Tricky Riddles with Answers
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Tricky riddles play dirty. The obvious answer is almost always wrong, and that's the point. They are ordered so the trick lands, graded by how well the trap hides, and every reveal names the exact misdirection that caught you. Slow down, question your first guess, then tap to see if you got played.
Tricky riddles trip you on the assumption you brought with you
Almost nothing on this page is false, and that is the whole trick. The riddle states a few plain facts, and the reader adds one more without noticing: that the surgeon is a man, that the plane is in the air, that a rooster can lay an egg. When the first clue lands, treat the question as a witness statement. Read it twice, then write down every fact you know that the sentence did not actually say. The answer is usually hiding in that list.
The second habit covers the number riddles. A number in a tricky riddle is often a decoy placed to start arithmetic the wording never asked for. Seventeen sheep sits there to tempt a subtraction; three eggs in one pot invites a multiplication; five frogs and one that decides to jump makes you count before you check whether anything happened. Ask what the number is for before you touch it, and reread the verb next to it.
This is also where the page ends and the hard riddles begin. A tricky riddle gives you two or three clues and one assumption to drop, and once it drops, the answer is plain. A hard riddle stacks contradictions and second senses on top of each other, so dropping one assumption only opens the next layer. Solvers who like the logic side of this page will find the same habit stretched over longer scenes in the logic riddles.
- Riddle 2: most people say Eight sheep. Seventeen minus nine is the arithmetic the riddle wants you to do. The word but blocks it: all but nine died means every sheep except nine died, so nine is the count of the living, not the dead.
- Riddle 22: most people say His stepfather. A second father is the fix people reach for once they decide the surgeon must be a man. Nothing in the riddle says so. The boy has a mother, and she can be the surgeon.
- Riddle 30: most people say Four frogs. Subtracting the frog that decides to jump feels automatic. Decides is the word that stops it: the frog has made up its mind and nothing more, and a frog still thinking about it is still sitting on the log.
- Riddle 60: most people say Three rungs. One foot an hour for three hours looks like three rungs underwater. The boat is the word to reread: a boat floats, so the whole ladder rises with the tide and the bottom rung stays where it was, touching the surface.
Before you answer a tricky riddle, name the fact you added that the sentence never said.
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1. What can you break without touching it, dropping it, or even seeing it? Easy
Most people first say: Someone's heart
Show answer
A promise.
Break carries two senses, and the riddle leans on the one about shattering glass. Its other sense, failing to keep your word, needs no hands, no fall and no object in sight.
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2. A farmer had 17 sheep. All but 9 died. How many sheep are left? Easy
Most people first say: Eight sheep
Show answer
Nine. All but nine means nine survived.
Seventeen sits there to tempt a subtraction. The phrase all but nine names the ones that lived, so the first number never enters the arithmetic at all.
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3. One egg takes ten minutes to hard boil. How long does it take to hard boil three eggs in the same pot of water? Easy
Most people first say: Thirty minutes
Show answer
Ten minutes. All three eggs cook at the same time.
Three is placed to invite multiplication the question never asks for. Eggs sharing one pot cook side by side, so the cooking time stays the time for a single egg.
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4. A plane crashes right on the border between two countries. Where do they bury the survivors? Easy
Most people first say: Right on the border
Show answer
Nowhere. You do not bury survivors.
Survivors is the word skipped in the rush to pick a country. The question asks where to bury people who lived through the crash, and the living get no grave.
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5. A rooster lays an egg on the very top of a slanted roof. Which side does the egg roll down? Easy
Most people first say: The steeper side
Show answer
Neither. Roosters do not lay eggs.
A roof, a slope and a tumbling egg keep your eyes on physics. The dropped assumption is about the bird: a rooster is a male chicken, and hens do the laying.
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6. What kind of dress can never be worn? Easy
Show answer
An address.
Said aloud, a dress and address are the same two syllables, and the question exploits that ear trick. One is cloth you wear, the other is where the mail goes.
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7. An electric train is heading north at 100 miles per hour with a strong wind blowing from the west. Which way does the smoke blow? Easy
Most people first say: Toward the east
Show answer
There is no smoke. Electric trains do not produce any.
