115 Tricky Short Riddles for Kids & Adults

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Plus, the riddle that stumped 98% of Harvard students
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Looking to exercise your brain with some tricky riddles? Then, look no further! Tricky or difficult riddles are a great way to keep your brain sharp and help you develop better reasoning skills. [1] Plus, they’re just plain fun. This collection includes over 105 tricky riddles across a variety of categories. Challenge yourself or stump your friends and family with these clever brainteasers!

Section 1 of 12:

Tricky Riddles for Kids

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  1. 1
    I speak without a mouth and hear without ears. I have no body, but I come alive with the wind. What am I?
    • Hint: The answer is a sound of some type.
    • Answer: An echo
  2. 2
    What has to be broken before you can use it?
    • Hint: Think about food items you have to crack open.
    • Answer: An egg
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  3. 3
    I'm tall when I'm young, and I'm short when I'm old. What am I?
    • Hint: I provide light and am often used in birthday celebrations.
    • Answer: A candle
  4. 4
    What goes up but never comes down?
    • Hint: It's a number that increases as time passes.
    • Answer: Your age
  5. 5
    The more of this there is, the less you see. What is it?
    • Hint: Think about what makes it harder to see.
    • Answer: Darkness
  6. 6
    How far can a dog run into the woods?
    • Hint: Think about what happens after you get to the middle of the woods.
    • Answer: Only halfway. After that, he's running out of the woods again.
  7. 7
    What is bought by the yard and worn by the foot?
    • Hint: Think about other meanings for the words “worn” and “foot.”
    • Answer: Carpet
  8. 8
    What has a mouth but can't talk?
    • Hint: Think about other types of mouths.
    • Answer: A river
  9. 9
    What has a foot but no leg?
    • Hint: Think about other meanings of the word “foot.”
    • Answer: Ruler
  10. 10
    What can you hold in your left hand and not in your right?
    • Hint: It’s a body part.
    • Answer: Your right elbow (or right wrist)
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Section 2 of 12:

Difficult Riddles for Adults

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  1. 1
    I have cities but no houses. I have mountains but no trees. I have water but no fish. What am I?
    • Hint: I represent a place but am not the actual place.
    • Answer: A map
  2. 2
    What belongs to you but gets used by everyone else more than you?
    • Hint: People use this to refer to you.
    • Answer: Your name
  3. 3
    I am not alive, but I grow; I don't have lungs, but I need air; I don't have a mouth, but water kills me. What am I?
    • Hint: I provide warmth and light.
    • Answer: Fire
  4. 4
    What can fill a room but takes up no space?
    • Hint: There are a couple of things that fit this riddle, and they both technically have weight but weigh very little.
    • Answer: Light (or air)
  5. 5
    A man dies of old age on his 25th birthday. How is this possible?
    • Hint: Consider a special day that only occurs every four years.
    • Answer: He was born on February 29th, a leap year. He only had a birthday every 4 years.
  6. 6
    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.
    • Hint: There are a lot of details, but the wind is the most important one.
    • Answer: A lit candle
  7. 7
    What is seen in the middle of March and April that can’t be seen at the beginning or end of either month?
    • Hint: Read this one literally.
    • Answer: The letter “R”
  8. 8
    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?
    • Hint: Focus on a word that holds all the others.
    • Answer: Heroine
  9. 9
    This belongs to you, but everyone else uses it.
    • Hint: It’s not a physical object.
    • Answer: Your name
  10. 10
    What are the next three letters in this combination? OTTFFSS
    • Hint: Think about the common words that you string together.
    • Answer: E N T (Each letter represents the first letter in the written numbers: One, Two, Three, Four, Five, etc.)
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Section 3 of 12:

