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So you think you’re a pro at solving brainteasers, and no tricky riddles baffle you? Well then, we’re a bit jealous because that means your critical thinking abilities are among the likes of Sherlock Holmes and Hercule Poirot. However, if you’d like to really test your problem-solving prowess, we’ve made a list full of very tricky riddles – have a go at them!

But before you do, have you ever wondered what these hard riddles really are? Well, it turns out these brain busters are classified as verbal puzzles with double or veiled meanings. Moreover, everyone’s beloved fun riddles can be divided into two types: enigmas (yeah, like that ’90s band!), which are problems expressed in metaphorical or allegorical language, and conundra, which are questions relying on puns (either in the question or in the answer). Now, it’s up to you to decide which type of brainteaser you like better, but we think that enigmas do make really tricky riddles. And lastly, before we skip to our selection of short tricky riddles with answers, you might find it amusing to know that the oldest known riddles come from the Babylonian times! Turns out, we have loved tricking each other and picking our brains since the dawn of civilization (if not earlier, who knows!). 

Right, with all the introductions done, it’s probably the time to start solving! Our picks of the most awesome tricky riddles with answers are just a bit further down, and once you are there, be sure to give the riddles that stumped you your vote. After that, share this article with your friends and see how they do with these tricky riddles. 

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#1

A woman is sitting in her hotel room when someone knocks at the door. She opened the door to find a man she’s never seen before. He says, “Oh I’m sorry, I made a mistake and thought this was my room.” He then ran away and got into an elevator so the woman shut her door and phoned security. What made the woman so suspicious?

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Verified 1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Answer: You don’t knock on your own hotel room door.

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#2

120 Really Tricky Riddles To Test Your Wits Three different doctors said that Paul is their brother yet Paul claims he has no brothers. Who is lying?

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Verified 1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Answer: No one is lying because the three doctors are Paul’s sisters.

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#3

What comes once in a minute, twice in a moment, but never in a thousand years?

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#4

A murderer is condemned to death and he has the option to die in one of the following three rooms: a room full of raging fire, a room full of assassins with loaded guns, and a room full of lions who haven’t eaten in years. Which room should he choose?

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Verified 1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Answer: The room with the lions because if they haven’t eaten in years then they’re already dead.

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#5

120 Really Tricky Riddles To Test Your Wits What English word has three consecutive double letters?

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#6

What is full of holes but still holds a lot of water?

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#7

You measure my life in hours and I serve you by expiring. I’m quick when I’m thin and slow when I’m fat. The wind is my enemy.

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#8

What is seen in the middle of March and April that can’t be seen at the beginning or end of either month?

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#9

Which English word is the odd one out: Stun, Ton, Evil, Letter, Mood, Bad, Strap, Snap, and Straw?

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Verified 1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Answer: Letter as it is the only one that does not spell another word when it’s written backward.

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#10

120 Really Tricky Riddles To Test Your Wits What gets wet while drying?

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#11

Why is Europe like a frying pan?

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#12

How can you physically stand behind your father while he is standing behind you?

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Verified 1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Answer: You are standing back-to-back with your father.

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#13

What falls but never breaks? What breaks but never falls?

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#14

Two fathers and two sons come home from the mall. Yet when they arrive home, only three people get out of the car. How is this possible?

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#15

120 Really Tricky Riddles To Test Your Wits When I am needed by you, you throw me away, but when I’m of no use, you take me back. What am I?

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#16

Humans purchase me to eat but then never eat me. What am I?

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#17

What word starts with E and ends with E but only has one letter?

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#18

I fly without wings and cry without eyes. Wherever I lead, darkness follows. What could I be?

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#19

Where can you finish a book without finishing a sentence?

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#20

120 Really Tricky Riddles To Test Your Wits What’s unique about this number: 854, 917, 632?

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Verified 1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Answer: It’s the numbers 1 through 9 in alphabetical order.

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#21

First you throw away the outside and cook the inside and then you eat the outside and throw away the inside. What am I?

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#22

What has thirteen hearts but no other organs?

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#23

What is caught but never thrown?

