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Hard riddles

Riddles that most adults need a hint to solve. Every one still has a single answer that fits all the clues.

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How to play a riddle game

1. One person reads the riddle. Reading it twice is allowed.
2. Everyone guesses out loud, or teams write one answer down.
3. Reveal the answer. The first correct guess scores a point, and the winner reads the next riddle.

Updated November 2026.

1. What gets whiter the dirtier it gets? Answer: A chalkboard (or blackboard)
2. The more of them you take, the more you leave behind. What are they? Answer: Footsteps
3. What is so fragile that saying its name breaks it? Answer: Silence
4. Where does Friday come before Thursday? Answer: In the dictionary
5. What tastes better than it smells? Answer: Your tongue
6. What has thirteen hearts but no other organs? Answer: A deck of cards
7. What is black when you buy it, red when you use it and gray when you throw it away? Answer: Charcoal
8. Spelled forward, I'm heavy. Spelled backward, I'm not. What word am I? Answer: Ton
9. What five-letter word gets shorter when you add two letters to it? Answer: Short
10. What has a foot on each end and a third foot in the middle? Answer: A yardstick
11. What walks on four legs in the morning, two at noon and three in the evening? Answer: A person
12. What is harder to catch the faster you run? Answer: Your breath
13. What goes around and around the wood but never goes into the wood? Answer: The bark of a tree
14. What three different positive whole numbers give the same answer whether you add them or multiply them? Answer: One, two and three
15. Two mothers and two daughters each order a burger. Only three burgers come, and nobody goes without. How? Answer: They are a grandmother, a mother and a daughter
16. How many times can you subtract five from twenty-five? Answer: Once. After that it's twenty.
17. The doctor hands you three pills and says to take one every half hour. How long until they're gone? Answer: One hour
18. Before Mount Everest was discovered, what was the tallest mountain on Earth? Answer: Mount Everest
19. How far can a dog run into the woods? Answer: Halfway. After that it's running out.
20. Pointing at a photo, a man says: I have no brothers or sisters, but that man's father is my father's son. Who is in the photo? Answer: His son
21. A ladder hangs off a ship with its bottom rung just touching the water. The tide rises three feet. How many rungs are under water now? Answer: None. The ship rises with the tide.
22. You have two coins worth thirty cents together, and one of them is not a nickel. What are they? Answer: A quarter and a nickel. The quarter is the one that isn't a nickel.
23. What is the only number whose letters are in alphabetical order when you spell it out? Answer: Forty
24. Which number has exactly as many letters as its own value? Answer: Four
25. What is thirty divided by one half, plus ten? Answer: Seventy
26. A woman has seven daughters, and each daughter has one brother. How many children does she have? Answer: Eight
27. What can you put between a five and a six to get a number bigger than five and smaller than six? Answer: A decimal point
28. When Jo was six, her sister was half her age. Jo is forty now. How old is her sister? Answer: Thirty-seven
29. A snail is at the bottom of a ten-foot well. Each day it climbs three feet, and each night it slides back two. On which day does it get out? Answer: Day eight
30. A pen and a notebook cost $1.10 together. The notebook costs a dollar more than the pen. How much is the pen? Answer: Five cents
31. A patch of clover doubles in size every day and covers the whole lawn on day thirty. On which day did it cover half the lawn? Answer: Day twenty-nine
32. If five machines take five minutes to make five toys, how long do a hundred machines take to make a hundred toys? Answer: Five minutes
33. What letter comes next: O, T, T, F, F, S, S? Answer: E, for eight
34. A man shaves a dozen times a day and still has a full beard. How? Answer: He's a barber
35. A cowboy rides into town on Friday, stays three nights and rides out on Friday. How? Answer: His horse is named Friday
36. A truck driver goes the wrong way down a one-way street, right past a police officer, and doesn't get a ticket. Why? Answer: He was walking
37. How can you drop a raw egg onto a concrete floor without cracking it? Answer: Easily. Concrete floors are very hard to crack.
38. The butcher is six feet tall and wears size twelve shoes. What does he weigh? Answer: Meat
39. What has six faces and twenty-one eyes but can't see? Answer: A die
