The Hardest Riddles

Riddle: Say my name

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

Riddle: Math time

How can the number four behalf 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.

Riddle: Find the key

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 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?

Answer: A keyboard

Riddle: Beachy keen

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. 

Riddle: Literally speaking

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”

Riddle: Family affair

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 aunt.

Riddle: Line up

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.).

Riddle: Yours or mine

This belongs to you, but everyone else uses it. 

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.

Answer: Your name.

Riddle: Color test

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?

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.

Answer: Water

Riddle: Out to lunch

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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