Fun Tricky Riddles

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  1. 1
    What has four wheels and flies?
    • Hint: It's a vehicle that carries something smelly.
    • Answer: A garbage truck
  2. 2
    Why can't a bike stand on its own?
    • Hint: The answer is a play on words related to being exhausted.
    • Answer: It's two tired.
  3. 3
    What do you call a bear with no teeth?
    • Hint: Think of a sweet, chewy candy.
    • Answer: A gummy bear!
  4. 4
    What do you call a fish with no eyes?
    • Hint: Say the word "fish" out loud and remove the "i" sound.
    • Answer: A fsh.
  5. 5
    Why don't scientists trust atoms?
    • Hint: It's a joke about atoms being the building blocks of matter.
    • Answer: Because they make up everything!
  6. 6
    A man who was outside in the rain without an umbrella or hat didn’t get a single hair on his head wet. Why?
    • Hint: What are the reasons a man wouldn’t have wet hair?
    • Answer: He was bald.
  7. 7
    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?
    • Hint: Think about the number of babies born at the same time.
    • Answer: The girls are two out of three triplets.
  8. 8
    A man looks 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?
    • Hint: Think very carefully about the relationships the man says he has.
    • Answer: The man in the picture is his son.
  9. 9
    What is caught but never thrown?
    • Hint: It’s not an object.
    • Answer: A cold
  10. 10
    When I am needed by you, you throw me away, but when I’m of no use, you take me back. What am I?
    • Hint: Think about how the item is used.
    • Answer: An anchor
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Section 4 of 12:

Clever Riddles

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  1. 1
    What disappears as soon as you say its name?
    • Hint: This one is more straightforward than it seems. Think about things that disappear when you speak.
    • Answer: Silence
  2. 2
    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?
    • Hint: Give each letter a name and title, like Uncle Gary or Aunt Chris.
    • Answer: A is D’s uncle
  3. 3
    How can you physically stand behind your father while he is standing behind you?
    • Hint: Think through what it looks like to stand behind a person who is standing behind you.
    • Answer: You’re standing back-to-back with your father.
  4. 4
    Three different doctors said that Paul is their brother, yet Paul claims he has no brothers. Who is lying?
    • Hint: Be careful not to make assumptions about the doctors.
    • Answer: No one is lying. The doctors are Paul’s sisters.
  5. 5
    Penny has five children. The name of Penny’s first child is January. The second is called February. Penny’s third child answers to the name March. The fourth one’s name is April. What is the name of Penny’s fifth child.
    • Hint: The riddle literally tells you the answer.
    • Answer: The name of Penny’s fifth child is “What.”
  6. 6
    If an electric train is moving north at 55 mph and the winds are blowing east at 70 mph, which way does the smoke blow?
    • Hint: Think about types of trains and how they work.
    • Answer: An electric train doesn’t emit smoke.
  7. 7
    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?
    • Hint: Think about all the directions you can throw a ball.
    • Answer: You throw it straight up in the air.
  8. 8
    I am the beginning of the end of time and space that surrounds everything and every place. What am I?
    • Hint: This seems big and cosmic, but read it literally.
    • Answer: The letter “E”
  9. 9
    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?
    • Hint: Think about each person’s relationship to the others.
    • Answer: They are a grandfather, father, and son.
  10. 10
    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?
    • Hint: Read each sentence very carefully.
    • Answer: The room with the lions because if they haven’t eaten in years, then they’re already dead.
  11. 11
    Can you name three consecutive days without using the words Wednesday, Friday, or Sunday?
    • Hint: These are days, but they could be any day of the week.
    • Answer: Yesterday, today, and tomorrow
  12. 12
    Yesterday is always before today. But there is a place where yesterday always follows today. Where?
    • Hint: Think about a situation where today comes first.
    • Answer: The dictionary
  13. 13
    Who can finish a book without finishing a sentence?
    • Hint: Think about different types of sentences.
    • Answer: A prisoner
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Section 5 of 12:

Tricky Spelling Riddles

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  1. 1
    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?
    • Hint: Focus on a word that holds all the others.
    • Answer: Heroine
  2. 2
    What English word has three consecutive double letters?
    • Hint: Think of words with double vowels that you can put together. The last letter of one is going to be the first letter of the second one.
    • Answer: Bookkeeper
  3. 3
    What word begins with “e” and ends with “e” but only has one letter?
    • Hint: Think about the different meanings of the word “letter.”
    • Answer: Envelope
  4. 4
    What comes once in a minute, twice in a moment, but never in a thousand years?
    • Hint: Think about the words.
    • Answer: The letter “M”
  5. 5
    Which word in the dictionary is always spelled incorrectly?
    • Hint: Read it literally.
    • Answer: “Incorrectly”
  6. 6
    Which word, when written in all capital letters, looks the same when viewed upside down?
    • Hint: Think about letters that look like other letters or are the same when you flip them.
    • Answer: SWIMS
  7. 7
    What five-letter word becomes shorter when you add two letters to it?
    • Hint: This one is more literal than it seems.
    • Answer: Short
  8. 8
    If you throw me out the window, you’ll leave a grieving wife but drop me in the middle of a door, and you might just save a life. What am I?
    • Hint: This one is so tricky. Think about letters.
    • Answer: The letter “N”
  9. 9
    I am a word that begins with the letter “i.” If you add the letter “a” to me, I will become a new word with a different meaning that sounds exactly the same. What word am I?
    • Hint: Think about words that sound the same but have different meanings.
    • Answer: Isle (adding an “A” makes aisle.)
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Section 6 of 12:

