Hard Riddles That'll Leave You Totally Stumped

These brain teasers will sharpen your focus and lift you out of your brain fog.


When was the last time you tried to answer a riddle? When we're kids, riddles are something we seem to come across constantly, challenging us to reframe our assumptions, look for alternate meanings of a question, or think more creatively. But the brain-flexing value of a good riddle doesn't go away as we grow up and no matter our age, it's worthwhile to challenge ourselves to a tricky riddle now and then. So here, we offer 30 hard riddles that we hope will trip you up and sharpen your focus.

1. Getting personal

Riddle: This belongs to you, but everyone else uses it.

We're starting out with a relatively easy one. Don't get tripped up thinking this is an actual object…

Answer: Your name

2. Wooden delivery

Riddle: I come from a mine and am surrounded by wood. I help others to express themselves. What am I?

Thanks to texting and email, I don't get used as much as I used to.

Answer: Pencil lead

3. A common mistake

Riddle: Which word in the dictionary is always spelled incorrectly?

The answer is right there in the question.

Answer: "Incorrectly"

4. Where in the world

Riddle: I have cities, but not houses. I have mountains, but no trees. I have coasts, but no sand. What am I?

Think "bigger picture" with this one.

Answer: A map

5. Read all about it

Riddle: What English word has three consecutive double letters?

The answer to this actually refers to someone who themselves loves numbers. Some claim there are actually two words in the English language that have three consecutive double letters—the other being "woollen,"—double "u," double "o" and double "l."

Answer: Bookkeeper

Riddle: You're in a dark room with a candle, a wood stove, and a gas lamp. You only have one match, so what do you light first?

6. Hard to see

Riddle: You're in a dark room with a candle, a wood stove, and a gas lamp. You only have one match, so what do you light first?

This one is obvious when you know what to look for.

Answer: The match

7. An illuminating question

Riddle: 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.

"Quick" does not mean that it is moving toward you.

Answer: A candle

8. Sail away

Riddle: 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?

Focus on the word "single" to figure out the answer to this one.

Answer: All the people were married.

9. Don't know what you got til it's gone

Riddle: What gets bigger the more you take away?

Good luck digging yourself out of this one.

Answer: A hole

10. To have and to hold

Riddle: What can you hold in your right hand but never in your left?

The answer is right there in front of you.

Answer: Your left hand

11. Key question

Riddle: I have keys but no locks. I have space but no room. You can enter, but you can't go outside. What am I?

If you're like most modern workers, you spend a lot of time on this during the typical day.

Answer: A computer keyboard

12. Well worn

Riddle: It's best to put this coat on wet.

This one's easy once you realize it's not referring to an item of clothing.

Answer: A coat of paint

13. Gotta hand it to you

Riddle: What has four fingers and a thumb but isn't alive?

No, the answer is not "hand."

Answer: A glove

14. Springtime

Riddle: What is seen in the middle of March and April that can't be seen at the beginning or end of either month?

The trick here is that this answer has nothing to do with the time of year when the months fall, but the words themselves.

Answer: The letter "R"

15. Violent imagery

Riddle: A woman shoots her husband. She plunges him underwater for several minutes, then hangs him. Right after, they enjoy a lovely dinner. What happened?

When we says "him" we aren't actually referring to a person.

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

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?

16. Family time

Riddle: 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?

Don't let all this talk of "brothers" and "father" might get you stuck thinking about male relatives.

Answer: A is D's aunt.

17. A good cut

Riddle: A butcher stands six feet and one inch tall and wears size 12 shoes. What does he weigh?

Pay close attention to the phrasing of the question—there's a reason it didn't ask, "How much does he weigh?"

Answer: Meat

18. A filthy question

Riddle: How much dirt is in a hole that measures four feet by four feet by five feet?

Don't let the specific numbers fool you—the answer would be the same no matter what the hole measured.

Answer: None

19. Looking for inspiration

Riddle: What word in the English language fulfills all the following criteria: The first two letters signify a male, the first three letters signify a female, the first four letters signify a great, while the entire word signifies a great woman.

Think Wonder Woman…

Answer: Heroine

20. Some find it blissful

Riddle: What disappears the moment you say its name?

It's also something you can "break" the moment you speak.

Answer: Silence

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21. I hear that

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

Don't let the description of body parts throw you—the answer is definitely not a person or animal. Focus more on the "wind" to get to the answer.

Answer: An echo

22. One after another

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

To figure this one out, think less about letters than numbers.

Answer: ENT. Each letter is the first letter of a number beginning with One. So what comes after six and seven? Eight, nine, and ten.

23. Number crunching

Riddle: How is seven different from the rest of the numbers between one and ten?

Sort of the reverse of the previous riddle, this one tricks you by making you think that it's a number question, when it's actually about words.

Answer: Seven is the only one with two syllables.

24. Time is on my side

Riddle: What comes once in a minute, twice in a moment, but never in a thousand years?

Think less about the meaning of the words than the words themselves.

Answer: The letter "M"

25. Psst…you'll never guess it

Riddle: If you have me, you want to share me. If you share me, you don't have me. What am I?

It's something you share with friends.

Answer: A secret

I only have two words but thousands of letters, what am I?

26. Signed, sealed, delivered

Riddle: I have only two words but thousands of letters. What am I?

The meaning of "letters" is the important one to focus on here.

Answer: Post office

27. Eat or be eaten

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

The "you" in this instance is an animal.

Answer: A fishhook

28. Numerous possibilities

Riddle: Turn me on my side, and I am everything. Cut me in half and I am nothing. What am I?

Consider the concept of shape.

Answer: The number eight (8)

29. World traveler

Riddle: What can travel all around the world while remaining stuck in a corner?

It might also end up finding itself in a collection.

Answer: A stamp

30. Headless

Riddle: I have a neck and no head, two arms and no hands? What am I?

C'mon, you know this one by now.

Answer: A shirt

And for more tips to stay sharp, here are 5 Words That Will Make You Sound Smarter Instantly.

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