third child? 

Answer: Timmy.


80. Two in a corner, one in a room, zero in a house, but one in a shelter. What is it?
Answer: The letter “r.”


81. What kind of coat can only be put on when wet? 

Answer: A coat of paint.


82. A man looks at a painting in a museum and says, “Brothers and sisters I have none, but that man’s father is my father’s son.” Who is in the painting?
Answer: The man’s son


83. What occurs once in a minute, twice in a moment, and never in one thousand years? 

Answer: The letter M.


84. Mary has four daughters, and each of her daughters has a brother. How many children does Mary have?”

Answer: Five. Each daughter has the same single brother.


85. What would you find in the middle of Toronto?
Answer: The letter “o.”


86. What has three feet but cannot walk? 

Answer: A yardstick.


87. What runs, but never walks, often murmurs – never talks, has a bed but never sleeps, has a mouth but never eats? 

Answer: A river.

88. I am a word of letters three; add two and fewer there will be. What word am I?
Answer: Few.

89. With pointed fangs I sit and wait; with piercing force I crunch out fate; grabbing victims, proclaiming might; physically joining with a single bite. What am I?
Answer: A stapler.

90. What gets sharper the more you use it? 

Answer: Your brain.

91. What 4-letter word can be written forward, backward or upside down, and can still be read from left to right?
Answer: noon.

92. You see me once in June, twice in November and not at all in May. What am I?
Answer: The letter “e.”

93. What can you catch but not throw? 

Answer: A cold.


94. They come out at night without being called, and are lost in the day without being stolen.  What are they? 

Answer: Stars.

95. I turn once, what is out will not get in. I turn again, what is in will not get out. What am I?
Answer: A key.

96. A man calls his dog from the opposite side of the river. The dog crosses the river without getting wet, and without using a bridge or boat. How?
Answer: The river was frozen.

97. Two in front, two in behind, and one in the middle.  How many are there? 

Answer: Three. (212).

98. A little girl goes to the store and buys one dozen eggs. As she is going home, all but three break. How many eggs are left unbroken?
Answer: Three.

99. What word of five letters has one left when two are removed?
Answer: Stone.


100. What word is spelled wrong in every dictionary?

Answer: The word “wrong.”


101. What has four wheels and flies?”

Answer: A garbage truck.


102. What is easy to get into, but hard to get out of?

Answer: Trouble!


103. What word contains 26 letters, but only three syllables?

Answer: Alphabet.


104. A girl fell off a long staircase. She wasn’t hurt. Why?

Answer: She fell off the bottom step.


105. What building has thousands of stories?

Answer: The library.

106. I am a word that begins with the letter “i.” If you add the letter “a” to me, I become a new word with a different meaning, but that sounds exactly the same. What word am I?
Answer: Isle (add “a” to make “aisle”).

107. What has a neck but no head?

Answer: A bottle.


108. A bat and a ball cost $1.10. The bat costs $1.00 more than the ball. How much does the ball cost? 

Answer: 5 cents.


109.What are two things you can NEVER eat for breakfast?

Answer: Lunch and dinner.


110. Which weighs more: a pound of feathers or a pound of bricks?”

Answer: They weigh the same.


111. What goes up and down but never moves?

Answer: The temperature.

112. A man describes his daughters, saying, “They are all blonde, but two; all brunette but two; and all redheaded but two.” How many daughters does he have?
Answer: Three: A blonde, a brunette and a redhead.

113. What can fill a room but takes up no space?
Answer: Light.

114. What three numbers, none of which is zero, give the same result whether they’re added or multiplied?
Answer: One, two and three.

115. What has many needles, but doesn’t sew?
Answer: A Christmas tree.

116. What kind of band never plays music?
Answer: A rubber band.

117. The more you take, the more you leave behind? What are they? Answer: Footprints.

If you drop me I’m sure to crack, but give me a smile and I’ll always smile back. What am I?
Answer: A mirror.

118. I have no eyes, no ears, and legs, and yet I help move the earth. What am I? 

Answer: An earthworm.