Speed, heading and wind direction are all decoys for a vector sum. Electric is the word to weigh: a motor drawing power from a wire burns nothing, so there is no smoke to push.
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8. Why can a man living in New York not be buried in Chicago? Easy
Most people first say: State burial laws
Show answer
Because he is still living. You cannot bury a living man.
In New York is an address, so living reads as where he resides, the way someone lives in Brooklyn. Read living as the opposite of dead and the geography stops mattering, since a breathing man is buried nowhere.
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9. How many bricks does it take to complete a brick building? Easy
Most people first say: Thousands of bricks
Show answer
Just one. The last brick completes it.
Complete means finish, not build. Every brick before the last leaves the building unfinished, so however tall the wall, one brick does the completing.
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10. What disappears the moment you stand up? Easy
Most people first say: Your shadow
Show answer
Your lap.
Disappears sends you after a thing with substance, a shadow or a light. The riddle wants a shape made by posture: the flat top of your thighs exists only while you sit.
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11. Which word is always spelled incorrectly in every dictionary? Easy
Show answer
The word incorrectly.
Spelled incorrectly reads as a mistake to hunt for, so you scan for a misprinted entry. The word names itself: the dictionary spells incorrectly as incorrectly, which is the only way to spell it.
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12. Railroad crossing, watch out for cars. Can you spell that without any Rs? Easy
Most people first say: It cannot be done
Show answer
T-H-A-T. The word that has no R in it.
The railroad line floods your ears with Rs, but you only need to spell the small word that, which has none.
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13. What kind of tree can you carry in your hand? Easy
Most people first say: A bonsai tree
Show answer
A palm.
Tree pins the picture to a trunk and branches, while carry hints at a potted plant. Palm names both a tropical tree and the flat inside of a hand, and the hand is the carry.
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14. Which building has the most stories? Easy
Most people first say: A skyscraper
Show answer
The library. Every shelf is full of them.
You read stories as floors and picture a skyscraper, but a library holds the most stories as in tales on its shelves.
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15. What kind of coat is best put on wet? Easy
Most people first say: A raincoat
Show answer
A coat of paint.
Wearing a wet garment is a miserable idea, and coat keeps the mind on clothes. The other coat is a layer brushed onto a wall, and that kind goes on wet or not at all.
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16. Ten children walk to school huddled under one small umbrella, yet none of them gets wet. How is that possible? Easy
Most people first say: They squeeze in tight
Show answer
It is not raining.
Ten kids under one umbrella starts a geometry problem about shoulders and elbows. Nobody said it was raining; the umbrella might be shade, a toy or a prop, and dry ground keeps everyone dry.
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17. What goes up every year but never comes back down? Easy
Show answer
Your age.
Goes up invites a picture of something climbing into the sky, a balloon or smoke. Up also means increases, and one number attached to you grows by exactly one each birthday and never drops back.
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18. How do you make the number one disappear? Easy
Most people first say: Subtract one
Show answer
Add the letter G in front of it and it is gone.
Disappear points at arithmetic, but the number here is the written word ONE. A single letter placed before it turns the word into GONE, and the trick is spelling, not math.
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19. You are running a long race, and just before the finish line you overtake the runner in second place. What position are you in now? Easy
Most people first say: First place
Show answer
Second place. You took the spot of the person you passed, not the leader's.
You feel like passing someone moves you up toward first, but you take the passed runner's second-place spot, not the leader's.
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20. What invention lets you look straight through a solid wall? Easy
Most people first say: X-ray glasses
Show answer
A window.
Invention and solid wall together promise something high tech. Nothing in the wording rules out the oldest fix of all: cut an opening and fill it with glass.
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21. What kind of cup cannot hold any water? Easy
Most people first say: A cup with a hole
Show answer
A cupcake.
Cup is read as a vessel for drinking, so a leaky one comes first. The word also labels a small baked cake, and that kind holds frosting instead of water.
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22. A father and his son are in a car accident. The boy is rushed into surgery, but the surgeon says: I cannot operate on him, he is my son. How can that be? Easy
Most people first say: His stepfather
Show answer
The surgeon is his mother.
