27 of the Hardest Riddles Ever—Can You Solve Them? (2024)

Table of Contents
Ready to be riddled? 1. I speak without a mouth and hear without ears. I have no body, but I come alive with wind. What am I? 2. 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. 3. I have cities, but no houses. I have mountains, but no trees. I have water, but no fish. What am I? 4. What is seen in the middle of March and April that can’t be seen at the beginning or end of either month? 5. 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? 6. What word in the English language does the following: 7. What English word has three consecutive double letters? 8. A woman shoots her husband, then holds him underwater for five minutes. Next, she hangs him. Right after, they enjoy a lovely dinner. Explain. 9. I come from a mine and get surrounded by wood always. Everyone uses me. What am I? 10. 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? 11. What disappears as soon as you say its name? 12. How can the number four be half of five? 13. I have keys, but no locks and space, and no rooms. You can enter, but you can’t go outside. What am I? 14. What gets wet while drying? 15. How many letters are in the alphabet? 16. 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? 17. What are the next three letters in this combination? OTTFFSS 18. This belongs to you, but everyone else uses it. 19. 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? 20. How is seven different from the rest of the numbers between one and ten? 21. First you eat me, then you get eaten. What am I? 22. What comes once in a minute, twice in a moment, but never in a thousand years? 23. Which word in the dictionary is always spelled incorrectly? 24. What can you hold in your right hand, but never in your left hand? 25. How can you physically stand behind your father while he is standing behind you? rd.com, Getty Images 26. What is able to go up a chimney when down but unable to go down a chimney when up? rd.com, Getty Images 27. Three different doctors said that Paul is their brother yet Paul claims he has no brothers. Who is lying?

RD.COM Humor Riddles

27 of the Hardest Riddles Ever—Can You Solve Them? (1)

ByMolly Pennington, PhD

Updated: Jul. 01, 2024

    Who doesn't love brain teasers and challenging riddles? If you think you’re already a pro at solving tricky riddles, put yourself to the test with these and find out! (Don't worry, answers are included.)

    27 of the Hardest Riddles Ever—Can You Solve Them? (2)

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    Ready to be riddled?

    Riddles are language brain teasers that use lateral thinking in order to come to a conclusion. They run the gamut from simple and easy to solve to serious brain-busters—and we’ve compiled several of the latter for your riddling enjoyment. The major head-scratchers in this list might take some big-time brain power to solve—but it sure feels great when you figure one out!

    (After you’re done here, you must find out if you can pass the world’s shortest IQ test that has stumped students at Yale and Harvard.)

    GetReader’s Digest‘sRead Up newsletterfor more riddles, games, humor, cleaning, travel and fun facts all week long.

    27 of the Hardest Riddles Ever—Can You Solve Them? (3)

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

    This riddle relies on tricking you into thinking about ears and a mouth. You get a tiny hint about wind to encourage you to think broadly and avoid the literal.

    Answer: An echo.

    27 of the Hardest Riddles Ever—Can You Solve Them? (4)

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    2. 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.

    This one wants to trip you up by hitting you with details from every angle. The big hint comes at the end with the wind. What does wind threaten most? You have to stretch your brain to come up with something tiny and unexpected.

    Answer: A candle.

    RELATED:Math Riddle Only the Smartest Can Get Right

    27 of the Hardest Riddles Ever—Can You Solve Them? (5)

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

    This riddle aims to confuse you and get you to focus on the things that are missing: the houses, trees, and fish. You might guess you need to think about something inanimate.

    Answer: A map.

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

    This riddle works by trying to get you to think about theweather or holidays or other events linked to a calendar. To get this one right you actually need to get super literal.

    Answer: The letter “R.”

    RELATED: Can you solve this viral riddle about Teresa’s daughter?

    27 of the Hardest Riddles Ever—Can You Solve Them? (7)

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    5. 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?

    Hard riddles like this are tricky because they seem to invite straightforward, logical thinking. You may come up with answers like “they all went below deck” or “jumped overboard.” But you need to focus on the word “single” and think about its other meanings.

    Answer: All the people were married.

    RELATED: Long Riddles to Give Your Brain a Workout

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    6. 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?

    This is hard because it gets you thinking about gender and the ways they’re different. You have to think of one word that holds the others. It’s easy when you think about it!

    Answer: Heroine.

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    7. What English word has three consecutive double letters?

    This one is pretty impossible but use the facts you know about English to get on track. First, think of words with double vowels. And you must know this is probably going to be a compound word. The first and last letters of those combined words will form one set of double letters. Now, just wrack your brain!

    Answer: Bookkeeper.

    RELATED: Let’s see how long it takes you to solve this “if I had four eggs” riddle.

    27 of the Hardest Riddles Ever—Can You Solve Them? (10)

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    8. A woman shoots her husband, then holds him underwater for five minutes. Next, she hangs him. Right after, they enjoy a lovely dinner. Explain.

    This puzzle aims to throw you off balance with shock. But pay attention to the first verb, “shoots.” What else can you shoot with besides a gun? There lies the key to the whole thing.

    Answer: She took a picture of him and developed it in her darkroom.

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    9. I come from a mine and get surrounded by wood always. Everyone uses me. What am I?

    The idea of a mine might lead you to coal or a diamond. The wood detail is your best hint. This riddle is a toughie, but wood might lead you to figure it out.

    Answer: Pencil lead.

