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Hard Riddles With Answers

These hard riddles with answers are meant to trip you up. There’s no doubt that these will have your brain working at the fullest, maximum capacity if you hope to solve them.

These stumpers hit you with details from every angle and will challenge your brain and encourage you to think outside the box.

Some may be harder than others, and we have provided answers if you find them challenging. So, see if anyone you know has stellar problem-solving abilities by challenging them with these tricky riddles.

Let’s kick things off with the Poet’s Panel’s top ten picks of tricky riddles.

Best hard riddles.

Best Hard Riddles

Tricky riddles for the brain are like barbells for your biceps. They get you thinking, and as a result, you’re a little brighter.

envelope riddle.

1.) What word starts with E and ends with E but only has one letter?
An envelope.

Don’t you hate it when the answer seems obvious but only after you’ve read it? The key to answering this was interpreting the “one letter” portion.

Thumb puzzle.

2.) It’s shorter than the rest, but when you’re happy, you raise it like it’s the best. What is it?
A thumb.

Many tricky riddles’ answers can be found in everyday items you use daily — like the shortest digit on your hand — your thumb!

You carry it everywhere mystery.

3.) You can carry it everywhere you go, and it does not get heavy. What is it?
Your name.

Certain tricky riddles make use of some words more than others. These words and phrases include your name, shadow, a candle, a mirror, and wind.

fingerprints hard riddles..

4.) The more you take, the more you leave behind. What am I?

Ok, this is a tough one. I’d hesitate to guess over 99% of folks don’t answer this correctly unless they’ve heard it before.

See 65 challenging riddles for teens.

The more you see the less there is riddle.

5.) The more there is, the less you see. What am I?

If you stay patient with this one, it’s very answerable. The contradictory setup of this complex riddle is pervasive.

Super Hard Riddles.

Challenging Riddles

Sometimes, the answers to tricky riddles are more obvious than you think. Keep that in mind as you take on these challenges.

6.) What is full of holes but still holds a lot of water?
A sponge.

One-of-a-kind nouns seem to be a favorite for riddle questioners. No other easily identified object quite has the properties of a sponge. So, it’s a good riddle.

7.) A word I know contains six letters, removes one and has twelve remaining. What am I?

Riddles that feature letters are also a favorite. They can be very tricky. The key to answering this one is to focus on the number 12.

8.) You see a boat filled with people. You look again but don’t see a single person on the boat this time. Why?
The boat has not sunk. All the people on the boat are married.

Ah-ha! Words with multiple meanings, like single, help set up a good riddle.

See 73 Spring Riddles.

Barrel is hard riddle.

9.) A barrel of water weighs 60 pounds. What must you put in it for it to weigh 40 pounds?
A hole.

So hard when you first hear this one because when folks think of “putting in,” they think of something they’re adding to the equation. While a hole is added, it has a far different effect, as we all know.

10.) What word of five letters has only one left when two are removed?

It’s still difficult even if you started with the premise of finding a five-lettered word with “one” in it.

Riddles With Answers for Kids

These hard riddles for kids will create conversation and excitement.

11.) What has golden hair and stands in the corner?
A broom.

12.) I’m gone if you have it and show it to other people. What am I?
A secret.

13.) A bus driver goes the wrong way on a one-way street. He passes the cops, but they don’t stop him. Why?
He was walking.

14.) I speak without a mouth and hear without ears. I have nobody but come alive with the wind. What am I?
An echo.

15.) What word looks the same upside down and backward?

Tip: If you have some free time, put your noggin to good use by trying a few of these tricky riddles. They’ll keep your mind sharp.

Hard Riddles Meme

boat filled with people puzzler.

Short Hard Riddles

Short, hard riddles are sometimes easier to remember.

16.) How do football players stay cool during a game?
They stand next to the fans.

17.) What type of dress can never be worn?

18.) My rings are not of gold, but I get more as I get old. What am I?
A tree.

19.) What is at the end of a rainbow?
The letter W.

20.) What has ten letters and starts with gas?
An automobile.

21.) No sooner spoken than broken. What is it?

You might like Funny Never Have I Ever Questions.

Tricky Puzzlers

22.) How many bricks does it take to complete a building made of bricks?
One brick – “complete a building.”

23.) What spends all the time on the floor but never gets dirty?
Your shadow.

24.) How do you know carrots are good for your eyes?
You never see rabbits wearing glasses.

25.) What falls but never breaks? What breaks but never falls?
Day and Night.

You might like Difficult Math Puzzlers.

Difficult Riddles for Adults

Ok, put your grown-up pants on for these tricky riddles.

26.) A man goes out in heavy rain with nothing to protect him from it. His hair doesn’t get wet. How does he do that?
He’s bald.

27.) Mike and Pat are in a desert. They both have packs on. Pat is dead. Mike, who is alive, has his pack open. Pat has his pack closed. What is in the packs?