The riddle never says the surgeon is a man; that detail is supplied by the reader. Drop it and there is no puzzle left, since a boy has two parents and either one can be a surgeon.
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23. How many animals of each kind did Moses take onto the ark? Easy
Most people first say: Two of each kind
Show answer
None. It was Noah who built the ark, not Moses.
Moses slips past because the question sounds like a Sunday school quiz and the counting starts before the name is checked. The ark belonged to Noah, so a Moses question has no animals in it.
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24. You walk into a dark room holding one match. Inside there is a candle, an oil lamp, and a fireplace. Which do you light first? Easy
Most people first say: The candle
Show answer
The match. Nothing else can be lit before it.
Three things that can burn make a menu, and picking one feels like the whole task. The unlit match in your hand has to burn before anything else does, and the question asked what you light first.
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25. Which is correct: the yolk of the egg is white, or the yolk of the egg are white? Easy
Most people first say: The yolk is, singular
Show answer
Neither. Yolks are yellow.
Two grammar options invite a debate about singular and plural. Both sentences fail on the same fact: a yolk is yellow, and the egg white is the part that is white.
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26. A man dressed all in black walks down a country lane at night. A black car with its headlights off comes straight at him, yet the driver swerves in time. How did the driver see him? Easy
Most people first say: A full moon
Show answer
It was daytime. Nothing in the story said it was night for the driver, only that the man wore black.
Black clothes and unlit headlights pile into a picture of pitch dark, and night in the first sentence seals it. The answer hangs on when the car comes by: later, in daylight, when a driver needs no lamps to see a walker.
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27. What can you serve but never eat? Easy
Show answer
A tennis ball.
Serve is heard as bringing food to a table, so every guess is something on a plate. In tennis the word means the opening hit, and the thing served is felt and rubber.
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28. Which side of a cat has the most fur? Easy
Most people first say: The left side
Show answer
The outside.
Side sets up a choice between left and right, as if fur could favor one flank. Drop the two-way frame: a cat has an inside and an outside, and every hair is on the outer one.
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29. Is it legal for a man to marry his widow's sister? Easy
Most people first say: Yes, it is legal
Show answer
It does not matter. If his wife is a widow, the man is dead.
Legal pulls you into marriage law and family ties. Widow is the word to stop on: a woman is a widow only after her husband dies, so the man in question is no longer around to marry anyone.
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30. Five frogs sit on a log and one of them decides to jump into the pond. How many frogs are left on the log? Easy
Most people first say: Four frogs
Show answer
Five. Deciding to jump is not the same as jumping.
Two numbers are placed so that subtraction feels automatic. Decides is the verb to catch: making up your mind to jump moves nobody, and the log holds the same crowd it started with.
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31. A man goes out for a walk in heavy rain with no umbrella, no hat, and no hood, yet not a single hair on his head gets wet. How? Easy
Most people first say: He walked under awnings
Show answer
He is bald.
Umbrella, hat and hood build a list of shelters and send you hunting for a fourth. The assumption to drop is that his head has hair on it; rain on a bald scalp wets no hair at all.
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32. What goes up as soon as the rain comes down? Easy
Most people first say: The water level
Show answer
An umbrella.
Goes up reads as rising the way floodwater rises, so rivers and puddles come to mind. The other sense is a thing you open and lift over your head the moment drops start to fall.
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33. You are locked in a room that contains only a bed, a calendar, and a piano. How do you eat, drink, and get out? Easy
Need a hint?
Each object hides a pun.
Show answer
Eat the dates from the calendar, drink from the springs of the bed, and use the keys of the piano to unlock the door.
Each object hides a second meaning: a calendar has dates, a bed has springs, and a piano has keys.
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34. Two friends play five games of checkers on the same afternoon. Each of them wins three games, and not one game ends in a draw. How? Medium
Most people first say: Somebody miscounted
Need a hint?
Nobody said they sat at the same board.
Show answer
They were not playing against each other. Each won three games against other people.
Two friends and five games invite the picture of one board between them. Nothing says they faced each other; each sat across from someone else, and three wins apiece adds up without any draw.
