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50 Tricky Riddles That Will Keep Even the Smartest Kids Guessing

The joyful pain of an impossible riddle.

If a funny riddle is like a brainier version of a corny joke, a hard riddle is like a challenging brainteaser that rewards kids with laughter in the end. In addition to teaching our kids empathy, cooperation, patience, and the like, we also want to engage their intellect. But that doesn’t mean giving them vocabulary quizzes at the dinner table — or relying exclusively on dumb jokes for laughs. Books, activities, and puzzles are all fun (emphasis on fun) ways to challenge kids and get them excited to problem-solve. But you don’t want to insult your kid’s intelligence by giving them puzzles that are too easy for them to solve. As they get older, you’ll have to work harder to keep them on their toes with ever-trickier riddles.

When brainstorming a hard riddle that you’re sure will stump your kid, you should also think about how their brain works. The best part of really hard riddles is that they reward every type of kid, depending on the riddle you give them: There are the number games for the math nerds, the wordplay for the book lovers, and the absurdist puzzles for the creative thinkers. Below are the best tricky riddles, with answers, that your kid may be able to figure out on their own…with enough patience.

  1. Riddle: What two things can you never have for breakfast?
    Answer: Lunch and Dinner
  2. Riddle: What is so fragile that saying its name breaks it?
    Answer: Silence.
  3. Riddle: What can run but never walks, has a mouth but never talks, has a head but never weeps, has a bed but never sleeps?
    Answer: A river
  4. Riddle: What can fill a room but takes up no space?
    Answer: Light
  5. Riddle: 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
  6. Riddle: What is the capital in France?
    Answer: The letter F is the only capital letter in France.
  7. Riddle: The more you take, the more you leave behind. What are they?
    Answer: Footsteps
  8. Riddle: 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
  9. Riddle: 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.
  10. Riddle: What breaks yet never falls, and what falls yet never breaks?
    Answer: Day and night
  11. Riddle: What goes through cities and fields, but never moves?
    Answer: A road
  12. Riddle: I am always hungry and will die if not fed, but whatever I touch will soon turn red. What am I?
    Answer: Fire
  13. Riddle: The person who makes it has no need of it; the person who buys it has no use for it. The person who uses it can neither see nor feel it. What is it?
    Answer: A coffin
  14. Riddle: 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
  15. Riddle: 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
  16. Riddle: I have lakes with no water, mountains with no stone and cities with no buildings. What am I?
    Answer: A map
  17. Riddle: 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
  18. Riddle: Mr. and Ms. Mustard have six daughters and each daughter has one brother. How many people are in the Mustard family?
    Answer: There are nine Mustards in the family. Since each daughter shares the same brother, there are six girls, one boy and Mr. and Ms. Mustard.
  19. Riddle: I am something people love or hate. I change people’s appearances and thoughts. If a person takes care of themself, I will go up even higher. Some people might want to try and hide me but I will show. No matter how hard people try I will never go down. What am I?
    Answer: Age
  20. Riddle: Only one color, but not one size,
    Stuck at the bottom, yet easily flies.
    Present in sun, but not in rain,
    Doing no harm, and feeling no pain.
    What is it?
    Answer: A shadow
  21. Riddle: Who is that with a neck and no head, two arms and no hands?
    Answer: A shirt
  22. Riddle: If eleven plus two equals one, what does nine plus five equal?
    11 o’clock plus 2 hours = 1 o’clock
    9 o’clock plus 5 hours = 2 o’clock
  23. Riddle: Can you write down eight eights so that they add up to one thousand?
    Answer: 888 + 88 + 8 + 8 + 8 = 1000
  24. Riddle: It can’t be seen, can’t be felt, can’t be heard, and can’t be smelt. It lies behind stars and under hills, And empty holes it fills. It comes first and follows after, Ends life, and kills laughter. What is it?
    Answer: The dark