40. What can be cracked, made, told and played? Answer: A joke
41. What can be driven without wheels and sliced without a knife? Answer: A golf ball
42. I'm dug out of the ground and shut inside a wooden case that I never leave, yet nearly everyone has used me. What am I? Answer: Pencil lead (graphite)
43. What word sounds exactly the same after you take away four of its five letters? Answer: Queue
44. What seven-letter word has hundreds of letters in it? Answer: Mailbox
45. What goes through a door but never comes in or goes out? Answer: A keyhole
46. What can you swallow by the glass that can also swallow you whole? Answer: Water
47. Throw me off a rooftop and I'll be fine. Drop me in a puddle and I'm ruined. What am I? Answer: A sheet of paper
48. What has room for ten fingers but can only be filled by empty hands? Answer: A pair of gloves
49. What goes in dry, comes out wet, and the longer it stays in, the stronger the drink gets? Answer: A tea bag
50. What connects two people but touches only one? Answer: A wedding ring
51. What can you steal in front of thousands of people, with an umpire watching, and get cheered for it? Answer: A base
52. What kind of running means you'll be walking? Answer: Running out of gas
53. What kind of stones are never found in the ocean? Answer: Dry ones
54. What is the difference between a jeweler and a jailer? Answer: One sells watches and the other watches cells
55. What is the difference between a cat and a comma? Answer: One has claws at the end of its paws. The other is a pause at the end of a clause.
56. What is the difference between a teacher and a train conductor? Answer: One trains minds and the other minds trains
57. I saw a cruise ship packed with people, yet there wasn't a single person on board. How? Answer: They were all married
58. My grandfather is only six years older than my father. How is that possible? Answer: He is my mother's father
59. How many birthdays does a ninety-year-old have? Answer: One. The rest are anniversaries.
60. What is bought by the yard and worn by the foot? Answer: Carpet
61. What was tomorrow yesterday and will be yesterday tomorrow? Answer: Today
62. What falls every evening without breaking, and what breaks every morning without falling? Answer: Night and day
63. What do you get twice for free but have to pay for the third time? Answer: Teeth
64. What can you keep only after you've given it to someone? Answer: Your word (or a promise)
65. What do you break every morning without making a sound? Answer: Your fast
66. What has a crown without being a king and a root without being a plant? Answer: A tooth
67. Which two parts of your body share their names with a tree and a fish? Answer: Your palm and your sole
68. What state is round at both ends and high in the middle? Answer: Ohio
69. What is the difference between ignorance and apathy? Answer: I don't know and I don't care
70. What is the difference between a badly dressed man on a tricycle and a well dressed man on a bicycle? Answer: Attire
71. At a meeting, what can run for pages and still be only minutes? Answer: The minutes
72. What bar serves no drinks and can take years to pass? Answer: The bar exam
73. What has thirty years of interest and no curiosity at all? Answer: A mortgage
74. What do you nurse the morning after a big night, though it will never grow up? Answer: A hangover
75. How can a flight land earlier than it took off? Answer: By crossing time zones
76. How many times do you write the digit nine when you count from one to a hundred? Answer: Twenty
77. Turn me on my side and I'm everything. Cut me in half and I'm nothing. What number am I? Answer: Eight
78. How many bricks does it take to finish a brick house? Answer: One: the last one

Tips for a better game

• Offer one hint for the hard riddles, such as the first letter of the answer.
• With kids, let them read the riddles to the adults. They enjoy knowing the answer.
• Start a round with two easy riddles so that everyone has scored before the hard ones.

Questions people ask

What are some good hard riddles?

Five from this list: What has thirteen hearts but no other organs? (A deck of cards) You have two coins worth thirty cents together, and one of them is not a nickel. What are they? (A quarter and a nickel. The quarter is the one that isn't a nickel.) How can you drop a raw egg onto a concrete floor without cracking it? (Easily. Concrete floors are very hard to crack.) What kind of stones are never found in the ocean? (Dry ones) What state is round at both ends and high in the middle? (Ohio)

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