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35. You wind up an old fashioned alarm clock, set it for nine, and fall asleep at eight in the evening. How much sleep do you get before it rings? Medium
Most people first say: Thirteen hours
Need a hint?
The clock has no idea what AM means.
Show answer
One hour. A wind up clock cannot tell morning from evening, so it rings at nine that same night.
Eight to nine reads as evening to morning because that is when people sleep. A wind up clock has no idea which nine you meant and rings at the first one it reaches, sixty minutes later.
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36. How can a man go eight days without sleeping and feel fine? Medium
Show answer
He sleeps at night. The riddle only mentioned days.
You imagine eight sleepless 24-hour spans, but 'days' means daytime and he still sleeps each night.
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37. A pet shop promises that its parrot repeats every word it hears. A week later the buyer wants a refund because the bird has not spoken once, yet the shop told no lie. How? Medium
Most people first say: It was a stuffed toy
Need a hint?
The promise was about hearing, not speaking.
Show answer
The parrot is deaf. It repeats every word it hears, and it hears nothing.
Repeats every word it hears reads as a guarantee of talking, and the refund demand follows. The promise had a condition inside it, hearing, and a deaf bird meets the condition by never hearing a thing.
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38. Why are 2019 pennies worth more than 2018 pennies? Medium
Most people first say: Newer coins are worth more
Need a hint?
They are counts, not dates.
Show answer
Read them as amounts, not years. Two thousand nineteen pennies is one penny more than two thousand eighteen pennies.
Written as digits, 2019 and 2018 look like mint years, and the mind starts comparing collectible value. Read them as quantities of coins instead: the larger pile holds one extra cent.
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39. Two boys are born to the same mother on the same day, in the same month and year, yet they are not twins. How can that be? Medium
Most people first say: One was adopted
Show answer
They are two of a set of triplets.
Same mother, same day, same year sounds like the definition of twins, so the mind stops at two. The wording never limits the birth to two babies; a third sibling makes them part of a larger set.
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40. What question can you never honestly answer yes to? Medium
Show answer
Are you asleep yet? If you answer, the answer is no.
Honestly makes this sound like a riddle about lying, so you go looking for a paradox. What the question quietly requires is a person awake enough to reply, and anyone who can reply to are you asleep is not asleep.
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41. A woman shoots her husband, then holds him underwater for five minutes. A little later, the two of them enjoy a lovely dinner together. How? Medium
Most people first say: She used a water pistol
Show answer
She shot a photo of him and developed the film in a darkroom tray.
Shoots and holds underwater are read as violence, and the dinner afterward becomes the mystery. Both verbs belong to photography: you shoot a picture, then hold the film under liquid in a darkroom tray.
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42. A man jumps out of an airplane with no parachute and walks away without a scratch. How? Medium
Most people first say: He landed in water
Show answer
The plane was parked on the runway the whole time.
Airplane and no parachute plant the plane in the sky, though nothing in the sentence puts it there. Jumping out of a parked plane is a hop of a few feet, and no scratch is the natural result.
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43. A dog stands on one bank of a wide river and its owner calls from the other side. The dog crosses without a bridge or a boat and does not get wet. How? Medium
Most people first say: The dog jumped across
Need a hint?
Think about the season.
Show answer
The river is frozen. The dog trots straight across the ice.
Wide river, no bridge, no boat: the mind pictures water and starts inventing a leap. The season is the missing piece, since a river in deep winter is a solid floor a dog can trot over.
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44. What has a foot on each end and another foot in the middle? Medium
Show answer
A yardstick.
You picture a creature with real feet, but foot means the length unit: a three-foot yardstick has one at each end and one in the middle.
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45. What has a head and a tail, is brown, and has no legs? Medium
Most people first say: A snake
Show answer
A penny. Heads on one side, tails on the other.
Head, tail, brown, and no legs steer you toward an animal, but they describe the two sides of a penny.
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46. What is the very last thing you take off before you climb into bed? Medium
Most people first say: Your socks
Show answer
Your feet, off the floor.
You read take off as removing clothing, but the last thing you take off the floor is your feet as you climb in.