    RELATED:Short Riddles That Will Still Stump You

    27 of the Hardest Riddles Ever—Can You Solve Them? (12)

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    10. 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?

    This trick question gives you a bunch of ways to get totally confused if you try to figure out the answer. The key is to keep it simple. Be sure to count the sisters and brothers in total and in terms of their own number of siblings. Then the answer gets a little easier.

    Answer: Four sisters and three brothers.

    RELATED: Toughest Tongue Twisters in the English Language

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    11. What disappears as soon as you say its name?

    Hard riddles like this one require you to think logically or in a straightforward way. At the same time, it’s employing a conceptual metaphor with the notion of something disappearing. The answer seems so simple—but not until you’ve figured it out! Before that moment, it’s got your brain in a twist.

    Answer: Silence.

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    12. How can the number four be half of five?

    You might start doing some elaborate fractions but hard riddles like this are sometimes much more about wordplay than crunching the numbers. Think literally and the answer may just appear right before your eyes.

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

    RELATED:Riddles for Teens

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

    This one tricks you by having you think about space that can be entered. Then it gets you to merge that with a space without rooms where you can’t leave. You might even be hung up on those keys. That’s where you should linger. Think about that word. What are some other meanings of “keys”—especially those that don’t require locks?

    Answer: A keyboard.

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    14. What gets wet while drying?

    This one has a simple answer even though it stumps most people who try to figure it out. Wet and dry seem like they always have to be opposite, so you might get tripped up. Think of an object that can, ahem (hint!) absorb or be both.

    Answer: A towel.

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    15. How many letters are in the alphabet?

    Some hard riddles trip you up by sending you to the easiest answer first. You got this one easy, right? Twenty-six—if you’re talking English alphabet. Not so fast. Take another look and get super simple and straightforward.

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

    RELATED:Christmas Riddles

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    16. 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?

    Riddles try to send your train of thought off in scattered directions. Try to stay clear and just follow the logic. Using letters as placeholders for names like “Uncle Bob” or “Aunt Linda” makes straightforward relationships seem difficult.

    Answer: A is D’s uncle.

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    17. What are the next three letters in this combination? OTTFFSS

    This super hard question asks you to determine the relationship between the letters. They seem random: a vowel, two consonants from the tail of the alphabet, two from the front, then two more. What could they mean? What’s the pattern? In this case, think of common strings of words to get you closer. But it still seems almost impossible to hit on the solution.

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

    27 of the Hardest Riddles Ever—Can You Solve Them? (20)

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    18. This belongs to you, but everyone else uses it.

    The key to this riddle is to think of anything else but an actual object. Use your critical thinking skills to get conceptual on this one.

    Answer: Your name.

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    19. 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?

    This riddle works by getting your brain to go through a series of associations so you get locked in and can’t think of alternatives. Be careful! Is the question really connected to that color you were asked to think about? Most folks say that cows drink milk because they’re fixated on the color white.

    Answer: Water.

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

    The math nerds may start thinking about prime numbers or whether seven is divisible by this or that or if it can be cubed and all that. Avoid thinking about math altogether and think about the literal quality of the words that signify the numbers. Remember that riddles play with the differences between the literal and the conceptual, or the straightforward and the complex. For this riddle, think simple, but pivot to a paradigm separate from numbers.

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

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

    Hard riddles get you used to thinking about metaphors and concepts. Not this one; keep it simple and literal to get to the solution. But ask yourself who or what the “you” is.

    Answer: A fishhook.

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

    Again, riddles like this often have you crunching the numbers and stretching your brain cells thinking all about time and the way it works. By now, you might’ve figured out that number riddles rarely involve math.

    Answer: The letter “M.”

    Want to conquer some more verbal trickery? Try solving the viral ‘how many numbers are on a clock’riddle.

    27 of the Hardest Riddles Ever—Can You Solve Them? (25)

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    23. Which word in the dictionary is always spelled incorrectly?

    Hard riddles obsess over wordplay and word games. This one has such an easy answer that it trips you up by getting you to think in a complex way. Some riddles require that. Not this one.

    Answer: “Incorrectly.”

    RELATED:Only 2 Percent of People Can Solve Einstein’s Riddle—Can You?

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

    Take it slow and easy with this one. Perhaps if take a look at your own hands, that might give you a clue based on logic.

    Answer: Your left hand.

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

    For this kind of super tricky riddle, you might do best to actually map out the physical relationship in your head—if you can! This riddle works by tricking you into thinking about impossibilities.

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

    Also, check out this viralPenny Has 5 Children Riddle.

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

    Try to think out of the box for this one. It may not be something you would normally find in your chimney.

    Answer:An umbrella.

    27 of the Hardest Riddles Ever—Can You Solve Them? (29)
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    27. Three different doctors said that Paul is their brother yet Paul claims he has no brothers. Who is lying?

    Visualize your family tree. That may help with this one.

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

    If you enjoyed being stumped by these riddles, test your smarts with these popular riddles you’ll want to share with everyone you know.

    Originally Published: July 16, 2021

    Author

    Molly Pennington, PhD

    Molly is a writer and collage artist with a PhD in film and cultural studies from the University of Pittsburgh. Her professional astrology services and artwork are available at Baroque Moon Astrology. She covers the zodiac, books, movies, TV and culture for Reader’s Digest, and loves to talk about all the ways we make meaning.

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