28.) What has four fingers and a thumb but is not living?
A glove.

29.) What has a heart that doesn’t beat?
An artichoke.

30.) I only lie down once – when I die. What am I?
A tree.

31.) I have four keys but no locks. I have space but no room. You can enter but can’t go inside. What am I?
A keyboard.

32.) Give me food, and I will live. Give me water, and I will die. What am I?

33.) How do you fit ten horses into nine stalls?
[t] [e] [n] [h] [o] [r] [s] [e] [s]

34.) What comes in a minute, twice a moment, but never in a thousand years?
The letter M.

You might like: Tricky Riddles With Answers

Hardest Riddles

We’ve raised the bar from tricky riddles to the hardest. Good luck; you’ll need it.

35.) You are my brother, but I am not your brother. Who am I?
I am your sister.

36.) How can you drop a raw egg from a height onto a concrete floor without cracking it?
Concrete floors are tough to crack.

37.) What can travel worldwide while staying in a corner?
A stamp.

38.) What goes up a chimney down but not down a chimney up?
An umbrella.

39.) There are two sisters. One gives birth to the other, and she, in turn, gives birth to the first. Who are the two sisters?
Day and night.

40.) What happens once in a minute, twice in a moment, but never in a thousand years?
The letter “M.”

Note: There’s no “show answer” button immediately below the query to make it quicker. It’s listed right below.

Check out: What Am I? Challenge

Real Stumpers

Hard riddles are fun to share with kids and family. Jot down a few and put your group to the test.

41.) A rooster lays an egg at the very top of a slanted roof. Which side will the egg roll off on?
Neither – roosters don’t lay eggs.

42.) Take away the whole, and some remain. What is it?
The word “wholesome.”

43.) Forward I am heavy, but backward I am not. What am I?
Forward I am ton; backward I am not.

44.) What always ends everything?
The letter G.

45.) Where can you finish a book without finishing a sentence?

46.) What has only two words but thousands of letters?
A post office.

Check out Trick Questions.

Onerous, Hard Riddles

47.) It is an insect, and the first part of its name is the name of another insect. What is it?

48.) From the beginning of eternity to the end of time and space, to the beginning of every end and every place. What am I?
The letter E.

49.) What is as big as an elephant but weighs nothing?
The shadow of an elephant.

50.) You can see me in water, but I never get wet. What am I?
A reflection.

51.) What has a head, and a tail, is brown, and has no legs?
A Penny.

Check out: 125+ Who is Most Likely To Questions.

Testy Brainteasers

52.) Which part of a boat does a shopaholic like the most?
The sail.

53.) Name a 7-letter word, from which you will have one left if you take out four letters.

54.) What can’t be burned in a fire nor drowned in the water?
Ice. It melts instead of burning in a fire and floats in water.

55.) If you are running a race and passing the person in second, what place are you in?
Second place.

56.) John walks into a bar and asks for a glass of water. The bartender then shoots the ceiling with a gun. John says thank you and walks out. Why did John want the water?
He had hiccups. The bartender used the surprise method to shock him out of his hiccups.

Hard Riddles with Simple Answers

Be patient when answering these complex questions; the answers might just come to you.

57.) What can fill an entire room without occupying any space?

58.) What exists when one person has it but ceases to exist when another person gets it?
A secret.

59.) What’s black when you get it, red when you use it, and white when you’re all through with it?

60.) Bennett pushed his car into a hotel and lost his fortune. How?
He was playing the game Monopoly.

61.) One knight, a ninja, and a pirate are on a boat. The boat crashes. The pirate jumps off; first, the ninja jumps off second, and who jumps off third?
The knight. Folks think the opening reads, “One night, …” not “One knight;…”

62.) Take off my skin – I won’t cry, but you will! What am I?
An onion.

63.) If there are three cups of sugar and you take one away, how many do you have?
One is the only one you took away; that is all you have. The rest remain where there were.

64.) How do you eat an elephant?
One bite at a time.

65.) I have one letter, but my name is spelled with eight. What am I?
An envelope.

66.) What flowers can be found between the nose and the chin?
Tulips – get it? “Two lips.”

Hard Riddles Quiz

No one said this was going to be easy. Test your smarts on this collection of hard riddles.

67.) What is at the beginning of eternity and at the end of time is in every race but is always last in line?
The letter E.

68.) When you need me, you throw me away. When you don’t need me, you bring me back. What am I?
An anchor.

69.) You do not want me when you don’t have me, but you don’t want to lose me when you have me. What am I?
A lawsuit.

70.) Walk on the living; they don’t even mumble. Walk on the dead, they mutter and grumble. What are they?

71.) The man who invented it doesn’t want it for himself. The man who buys it doesn’t buy it for himself. And, the man who needs it doesn’t know he needs it. What is it?
A coffin.