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47. A farmer keeps one haystack in the east field and two haystacks in the west field. If he combines them all, how many haystacks does he have? Medium
Most people first say: Three haystacks
Show answer
One. Pile them together and you get a single big haystack.
Adding one and two is set up so neatly that the sum answers itself. Combines is the word that undoes it: hay pushed into a single heap is a single heap, whatever the count was in the fields.
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48. Name three keys that cannot open any lock. Medium
Show answer
A monkey, a donkey, and a turkey.
Keys pulls the mind to locks, doors and pianos. The letters k, e and y are hiding at the tail of three animal names, and a creature that ends in key opens nothing.
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49. What has its bottom at the top? Medium
Show answer
Your legs. The bottom sits at the top of them.
Bottom reads as the base of an object, so you go looking for something built upside down. The word is also a polite name for the part you sit on, which is where a pair of legs ends.
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50. A hardware store sells 1 for one dollar, 12 for two dollars, and 144 for three dollars. What is it selling? Medium
Most people first say: Eggs by the dozen
Need a hint?
You buy them one digit at a time.
Show answer
House numbers. The price depends on how many digits you need.
Prices that climb by a dollar for 1, 12 and 144 look like a bulk deal gone wrong. Count the digits instead of the items: one, two and three, a dollar per digit, and the store sells numbers for front doors.
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51. A man in a small town married twenty different women. None of them died and he never divorced, yet he broke no law. How? Medium
Most people first say: A wedding in each country
Show answer
He is a minister. He performed the weddings, he was not the groom.
Married is read as took a wife, which makes twenty a scandal. The verb also means performed the ceremony, and a man who officiates weddings marries couples all year without becoming a husband once.
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52. You have two coins that add up to 30 cents, and one of them is not a nickel. What are the two coins? Medium
Most people first say: It cannot be done
Show answer
A quarter and a nickel. One of them, the quarter, is not a nickel. The other one is.
You take one is not a nickel to mean neither coin is a nickel, but only that one specific coin, the quarter, is not the nickel.
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53. If a red house is made of red bricks and a blue house is made of blue bricks, what is a greenhouse made of? Medium
Most people first say: Green bricks
Show answer
Glass. A greenhouse is for growing plants.
Two examples set a pattern, color plus bricks, and the pattern does the fooling. A greenhouse is not a house painted green; the word names a glass building for plants, so the pattern was never going to hold.
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54. What is the longest word in the dictionary? Medium
Most people first say: The word antidisestablishmentarianism
Show answer
Smiles. There is a whole mile between the first and last letter.
Longest sends you counting letters in medical and chemical terms. Take longest as a distance instead and look for a word with the letters m, i, l, e sitting between its first and last.
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55. A truck driver goes the wrong way down a one way street, passes five police officers, and none of them stops him. Why? Medium
Most people first say: The officers were off duty
Show answer
He is walking, not driving.
The words truck driver and one way street make you picture him at the wheel, but at that moment he is on foot walking.
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56. A waiter carries a tray of twelve drinks up three flights of stairs. On the top step he trips, and the whole tray flips upside down. Not one drop is spilled. How? Medium
Most people first say: The glasses were empty
Show answer
Every drink was still sealed in its bottle. Nothing had been opened yet.
Tray, drinks and a flip paint open glasses in the air. Nothing says a single one had been poured; drinks still capped in their bottles can turn a full somersault and lose nothing.
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57. Why can you never take a photo of a man with a wooden leg? Medium
Show answer
Because a wooden leg cannot take photos. You need a camera.
You read with a wooden leg as describing the man, but it names the tool, and you take photos with a camera, not a leg.
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58. A tall delivery truck gets wedged tight under a low bridge and the tow trucks cannot pull it free. A kid on a bike solves the problem in ten seconds. How? Medium
Most people first say: Cut the top off
Need a hint?
Do not raise the bridge. Lower the truck.
Show answer
Let some air out of the tires. The truck sinks a few inches and drives out.
Wedged tight makes everyone think about the bridge and the roof, the two things pressed together. The kid questions the height of the truck itself: air out of the tires lowers it, and lower is all it needed.