Difficult Math Riddles

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  1. 1
    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?
    • Hint: Count the sisters and brothers in total and in terms of their own number of siblings.
    • Answer: Four sisters and three brothers.
  2. 2
    How can the number four be half of five?
    • Hint: Think about different types of numbers.
    • Answer: IV, the Roman numeral for four, which is “half” (two letters) of the word “five.”
  3. 3
    How is seven different from the rest of the numbers between one and ten?
    • Hint: Remember, sometimes math riddles are actually about words.
    • Answer: Seven has two syllables, and the other numbers only have one syllable.
  4. 4
    If two’s company and three’s a crowd, what are four and five?
    • Hint: This one is so tricky because it’s actually very simple.
    • Answer: Nine
  5. 5
    I am a three-digit number. My tens digit is five more than my ones digit. My hundreds digit is eight less than my tens digit. What number am I?
    • Hint: Just take a breath and work through numbers 1-9.
    • Answer: 194
  6. 6
    When you multiply me by any other number, the answer will always remain the same. What number am I?
    • Hint: This one is so easy it’s hard.
    • Answer: Zero
  7. 7
    I am an odd number. Take away one letter, and I become even. What number am I?
    • Hint: Take this riddle literally, and look carefully at the words.
    • Answer: Seven
  8. 8
    How many times can you subtract 10 from 100?
    • Hint: It’s not the first answer that comes to mind.
    • Answer: Once. After the first subtraction, you’re subtracting from 90.
  9. 9
    A man gave one son 10 cents, and another son was given 15 cents. What time is it?
    • Hint: This one is SUPER tricky. The answer is there, but you have to think about how what the man’s actions sound like when you put it all together.
    • Answer: 1:45. The man gave away a total of 25 cents (a quarter) to 2 people. "A quarter to 2:00" is another way of saying 1:45.
  10. 10
    I add 5 to 9 and get 2. The answer is correct, but how?
    • Hint: Think about time.
    • Answer: 2p.m. When it’s 9 a.m., adding 5 hours makes it 2 p.m.
  11. 11
    How do eight eights add up to one thousand?
    • Hint: You actually have to do some math to solve this one.
    • Answer: 888 + 88 + 8 + 8 + 8 = 1000
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Section 7 of 12:

Hard Riddles about Places

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  1. 1
    There is a one-story house in which everything is yellow. Yellow walls, yellow doors, yellow furniture. What color are the stairs?
    • Hint: Read the riddle again.
    • Answer: There aren’t any stairs in a one-story house.
  2. 2
    I possess a halo of water, walls of stone, and a tongue of wood. Long I have stood; what am I?
    • Hint: Try to picture walls of stone with a halo of water.
    • Answer: A castle
  3. 3
    If a plane came crashing down on the border between Canada and America, where are the survivors buried?
    • Hint: Read the question very carefully.
    • Answer: You don’t bury survivors.
  4. 4
    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?
    • Hint: The man in the mask isn’t trying to rob you, just get you out.
    • Answer: The man in the mask is a catcher at a baseball game.
  5. 5
    You walk into a room that contains a match, a kerosene lamp, a candle, and a fireplace. What would you light first?
    • Hint: Logically on of these has to come first.
    • Answer: The match
  6. 6
    I have branches but no fruit, trunk, or leaves. What am I?
    • Hint: This isn’t a plant. Think of other things that have branches.
    • Answer: A bank
  7. 7
    What runs all around a backyard but never moves?
    • Hint: Think about the different ways things run.
    • Answer: A fence
  8. 8
    You’ll find me in Mercury, Earth, Mars, and Jupiter, but not in Venus or Neptune. What am I?
    • Hint: Take this riddle very literally.
    • Answer: The letter “R”
  9. 9
    If you drop a yellow hat in the Red Sea, what does it become?
    • Hint: Color has nothing to do with it.
    • Answer: Wet
  10. 10
    An elephant in Africa is called Lala. An elephant in Asia is called Lulu. What do you call an elephant in Antarctica?
    • Hint: Think about where elephants usually go.
    • Answer: Lost
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Section 8 of 12:

Tricky Riddles about Nature

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  1. 1
    What can run but never walk, have a mouth but never talk, have a head that never weeps, and a bed that never sleeps?
    • Hint: Think about other meanings for “run,” “mouth,” “head,” and “bed” that don’t have anything to do with a person or animal.
    • Answer: A river
  2. 2
    What has roots that no one sees and looms much taller than trees? Up it goes, but it never grows; what is it?
    • Hint: Think about things that have roots but are not living.
  3. 3
    I fly without wings and cry without eyes. Wherever I lead, darkness follows. What could I be?
    • Hint: This isn’t an animal.
    • Answer: A cloud
  4. 4
    A woman is sitting in her hotel room when someone knocks at the door. She opened the door to find a man she’d 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?
    • Hint: Think very carefully about what the man says.
    • Answer: You don’t knock on your own hotel room door.
  5. 5
    What would you find in the middle of Toronto?
    • Hint: Think about what is literally in the middle of Toronto.
    • Answer: The letter “O”
  6. 6
    I’m light as a feather, yet the strongest person can’t hold me for five minutes. What am I?
    • Hint: This is not a thing you can carry in your hands.
    • Answer: Breath
  7. 7
    What’s at the end of the rainbow?
    • Hint: This is another literal question.
    • Answer: The letter “w”
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Section 9 of 12:

Tough Riddles with Wordplay

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  1. 1
    What has only two words but thousands of letters?
    • Hint: Think about different types of letters.
    • Answer: The post office
  2. 2
    What word has 10 letters and starts with gas?
    • Hint: The word “gas” isn’t at the beginning of the answer.
    • Answer:
  3. 3
    Forward I am heavy, but backward I am not. What am I?
    • Hint: Look at the actual words.
    • Answer: The word “not” is heavy because backward, it’s “ton.”
  4. 4
    What kind of coat is best put on wet?
    • Hint: Think about different types of coats.
    • Answer: A coat of paint
  5. 5
    What building has the most stories?
    • Hint: Think about different types of stories.
    • Answer: A library
  6. 6
    What is the difference between a jeweler and a jailer?
    • Hint: Think about what each one does for a living.
    • Answer: A jeweler sells watches and a jailer watches cells.
  7. 7
    I have keys, but no locks and space, and no rooms. You can enter, but you can’t go outside. What am I?
    • Hint: Think about different types of keys first.
    • Answer: A computer keyboard
  8. 8
    What gets wet while drying?
    • Hint: Think about words that could be different types of actions.
    • Answer: A towel
  9. 9
    I can shave every day, but my beard never changes. What am I?
    • Hint: Think about the person doing the shaving.
    • Answer: A barber
  10. 10
    They can be harbored, but few hold water. You can nurse them, but only by holding them against someone else. You can carry them, but not with your arms. You can bury them, but not in the earth.
    • Hint: There are several common turns of phrase that contain the answer.
    • Answer: Grudges
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Section 10 of 12:

Tricky Riddles about Plants & Animals

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  1. 1
    First, you eat me, then you get eaten. What am I?
    • Hint: “You” are a fish.
    • Answer: A fishhook
  2. 2
    I can sizzle like bacon, I am made with an egg, I have plenty of backbone but lack a good leg, I peel layers like onions but still remain whole, I can be long, like a flagpole, yet fit in a hole. What am I?
    • Hint: Think about animals that have a long backbone.
    • Answer: A snake
  3. 3
    A pet shop owner had a parrot with a sign on its cage that said, "This parrot repeats everything it hears." Jonathan bought the parrot, and for two weeks he spoke to it. It didn't say a word—so he complained to the shop owner, who said he didn’t lie. How is this possible?
    • Hint: Think about why a parrot might not be able to repeat something he heard.
    • Answer: The parrot is deaf, so he can’t hear anything.
  4. 4
    First, you throw away the outside and cook the inside, and then you eat the outside and throw away the inside. What am I?
    • Hint: Think about plants you eat.
    • Answer: Corn on the cob
  5. 5
    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, you need me to live. Scramble the last three letters, and I am a drink. What word am I?
    • Hint: Figuring out the word for what you need to live is the easiest part.
    • Answer: Wheat (heat, eat, tea)
  6. 6
    I’m red and small, and I have a heart of stone. What am I?
    • Hint: Think about stones that grow in the middle of things.
    • Answer: A cherry
  7. 7
    What has a head but no eyes, nose, or mouth?
    • Hint: It’s not an animal.
    • Answer: Lettuce
  8. 8
    What kind of room has no doors or windows?
    • Hint: Hopefully, this kind of room isn’t in your house.
    • Answer: A mushroom
  9. 9
    A rooster is sitting on the roof of a barn facing west. If it laid an egg, would the egg roll to the north or the south?
    • Hint: Really think about what types of animals lay eggs.
    • Answer: Roosters don’t lay eggs.
  10. 10
    What kind of lion never roars?
    • Hint: It’s not an animal.
    • Answer: A dandelion
  11. 11
    What grows up while growing down?
    • Hint: Think about other meanings of the word “down.”
    • Answer: A goose or duck
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Section 11 of 12:

Riddles about Life & Philosophy

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  1. 1
    What is it that no one wants but no one wants to lose?
    • Hint: If you have one, it’s a pain, but losing one is much worse.
    • Answer: A lawsuit
  2. 2
    The answer is “yes,” but the intent means “no.” What is the question?
    • Hint: Think about questions you ask when “yes” means you don’t want the person asking to do something.
    • Answer: “Do you mind?”
  3. 3
    We hurt without moving and poison without touching. We bear truth and lies but are not judged by size. What are we?
    • Hint: The answer is not a tangible thing.
    • Answer: Words
  4. 4
    What question can you never answer yes to?
    • Hint: What are the reasons you wouldn’t be able to answer yes to something?
    • Answer: Are you asleep yet?
  5. 5
    What is the end of everything?
    • Hint: Read it literally.
    • Answer: The letter “G”
  6. 6
    What did the triangle say to the circle?
    • Hint: Think about how triangles and circles are different.
    • Answer: “You are pointless.”
  7. 7
    What gets sharper the more you use it?
    • Hint: Think about different meanings of the word “sharp.”
    • Answer: Your brain
  8. 8
    If your uncle’s sister is not your aunt, what relation is she to you?
    • Hint: Think about who your uncle’s sisters are.
    • Answer: Your mother
  9. 9
    Until I am measured, I am not known. Yet how you miss me when I have flown. What am I?
    • Hint: Think about something that doesn’t really exist until you measure it.
    • Answer: Time
  10. 10
    What kind of ship has two mates but no captain?
    • Hint: Think about words that contain the word “ship.”
    • Answer: A relationship
  11. 11
    You can ask this question all day long and get completely different answers, yet all the answers will be correct. What is the question?
    • Hint: Think about a question that has different answers as time passes.
    • Answer: “What time is it?”
  12. 12
    What is always in front of you but can’t be seen?
    • Hint: Think about something people are always worried about that lies ahead.
    • Answer: The future
  13. 13
    What is one thing that all wise men, regardless of their politics or religion, have to agree is between heaven and Earth?
    • Hint: Think about what literally comes between heaven and earth.
    • Answer: The word “and”
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Section 12 of 12:

The Harvard Riddle

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  1. I turn polar bears white, and I will make you cry. I make guys have to pee, and girls comb their hair. I make celebrities look stupid and normal people look like celebrities. I turn pancakes brown and make your champagne bubble. If you squeeze me, I’ll pop. If you look at me, you’ll pop. Can you guess the riddle? [2]
    • This riddle is often called the "Harvard riddle" because it gained widespread attention after 98% of students at the prestigious university failed to solve it. While it's subjective to label any single riddle as the most difficult in the world, this particular conundrum is sometimes called “the world’s hardest riddle.”
    • Answer : “No.” Most of the riddle is meaningless. The only line that matters is the last one: “Can you guess the riddle?” The answer is “No” because nothing fits the rest of the description.

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      References

      1. ↑ https://www.psychologytoday.com/us/blog/brain-workout/200904/puzzles-and-the-brain
      2. ↑ https://parade.com/living/worlds-hardest-riddle

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