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#24

A man is looking at a photo of a man on the wall and states, “Brothers and sisters I have none, but this man’s father is my father’s son.” How are the men related?

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#25

120 Really Tricky Riddles To Test Your Wits The more there is, the less you see. What am I?

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#26

What’s black when you get it, red when you use it, and white when you’re all through with it?

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#27

My rings are not of gold, but I get more as I get old. What am I?

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#28

What has a heart that doesn’t beat?

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#29

What tastes better than it smells?

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#30

A man is trapped in a room that contains only two exits. The first exit is constructed of magnifying glasses that fry anything that walks through when the sun is out and blazing hot. The second exit includes a fire-breathing dragon that is bound and determined to kill. How does the man escape?

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Verified 1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Answer: He waits until nighttime and then runs through the first exit.

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#31

120 Really Tricky Riddles To Test Your Wits It’s shorter than the rest, but when you’re happy, you raise it like it’s the best. What is it?

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#32

A man is driving along and sees three doors: a diamond, ruby, and emerald. Which does he open first?

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#33

What is 3/7 chicken, 2/3 cat, and 2/4 goat?

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#34

What can you hold in your right hand, but never in your left hand?

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#35

120 Really Tricky Riddles To Test Your Wits If an electric train is moving north at 55 mph and the winds blowing east at 70 mph, which way does the smoke blow?

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#36

If there are three cups of sugar and you take one away, how many do you have?

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#37

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

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#38

What can fill an entire room without taking up any space?

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#39

What has ten letters and starts with gas?

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#40

120 Really Tricky Riddles To Test Your Wits The more these are taken, the more they are left behind. What are they?

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#41

A man runs away from home, turns left three times, and ends up back at home facing a man in a mask. Who is wearing the mask?

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Eligijus Sinkunas
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Verified 1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Answer: The man in the mask is a catcher because this is a game of baseball.

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#42

We hurt without moving and poison without touching. We bear truth and lies but are no judged by size. What are we?

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#43

What can run but never walk, have a mouth but never talk, have a head that never weeps, and a bed that never sleeps?

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#44

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

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#45

120 Really Tricky Riddles To Test Your Wits You see a boat filled with people. It has not sunk, but when you look again you don’t see a single person on the boat. Why?

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#46

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?

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#47

What are the next three letters in this combination? OTTFFSS

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Verified 1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Answer: E N T (Each letter represents the first letter in the written numbers: One, Two, Three, Four, Five, etc.).

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#48

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?

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#49

There is a single-story blue house where everything is blue; the doors, windows, couch, television, kitchen, etc. are blue. What color is the carpet on the stairs in this house?

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#50

120 Really Tricky Riddles To Test Your Wits How is it possible to drop an egg onto a concrete floor without cracking it?

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Verified 1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Answer: Concrete floors won’t crack from an egg dropping on them.

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#51

My buddies and I were inseparable mates until one by one we were split. My teacher then gave me a smack on the head so off in the corner I sit. What am I?

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#52

What is it that no one wants but no one wants to lose?

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#53

You always find me in the past, I can be created in the present, but the future can never taint me. What am I?

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#54

What spends all the time on the floor but never gets dirty?

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#55

120 Really Tricky Riddles To Test Your Wits You are my brother, but I am not your brother. Who am I?

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#56

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

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#57

What has four wheels and flies?

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#58

What starts with T, ends with T, and has T in it?

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#59

Who has married many people but has never been married himself?

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#60

120 Really Tricky Riddles To Test Your Wits What do you call a nose that's 12 inches long?

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#61

What has hands but cannot clap?

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#62

What has many keys but cannot open a single lock?

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#63

What gets smaller every time it takes a bath?

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#64

I have cities, but no houses. I have mountains, but no trees. I have water, but no fish. What am I?

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#65

120 Really Tricky Riddles To Test Your Wits How many letters are in the alphabet?

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Eligijus Sinkunas
Eligijus Sinkunas
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Verified 1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Answer: There are 11 letters in the words “the alphabet”.

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#66

What is able to go up a chimney when down but unable to go down a chimney when up?

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#67

How can you throw a ball as hard as you can only to have it come back to you without it bouncing off of anything?