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59. What can you put between 7 and 8 to get a number bigger than 7 but smaller than 8? Medium
Most people first say: Insert a digit
Show answer
A decimal point. 7.5 sits right between them.
Between 7 and 8 sounds like a slot for another digit or an operator, and both make the value jump. A dot is neither; the decimal point turns two digits into one number, seven and a half.
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60. A rope ladder hangs over the side of a boat with its bottom rung touching the water. The tide rises one foot every hour. After three hours, how many rungs are underwater? Medium
Most people first say: Three rungs
Show answer
None. The boat rises with the tide, and the ladder rises with the boat.
A rising tide and one foot per hour set a count of rungs going, three hours, three rungs. The boat is not fixed to the seabed: it floats, the ladder hangs from it, and both lift with the water.
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61. How can a pocket be completely empty and still have something in it? Medium
Show answer
It can have a hole in it.
You read empty as nothing inside, but a hole counts as something in the pocket while it still holds no contents.
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62. What can you always find at the end of a rainbow? Hard
Most people first say: A pot of gold
Need a hint?
Spell it out and look at the very end.
Show answer
The letter W. Look at the end of the word rainbow.
End of a rainbow is a place in legend, so the mind goes to leprechauns and gold. Treat rainbow as a written word instead and its end is the final letter on the page.
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63. You see a boat filled with people, yet there is not a single person on board. How is that possible? Hard
Need a hint?
Think about relationship status, not head counts.
Show answer
Everyone on board is married. There is not a single person among them.
You read single person as one human, but single means unmarried, and everyone aboard is married.
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64. How do you spell cow in fourteen letters? Hard
Most people first say: It cannot be done
Need a hint?
Say the names of the letters, not the word.
Show answer
SEE O DOUBLE YOU.
Fourteen letters invites stuffing extra letters into a three letter word. Spell each letter by its name instead, the way you would over a phone, and three short names stretch the word into a long string.
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65. What begins with an E, ends with an E, and usually contains just one letter? Hard
Need a hint?
It travels through the mail.
Show answer
An envelope.
Contains one letter sounds like a rule about spelling, and a word that is nothing but E seems impossible. Letter also means a note you post, and the paper pocket that carries it starts and ends with E.
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66. A man pushes his car up to a hotel and instantly knows he is bankrupt. What happened? Hard
Most people first say: He crashed into the hotel
Need a hint?
The car fits in his hand.
Show answer
He is playing Monopoly and landed on a hotel he cannot afford.
Pushes his car reads as a breakdown, and a hotel bill that ruins a man sounds like a long stay. Car and hotel are both game pieces here: a tiny token moved onto a rival's property with rent he cannot cover.
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67. Which five-letter word keeps its exact pronunciation after you delete four of its letters? Hard
Most people first say: There is no such word
Need a hint?
It is a line of people waiting their turn.
Show answer
Queue. Drop the last four and it still sounds like Q.
Pronunciation and deletion seem locked together, so the demand looks impossible. One word is spoken as a single letter name; strip everything after that first letter and the mouth does the same thing.
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68. Forward I weigh a great deal, but backward I weigh nothing at all. What word am I? Hard
Need a hint?
A unit of weight, written in three letters.
Show answer
Ton. Spelled backward it becomes not.
Weigh a great deal points at heavy objects, an anvil or an elephant. Forward and backward are the clue that this is a word being reversed, and a unit of weight read right to left becomes a plain no.
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69. What five-letter word actually becomes shorter when you add two letters to it? Hard
Most people first say: No word can
Need a hint?
Add the two letters that make a comparison.
Show answer
Short. Add e and r to get shorter.
Adding letters makes any word longer on the page, so becomes shorter reads as a contradiction. Shorter is also just a word, and the five letter word it is built from is sitting inside the question.
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70. I am an odd number, but take a single letter away and I turn even. Which number am I? Hard
Need a hint?
Spell the number out and drop its first letter.
Show answer
Seven. Remove the s and you get even.
Odd and even pull you into arithmetic, but no subtraction turns an odd value even. Spell the number out and the puzzle is about letters: one consonant gone from the front leaves the word even.