119. Three doctors said that Bill was their brother. Bill says he has no brothers. How many brothers does Bill actually have?
Answer: None. He has three sisters.


120. What word in the English language does the following: The first two letters signify a male, the first three letters signify a female, the first four letters signify a great, while the entire world signifies a great woman. What is the word?
Answer: Heroine.

121. If there are three cookies and you take away two, how many do you have?

Answer: If you take two, you have two.


122. What do dogs have that no other animal has?

Answer: Puppies.


123. What has one head, one foot, and four legs?”

Answer: A bed.


124. Give me food, and I will live. Give me water, and I will die. What am I?

Answer: Fire.


125. What goes through cities and fields, but never moves?
Answer: A road


126. First, I threw away the outside and cooked the inside. Then I ate the outside and threw away the inside. What did I eat? 

Answer: Corn on the cob.


127. If there are three apples and you take away two, how many apples do you have?
Answer: You have two apples.


128. What has many teeth, but can’t bite?
Answer: A comb.


129. What do kids play when they can’t play with a phone?
Answer: Board games.


130. What do you call two monkeys sharing an Amazon account?
Answer: Prime mates.


131. What do birds give out on Halloween?

Answer: Tweets.


132. What is cut on a table, but is never eaten?
Answer: A deck of cards.


133. What runs all around a backyard, yet never moves?
Answer: A fence.


134. Why was the weightlifter upset?
Answer: She worked with dumbbells.


135. Why are teddy bears never hungry?
Answer: They’re always stuffed.


136. What begins with an E but only has one letter in it?”

Answer: An envelope.


137. What’s Thanos’ favorite app to talk to friends?
Answer: Snap chat.


138. What event do spiders love to attend?
Answer: Webbings.


139. What did one math book say to the other?
Answer: I’ve got so many problems.


140. I am an odd number. Take away a letter and I become even. What number am I?”

Answer: Seven.


141. Why can’t you ever tell a joke around glass?
Answer: It could crack up.


142. What breaks yet never falls, and what falls yet never breaks?
Answer: Day, and night.


143. What has words, but never speaks?
Answer: A book.

144. What can travel all around the world without leaving its corner?
Answer: A stamp.

145. How do you know when a bike is thinking?
Answer: You can see its wheels turning.

146. A girl has as many brothers as sisters, but each brother has only half as many brothers as sisters. How many brothers and sisters are there in the family?
Answer: Four sisters and three brothers.

147. How did Benjamin Franklin feel when he discovered electricity?
Answer: Shocked.


148. Why did the daddy rabbit go to the barber?
Answer: He had a lot of little hares.

149. What has a head and a tail but no body?
Answer: A coin


150. What kind of shoes do private investigators wear?
Answer: Sneakers.


151. How do billboards talk?
Answer: Sign language.


152. What game does the sky love to play?
Answer: Twister.


153. Why do we never tell jokes about pizza?
Answer: They’re too cheesy.


154. Where does one wall meet the other wall?
Answer: On the corner


155. What kind of lunch do moms never prepare in the morning?
Answer: Their own.


156. What is the end of everything?
Answer: The letter “g.”


157. Did you hear the joke about the roof?
Answer: Never mind, it’s over your head.


158. What tastes better than it smells?
Answer: Your tongue


159. What time is it when people are throwing pieces of bread at your head?
Answer: Time to duck.


160. What do you do if someone rolls their eyes at you?
Answer: Roll them back.


161. What’s the difference between a guitar and a fish?
Answer: You can tune a guitar but you can’t tunafish.

162. What did the sink say to the potty?
Answer: You look flushed.


163. What’s a snake’s strongest subject in school?
Answer: History.


164. Why did the God of Thunder need to stretch his muscles so much when he was a kid?
Answer: He was a little Thor.


165. What has lots of eyes, but can’t see?
Answer: A potato.

166. If two’s company, and three’s a crowd, what are four and five?
Answer: Nine.