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#68

There are 6 sisters. Each sister has 1 brother. How many brothers are in the sister’s family?

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#69

A woman shoots her husband and then holds him underwater for five minutes. Next, she hangs him but right after, they enjoy a nice dinner together. How is this possible?

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Verified 1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Answer: She took a photo of her husband and then developed it in her darkroom before dinner.

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#70

120 Really Tricky Riddles To Test Your Wits What has roots that no one sees and looms much taller than trees? Up it goes but yet it never grows; what is it?

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#71

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

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#72

What jumps when walking and sits when standing?

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#73

I eat to live and drink to die. What could I be?

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#74

The answer is “yes” but the intent means “no”. What is the question?

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#75

John and Kelly are long-distance lovers and John has just purchased an engagement ring for Kelly. He wants to mail the ring to her but to make sure it isn’t stolen he wants to put a lock on the package. However, John has locks and Kelly has locks but neither has a key to each other’s locks. Without sending another letter/package, how can they get the ring to Kelly and ensure it isn’t stolen in the process?

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Melissa Milner
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1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

If they can’t figure this out, maybe they shouldn’t get married.

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#76

120 Really Tricky Riddles To Test Your Wits What type of dress can never be worn?

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#77

What always ends everything?

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#78

Which part of a boat does a shopaholic like the most?

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#79

A man drove from New York City to Los Angeles in four days. At the end of his trip, he discovered that one of his tires had been punctured. How was he able to make the drive?

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#80

120 Really Tricky Riddles To Test Your Wits What goes up but never comes down?

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#81

I speak without a mouth and hear without ears. I have no body, but I come alive with wind. What am I?

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#82

First you eat me, then you get eaten. What am I?

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#83

Steve was murdered on Saturday afternoon. His wife said she was reading. The doorman said he was in the shower. The chef said he was making breakfast. The gardener was pruning hedges. From the information given, who committed the murder?

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Eligijus Sinkunas
Eligijus Sinkunas
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Verified 1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Answer: The chef because Steve was murdered in the afternoon yet the chef’s alibi was that he was making breakfast.

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#84

My first is in chocolate but no in ham. My second is in cake and also in jam. My third at tea-time is easily found. Altogether, this is a friend who is often around. What is it?

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Verified 1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Answer: A cat; chocolate but not ham (letter “c”), in cake and jam (letter “a”), and tea-time is easily found (letter “t”).

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#85

120 Really Tricky Riddles To Test Your Wits Bennett pushed his car into a hotel and lost his fortune. How?

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#86

How do you eat an elephant?

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#87

Each day, many people from around the world visit me; however, they usually only stay for a few minutes. I am considered by many to be very dirty, yet few people would want to live without me. And whenever people come to see me, they show a part of themselves that they rarely show to others. What am I?

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#88

What ancient invention still used in parts of the world today enables people to see through walls?

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#89

Which is heavier: a ton of sand or a ton of feathers?

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No Name
No Name
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1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

The feathers because you also have to carry the weight of what you did to all those poor birds.

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#90

120 Really Tricky Riddles To Test Your Wits I come from a mine and get surrounded by wood always. Everyone uses me. What am I?

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#91

How is seven different from the rest of the numbers between one and ten?

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Eligijus Sinkunas
Eligijus Sinkunas
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Verified 1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Answer: Seven has two syllables and the other numbers only have one syllable.

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#92

I possess a halo of water, walls of stone, and a tongue of wood. Long I have stood; what am I?

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#93

A man is asked what his daughters look like. He answers, “they are all blondes, but two, all brunettes, but two, and all redheads, but two.” How many daughters does he have?

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Verified 1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Answer: Three. One is blonde, one is brunette, and one is a redhead.

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#94

What word of five letters has only one left when two are removed?

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#95

120 Really Tricky Riddles To Test Your Wits Mike and Pat are in a desert. They both have packs on. Pat is dead. Mike, who is alive, has his pack open. Pat has his pack closed. What is in the packs?

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#96

John walks into a bar and asks for a glass of water. The bartender then shoots the ceiling with a gun. John says thank you and walks out. Why did John want the water?