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71. Before Mount Everest was ever discovered, which mountain was the tallest on Earth? Hard
Most people first say: Mount K2
Need a hint?
Discovery changes what we know, not what is there.
Show answer
Mount Everest. It was already the tallest, just not yet found.
Before it was discovered plants the idea that a title needs a record holder on a list. Height does not wait for a survey; the mountain stood at its full size before anyone climbed or named it.
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72. A man builds a house with all four walls facing due south. A bear wanders past. What color is the bear? Hard
Most people first say: A brown bear
Need a hint?
Where on Earth can every wall face south?
Show answer
White. The house sits on the North Pole, so it is a polar bear.
The only spot where every wall faces south is the North Pole, and the only bears there are white.
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73. The moment you share me I am gone, yet everyone is tempted to give me away. What am I? Hard
Need a hint?
You keep it by not telling it.
Show answer
A secret.
Share and give away sound like handing over an object, so you look for a possession that leaves your hands. Both verbs also mean tell, and a thing you keep by staying quiet stops existing the moment it is told.
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74. Two fathers and two sons go fishing. Each catches exactly one fish, yet only three fish come home. How? Hard
Most people first say: Someone caught nothing
Need a hint?
One person can hold two titles.
Show answer
There are only three people: a grandfather, his son, and his grandson.
Four fishermen is the number the reader supplies; the text only lists titles. One man in the middle generation is both a son to the eldest and a father to the youngest, so three people carry the four titles and three fish are plenty.
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75. A doctor hands you three pills and says take one every half hour. How long until the pills are gone? Hard
Most people first say: Ninety minutes
Need a hint?
The first one goes down right away.
Show answer
One hour. You take the first now, the second at thirty minutes, the third at sixty.
Three pills and a half hour gap invite three times thirty. The first pill is taken at once, and the gaps are what get counted: only two of them separate the three doses, sixty minutes in all.
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76. A butcher is six feet tall and wears size twelve shoes. What does he weigh? Hard
Most people first say: About two hundred pounds
Need a hint?
Think about what he does at work.
Show answer
Meat. Weighing it is his job.
Height and shoe size set up a body-stat question, so a number in pounds comes next. Weigh has an active sense too, to put things on a scale, and that is what a butcher does with his stock.
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77. Take 30, divide it by half, then add ten. What is the result? Hard
Most people first say: Twenty five
Need a hint?
By half and in half are not the same.
Show answer
Seventy. Dividing by half means dividing by one half, so 30 becomes 60, plus ten.
You read divide by half as cut in two and guess twenty-five, but dividing 30 by one half gives 60, and ten more is 70.
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78. Mr. Reed has four daughters, and each daughter has exactly one brother. How many children does he have in total? Hard
Most people first say: Eight children
Need a hint?
Count the boys, not the sisters.
Show answer
Five. The four girls all share the same single brother.
Four daughters and exactly one brother each invite a multiplication, four brothers for four girls. Each is the word to reread: the sisters can all be describing the same boy, and the family has one son.
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79. You are in a foot race and you manage to overtake the runner in last place. What position are you in now? Hard
Most people first say: Second to last
Need a hint?
Think about who is behind the last runner.
Show answer
It is impossible. To pass the last runner you would have to be behind them, so they were never last.
Overtake sets the same trap as the second place version, so people start shuffling positions again. Being behind the last runner is a contradiction: if anyone is behind them, they were never last to begin with.
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80. What word do even the sharpest professors always pronounce wrong? Hard
Need a hint?
The question already contains the answer.
Show answer
The word wrong.
Professors and pronounce make this sound like a quiz about a difficult name. The word points at itself: however carefully anyone says wrong, they have pronounced wrong, which is what the question demanded.
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81. Turn me on my side and I am endless. Slice me down the middle and I am nothing. What am I? Hard
Most people first say: An hourglass
Need a hint?
It is a numeral, not an object.
Show answer
The number eight. Sideways it becomes the infinity sign, and cut in half it makes zeros.
Endless and nothing read as riddle poetry about time or the sea. The clues are about the shape of a written figure: lay it on its side and it is the infinity sign, cut it across the middle and two zeros are left.
