25 of the Toughest Riddles Ever. Can You Solve Them?

Riddle me this, Batman! Why are these brain-twisting riddles so hard? See if you can find the answers!

Say what?

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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.

The Answer: an Echo

(Feeling smart? Here are 33 middle school vocab words adults still get wrong.)


Match game

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Riddles want to trip you up, and this one works 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 a something tiny and unexpected.

The Answer: a Candle

(Can you figure out this viral riddle that has the Internet scratching its head?)

Hidden treasure

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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.

The Answer: a Map

(Only two percent of people can solve Einstein's riddle—can you?)


Spring ahead

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

The Answer: the Letter 'R'

(Can you solve this tricky numbers riddle?)


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Cruising along

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This brainteaser is hard because it seems 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.

The Answer: All the people were married

(If you can solve the secret word in this logic puzzle, you might be a genius.)



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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!

The Answer: Heroine

Good with numbers

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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!

The Answer: Bookkeeper

(Here is a math puzzle if you're feeling like a genius.)

Violent delights

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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.

The Answer: She took a picture of him and developed it in her dark room.

(Can you find the missing number in this puzzle?)

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The write stuff

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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.

The Answer: Pencil lead

Sibling squad

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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.

The Answer: Four sisters and three brothers

(Only ten percent of people can spot the difference in this picture. Can you?)

Say my name

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This hard riddle requires 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.

The Answer: Silence.

(Can you solve the world's first crossword puzzle?)

Math time

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You might start doing some elaborate fractions but this hard riddle is much more about word play than crunching the numbers. Think literally and the answer may just appear right before your eyes.

The Answer: IV, the Roman numeral for four is "half" (two letters) of the word five.

(If you're in the mood for more math, check out this math problem that's stumping the Internet.)

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Find the key

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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 that don't require locks?

The Answer: a Keyboard

(Can you guess which flag comes next in this puzzle?)

Beachy keen

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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.

The Answer: A towel

Literally speaking

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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.

The Answer: Eleven letters in "the alphabet"

(Here's another brain-twist—the alphabet used to have six more letters than it does now!)

Family affair

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Hard riddles work to trip you up and send you 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.

The Answer: A is D's aunt

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Line up

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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.

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

(Don't miss this brainteaser with another super hard answer.)

Yours or mine

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

The Answer: Your name

Color test

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Some riddles work by getting your brain to go through a series of associations so you get locked in and can't think of alternatives. Be careful with this riddle. 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.

The Answer: Water

(Do you think you're a crossword puzzle expert? Prove it!)

Number line

Toughest-Riddles-EverTatiana Ayazo/ RD.com
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 hard 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.

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

(Want some more wordplay? Here are 20 words that smart people mispronounce.)

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Out to lunch

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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.

The Answer: A Fishhook

Time bomb

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This hard riddle has 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.

The Answer: the Letter "M"

Easy peasy

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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.

The Answer: Incorrectly

(Check out how long it would take you to read the whole dictionary.)

Hand in hand

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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.

The Answer: Your left hand

(Can you figure out which airplane doesn't belong in this picture?)


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Daddy issues

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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.

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


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