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Verified 1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Answer: He had hiccups. The bartender used the surprise method to shock him out of his hiccups.

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#97

Walk on the living; they don’t even mumble. Walk on the dead, they mutter and grumble. What are they?

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#98

Mr. Taylor has four daughters and each has a brother. In total, how many children does Mr. Taylor have?

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Eligijus Sinkunas
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Verified 1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Answer: Five children because all of his daughters have the same brother.

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#99

Two girls were born to the same mother, on the same day, at the same time, in the same month, and in the same year, however, they’re not twins. How is this possible?

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Verified 1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Answer: The two girls are a part of a set of triplets.

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#100

120 Really Tricky Riddles To Test Your Wits If you’re eight feet away from a door and each move advances you half the distance to the door, how many moves does it take to reach the door?

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Verified 1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Answer: The door will never be reached because each move will always only get you half the distance.

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#101

I have two coins that equal fifteen cents but one of them is not a nickel. What two coins are they?

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Verified 1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Answer: A dime and a nickel because one of them is not a nickel but the other one is.

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#102

A man is found hanging dead from his ceiling where the room’s dimensions measure 15 x 15 x 15. However, the man is only 6 feet tall and the rope was only 2 feet long. If there are no windows, the only door was bolted shut from the inside, and there is a puddle of water beneath him, how did he kill himself?

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Verified 1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Answer: The man stood on a block of ice and waited for it to melt to be hung.

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#103

If 9999 = 4, 8888 = 8, 1816 = 3, and 1212 = 0, then what does 1919 = ?

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Verified 1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Answer: 1919 = 2. The riddle is about the closed sections of a number. For example, the top of a nine is closed so 9999 has four closed parts. Similarly, the top and bottom of an eight are closed so 8888 has eight closed parts.

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#104

Which will burn longer: the candles on the birthday cake of a boy or the candles on the birthday cake of a girl?

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Verified 1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Answer: No candles burn longer – they all burn shorter.

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#105

120 Really Tricky Riddles To Test Your Wits A man goes out in heavy rain with nothing to protect him from it. His hair doesn’t get wet. How does he do that?

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#106

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

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#107

I have a single eye but can’t see. What am I?

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#108

I have keys, but no locks and space, and no rooms. You can enter, but you can’t go outside. What am I?

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#109

A man attending his mother’s funeral, sees a woman in another pew, and experiences love at first sight. He tries to find her but has no luck. A few weeks later, he kills his sister. Why does he kill his sister?

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Verified 1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Answer: He kills his sister in hopes of seeing the woman at her funeral.

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#110

120 Really Tricky Riddles To Test Your Wits When I am alive I do not speak. Anyone who wants to, takes me captive and cuts off my head. They bite my bare body. I do no harm to anyone unless they cut me first. Then I soon make them cry. What am I?

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#111

What is as big as an elephant but weighs nothing?

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#112

What has a head, and a tail, is brown, and has no legs?

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Ela
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1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

A... copperhead. Also other brown snakes. I mean penny, sure but why not snek?

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#113

A is the brother of B. B is the brother of C. C is the father of D. So how is D related to A?

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#114

I am a five-letter word and people eat me. If you remove the first letter I become an energy form. If you remove the first two letters, I am needed to live. Scramble the last three letters and I am a drink. What word am I?

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#115

120 Really Tricky Riddles To Test Your Wits A boy and an engineer were fishing. The boy is the son of the engineer but the engineer is the father of the boy. Then who is the engineer?

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#116

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

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#117

You’re stuck in a room with no windows, doors, or vents to use to climb out. In the room with you is a light, a mirror, and a log of wood. How do you get out?

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#118

What can you hold in your left hand but not your right?

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#119

What is brown and sticky?

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Lacia Lew
Lacia Lew
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1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

So. Many. Things. Like, honey, melted chocolate, chocolate ice cream, melted brown sugar, etc etc

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#120

120 Really Tricky Riddles To Test Your Wits How can the number four be half of five?

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Eligijus Sinkunas
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Verified 1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Answer: IV, the Roman numeral for four, which is “half” (two letters) of the word five.

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