  25. Riddle: What English word retains the same pronunciation, even after you take away four of its five letters?
    Answer: Queue
  26. Riddle: Three playing cards in a row. Can you name them with these clues? There is a two to the right of a king. A diamond will be found to the left of a spade. An ace is to the left of a heart. A heart is to the left of a spade. Now, identify all three cards
    Answer: Three playing cards in a row. Can you name them with these clues? There is a two to the right of a king. A diamond will be found to the left of a spade. An ace is to the left of a heart. A heart is to the left of a spade. Now, identify all three cards.
    Answer: Ace of Diamonds, King of Hearts, Two of Spades.
  27. Riddle: What is it that given one, you’ll have either two or none?
    Answer: A choice.
  28. Riddle: George, Helen, and Steve are drinking coffee. Bert, Karen, and Dave are drinking soda. Using logic, is Elizabeth drinking coffee or soda?
    Answer: Elizabeth is drinking coffee. The letter E appears twice in her name, as it does in the names of the others that are drinking coffee.
  29. Riddle: I have branches, yet I have no leaves, no trunk, and no fruit. What am I?
    Answer: A bank.
  30. Riddle: What has a head, a tail, is brown, and has no legs?
    Answer: A penny.
  31. Riddle: When I’m used, I’m useless. Once offered, soon rejected. In desperation, I’m oft expressed. What am I?
    Answer: An excuse.
  32. Riddle: I have four legs, but no hair. People ride me for hours, but don’t go anywhere. Without needing to be tugged or turned on, I always manage to be ready for work. What am I?
    Answer: A desk
  33. Riddle: 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.
  34. Riddle: When John was six years old he hammered a nail into his favorite tree to mark his height. Ten years later at age sixteen, John returned to see how much higher the nail was. If the tree grew by five centimeters each year, how much higher would the nail be?
    Answer: The nail would be at the same height since trees grow at their tops.
  35. Riddle: I am four times as old as my daughter. In 20 years time I shall be twice as old as her. How old are we now?
    Answer: I am 40 and my daughter is 10.
  36. Riddle: There was a man who was born before his father, killed his mother, and married his sister. Yet, there was nothing wrong with what he had done. Why?
    Answer: His father was in front of him when he was born, therefore he was born before him. His mother died while giving birth to him. Finally, he grew up to be a minister and married his sister at her ceremony.
  37. Riddle: Lily is a lilypad in a small pond. Lily doubles her size each day, On the 20th day she covers the whole pond. On what day was Lily half the size of the pond?
    Answer: Day 19, it’s not 10 because on day 20 she doubled from day 19, so 19 must be half the size of the pond.
  38. Riddle: What common English verb becomes its own past tense by rearranging its letters?
    Answer: Eat and ate.
  39. Riddle: When asked how old she was, Suzie replied, “In two years I will be twice as old as I was five years ago.” How old is she?
    Answer: She’s 12.
  40. Riddle: Lighter than what I am made of, More of me is hidden Than is seen. What am I?
    Answer: An iceberg.
  41. Riddle: 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.
  42. Riddle: The man who bought it doesn’t want it for himself. The man who buys it doesn’t buy it for himself. And the man who needs it doesn’t know he needs it. What is it?
    Answer: A coffin.
  43. Riddle: I have cities, but no houses. I have mountains, but no trees. I have water, but no fish. What am I?
    Answer: A map.
  44. Riddle: 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.
  45. Riddle: First, think of the color of the clouds. Next, think of the color of snow. Now, think of the color of a bright, full moon. Now, answer quickly: what do cows drink?
    Answer: Water
  46. Riddle: Different lights do make me strange, thus into different sizes I will change. What am I
    Answer: I am the pupil of an eye.
  47. Riddle: What has a tail and a head but no body?
    Answer: A coin
  48. Riddle: I am an odd number. Take away a letter and I become even. What number am I?
    Answer: Seven
  49. Riddle: If a red house is made of red bricks, and a yellow house is made of yellow bricks, what is a greenhouse made of?
    Answer: All greenhouses are made of glass.
  50. Riddle: What can never be put in a saucepan?
    Answer: Its lid.