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82. Which everyday English word contains three sets of double letters in a row? Hard
Most people first say: The word committee
Need a hint?
Someone who keeps the accounts.
Show answer
Bookkeeper. It stacks oo, kk, and ee back to back.
Everyday sends you scanning short common words, where doubles come one at a time. The job title for someone who keeps the ledgers runs oo, kk, ee with nothing between, and it is in ordinary use.
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83. A man studies a portrait and says, brothers and sisters I have none, but this man's father is my father's son. Who is in the portrait? Hard
Most people first say: The man himself
Need a hint?
Work out who my father's son is, then keep going.
Show answer
His own son.
My father's son unravels to the speaker, and most people stop there and point at him. The riddle says that person is the father of the man in the frame, so the picture shows the next generation down.
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84. What appears once in every minute, twice in a moment, yet not once in a hundred years? Hard
Most people first say: A second
Need a hint?
Look at how the three words are spelled.
Show answer
The letter M.
Minute, moment and a hundred years are units of time, so the hunt begins among heartbeats and ticks. Look at the spelling instead: one written character shows up in the first word once, in the second twice, and never in the third.
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85. Which single word contains all twenty-six letters? Hard
Most people first say: A pangram sentence
Need a hint?
Contains does not have to mean spelled with.
Show answer
Alphabet. It is the word that names all of them.
Contains is heard as spelled with, and no English word carries every letter in its spelling. Contains also means holds or stands for, and one eight letter word is the name for the full set from A to Z.
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86. How much dirt is there in a hole two feet wide, two feet long, and two feet deep? Hard
Most people first say: Eight cubic feet
Need a hint?
Think about what digging leaves behind.
Show answer
None. A hole has no dirt in it, which is what makes it a hole.
Three measurements are laid out so the reader multiplies them and reports a volume. Dirt is the word that undoes the sum: digging removes the soil, and the space left behind holds none of it.
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87. What starts with a T, ends with a T, and is filled with T? Hard
Most people first say: A tent
Need a hint?
You pour it at four o'clock.
Show answer
A teapot.
Starts and ends with T reads as a spelling puzzle, so filled with T sounds like a word stuffed with that letter. The last T is the drink, heard aloud, and the object that holds it takes the first two.
Tricky riddles with answers for adults
A tricky riddle is a question whose wording plants a false assumption, so the answer that arrives first is the one the riddle was built to make you give. Unlike hard riddles, which demand layered reasoning, tricky ones are simple once you reread the sentence and spot the single word doing the damage. Asked how many animals of each kind Moses took onto the ark, most people say two before noticing that Noah built the ark, not Moses. Asked what position you are in after overtaking the runner in second place, most say first, though passing second place only puts you second. Five frogs sit on a log and one decides to jump, so five remain, because deciding is not jumping. The reliable method is to slow down, restate the question in your own words, and check which word you assumed instead of read.
Tricky questions that punish fast guesses
Break a promise without touching it. Watch your age go up and never come down. Slow readers win here.
Longer tricky riddles to tell out loud
A few of these are little stories, like the locked room with a bed, a calendar, and a piano. Great for parties.
Your score
FAQ about Tricky Riddles with Answers
What makes a riddle tricky instead of hard?
A tricky riddle contains one dropped assumption or one decoy number, and the answer is plain the moment you see it. A hard riddle stacks several second meanings or contradictions, so seeing through one only opens the next.
Why do smart people fall for tricky riddles?
Fluent readers fill in expected meaning at speed. Moses on the ark sounds right because the sentence has the rhythm of a Bible quiz, and the check that would catch the name never runs. Reading fast is the habit these riddles are built to punish.
How do you solve a tricky riddle without seeing the answer?
Reread the question and mark every fact you supplied yourself: that a person is alive, that a plane is flying, that two numbers need adding. Then answer what the sentence literally says instead of the scene you pictured.
Once you have caught yourself adding facts a few times, the habit sticks. Carry it into the hard riddles, where the assumptions come stacked three deep, or into the lateral thinking puzzles, which let you interrogate the scene one yes or no at a time.