20 Challenging riddles that are sure to test your brain

The fastest way to make some people sweat is to put a complicated equation in front of them. But a particularly clever and mysterious riddle can remain puzzling for others for days. And those struggling with it will find it much harder to get a riddle out of their heads.

Because it's easy to give up on something that seems completely inscrutable, but a riddle usually sounds simple until somebody tries to figure it out. But, of course, that makes it all the more satisfying when the answer does finally reveal itself. And there are plenty of opportunities for that satisfaction right here!

What gets wetter as it dries?

Nazaré Celebrates Surfing On Giant Waves
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Guillaume Pinon/NurPhoto via Getty Images

A. A wave

B. A sponge

C. A surfer

D. A towel

Answer: A towel

While this riddle initially brings to mind something that dries itself, the only way it makes sense is if the item in question is drying something else. Thus, a towel gets wetter as it dries.

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What is a one-seeded fruit that fills calendars everywhere?

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A. Moon fruit

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B. Plums

C. Dates

D. Grapes

Answer: Dates

A typical calendar may not be filled with dried fruit that comes from the Middle East, but it is certainly full of dates. It's one of those riddles that seems obvious once the right answer comes to mind.

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What has to be broken before you can use it?

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A. A package

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B. The human brain

C. A toolbox

D. An egg

Answer: An egg

No matter how you like your eggs, there's no way to get at the nutrients inside without breaking them first. The only time most of us can do something with an egg without breaking it is Easter.

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What flies when it's born, lies while living, and runs while dead?

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A. A snowflake

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B. A mosquito

C. The tide

D. A speck of dust

Answer: A snowflake

If this one seems like nonsense, let's break it down. A snowflake is born in the sky and lies on the ground when it's intact or "alive." But when it "dies," it melts and, thus, becomes a little puddle of running water.

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A man with no hat or umbrella didn't get any hair wet in the rain. Why?

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A. His raincoat had a hood

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B. He was bald

C. His route home was under a series of awnings

D. He was just lucky

Answer: He was bald

While it's not hard to see how someone could argue these other possibilities, the fact is that the most surefire way not to get your hair wet is not to have any.

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I have a head with no body, but I do have a tail. What am I?

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A. A bizarre genetic experiment

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B. An idea

C. A coin

D. A comet

Answer: A coin

A coin may not have a body to speak of, but we know that we can pick heads or tails when we flip one. And while whose head is on the coin varies from place to place, it's usually somebody.

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What will never speak unless you say something?

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Parrots and owls of different species are on display at a bird show at Yarmouk district of Kuwait City, Kuwait on March 11, 2023.
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A. A parrot

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B. An echo

C. A robot

D. An annoying younger sibling

Answer: An echo

While all of the other options can potentially be pretty noisy when you leave them alone, the same is not true for an echo. The only way one can be heard is by repeating a noise someone else made.

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What starts with an M, ends with an X, and is packed with letters?

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A. Matrix

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B. Metathorax

C. Multiplex

D. Mailbox

Answer: Mailbox

The word may not be particularly long or complicated, but the thing the word is describing can certainly find itself packed with letters. Remember, the wordplay in a lot of these are intended to throw people off.

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What goes up and down but doesn't move?

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A. A staircase

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B. An elevator

C. The stock market on a frozen screen

D. The concept of time

Answer: A staircase

Although we tend to describe a staircase that leads up or down as "going" there, the only ones who are truly moving are the people who use them. Language is funny.

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What's light as a feather but can't usually be held for five minutes?

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A. A hot coal

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B. A hyperactive mouse

C. A breath

D. A paper airplane on fire

Answer: A breath

While it would certainly be difficult to hold these other things for any length of time, our bodies really don't like it when we try to hold our breath for five minutes. I'd recommend taking my word for it.

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Where does today come before yesterday?

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A. In Back To The Future

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B. In a dictionary

C. In an alternate universe

D. In our dreams

Answer: In a dictionary

While it's impossible to experience today before we experience the day before it, that's not the case in one special book that plays by different rules. Once spelling is taken into account instead of chronology, the dictionary makes this seemingly impossible feat mundane.

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What tree is carried in every hand?

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A. Pine

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B. Bonzai

C. Palm

D. Elm

Answer: Palm

While our first thoughts may lead us to imagine the smallest possible trees, the devious wordplay of these riddles strikes again. Every hand may not strictly have a tree in it, but it does have a palm.

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What gets bigger when more of it is taken away?

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The Thinker sculpture at The Rodin Museum.
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John Greim/LightRocket via Getty Images
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A. Life

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B. Love

C. Taffy

D. A hole

Answer: A hole

Although it goes against most instincts to picture digging a hole as taking part of it away, it's also hard to describe the action any other way without using the word "dig." But of course, shoveling away more dirt only makes the hole bigger.

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It belongs to you, but other people use it more. What is it?

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In this picture taken on February 6, 2023 a pigeon approaches to land on the face of the Great Sphinx at the Giza Pyramids necropolis on the outskirts of the Egyptian capital.
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A. Your Playstation

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B. A pack of gum in a classroom

C. A board game

D. Your name

Answer: Your name

Unless you make a habit of talking in the third person, there's a very good chance that other people will use your name more often than you do as your life goes on. You're certainly welcome to start talking in the third person to spite me, though.

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What is black when it's clean and white when it's dirty?

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A. An eight-ball

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B. A black dog

C. A blackboard

D. A black hole

Answer: A blackboard

Although many people grew up looking at green chalkboards in school instead of black ones, they typically weren't given this specific name. Nonetheless, the whiter they become, the more in need of an eraser they are.

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I have branches but no leaves, trunk, or fruit. What am I?

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Dead trees stand in the devastated Harz forest on April 10, 2023 near Wernigerode, Germany.
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A. A bank

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B. A burnt shrub

C. A dryad

D. A tumbleweed

Answer: A bank

Indeed, the answer to this riddle that sounds like it has everything to do with plants is the least natural thing on the list. A bank can have many branches, but you're not likely to find leaves, fruit, or tree trunks in any of them.

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How do you say "hard water" with only three letters?

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A. Hwr

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B. Wet

C. Ice

D. Frz

Answer: Ice

Yes, it turns out that this task doesn't take the kind of thinking that kids used to apply when they entered their name next to their high score in an arcade game. The word "ice" does the job all on its own.

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I shave every day, but my beard stays the same. How?

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A. You only touch it up

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B. You have super fast-growing hair

C. A wizard did it

D. You're a barber

Answer: You're a barber

That's right, the barber in this riddle never said anything about shaving themselves. The simplest answer is often the right one, but that still means somebody has to think of it first.

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

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A. Money

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B. Footsteps

C. Glitter

D. Food

Answer: Footsteps

Although we take steps, the irony is that we're always leaving either the imprint or the sound of our steps behind when we do. Who decided to describe footsteps that way, anyway?

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What is easy to lift but hard to throw?

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A. A cat

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B. Slime

C. A feather

D. A bean bag chair

Answer: A feather

Unlike with most of these other options, there aren't any real consequences for trying to throw a feather. But if you try it, you'll no doubt find that it's not going to go where you want.