Brain Twisters

72.) Say my name, and I am no more. What am I?

73.) A man is driving along and sees three doors: a diamond, ruby, and emerald. Which does he open first?
His car door.

74.) Each day, many people from around the world visit me; however, they usually only stay for a few minutes. I am considered by many to be very dirty, yet few people would want to live without me. And whenever people come to see me, they show a part of themselves that they rarely show to others. What am I?
A toilet.

75.) First, I threw away the outside. Then, I cooked the inside. And then I ate the outside and threw away the inside. What am I?

76.) What’s the coolest letter in the alphabet?
The letter B. AC surrounds it.

77.) I have keys that open, no locks and space but no room. You can enter but can’t go in. What am I?
A keyboard.

78.) What can you hold in your left hand but not your right?
Your right elbow.

Funny Hard Riddles

When you’re using your mind, it helps to have a few laughs along the way. These funny, hard riddles should accomplish that.

79.) What is brown and sticky?
A stick.

80.) How many apples grow on a tree?
All apples grow on trees. (Sorry, don’t hate me.)

81.) What ancient invention still used in parts of the world today enables people to see through walls?
A window.

Complicated Sticklers

82.) What word in the English language satisfies this? The first two letters signify a male, the first three letters indicate a female, the first four letters signify a great, and the entire word means a great woman.

83.) A man drove from New York City to Los Angeles in four days. At the end of his trip, he discovered that one of his tires had been punctured. How was he able to make the drive?
The tire was the car’s spare tire.

84.) Trevor pointed to a girl in the street and said, “She is the daughter of my grandmother’s only child.” What is the girl’s relationship with Trevor?
She is Trevor’s sister.

85.) What kind of fruit can you use as a straw?
A strawberry! (Ok, that one wasn’t very complicated.)

86.) A woman shoots her husband, then holds him underwater for five minutes. Next, she hangs him. Right after, they enjoy a lovely dinner.
She took a photo of him and developed it in the darkroom.

Difficult Riddles

87.) Where does today come before yesterday?
The dictionary.

88.) What English word has three consecutive double letters?

89.) What is seen in the middle of March and April that can’t be seen at the beginning or end of either month?
The letter R.

90.) What can you hold in your right hand but never in your left?
Your left hand.

91.) George, Helen, and Steve are drinking coffee. Bert, Karen, and Dave are drinking soda. Is Elizabeth drinking coffee or soda?
Elizabeth is drinking coffee. The letter E appears twice in her name, as in the names of the others drinking coffee.

92.) What English word retains the same pronunciation, even after you take away four of its five letters?

93.) Thanks to texting and email, I don’t get used to as much as I used to.
Pencil lead.

Tough Riddles

94.) It can’t be touched and can’t be felt. It can’t be seen, heard, or smelt. And it lies behind stars and under hills and any empty holes it fills. It comes early and follows after, ends life, and kills laughter.

95.) An electric train is headed east. Where does the smoke go?
Electric trains don’t produce any smoke.

96.) I have a single eye but can’t see. What am I?
A needle.

97.) Which is heavier: a ton of sand or a ton of feathers?
They’re the same. They both weigh a ton.

98.) I can shave daily, but my beard never changes. What am I?
A barber.

99.) There is a single-story blue house where everything is blue; the doors, windows, couch, television, kitchen, etc., are blue. What color is the carpet on the stairs in this house?
There are no stairs; it’s a one-story house.

100.) If two’s a company, and three’s a crowd, what are four and five?

101.) Which letter of the alphabet has the most water?
The letter C.

Fun Riddles

102.) What kind of room has no door or windows?
A mushroom.

103.) 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?
Water. (Not milk.)

104.) Without a bridle or a saddle, across a thing, I ride a straddle. And those I ride, by the help of me, though almost blind, are made to see. What am I?

105.) You are in a dark room with a box of matches. In the room are a candle, a kerosene lamp, and a fireplace. What do you light first?
The match.

106.) What word am I? 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?

Tricky Problems

107.) Poor people have it. Rich people need it. If you eat it you die. What is it?

108.) What is 3/7 chicken, 2/3 cat, and 2/4 goat?

109.) Throw away the outside and cook the inside, then eat the outside and throw away the inside. What is it?
Corn on the cob.

110.) What is always at the end of a rainbow?
The letter W.

111.) What grows up as it grows down?
A goose.

112.) What can a child make but never see?
Noise. (And some are quite accomplished at this.)

113.) What has 13 hearts but no other organs?
A deck of cards.

See these Fun Riddles for Kids.

Common Sense Tips For Solving Hard Riddles

These suggestions might help you solve more.

A.) Think long and hard before you answer

These tricky riddles are difficult for a reason. Most of the time, the first answer that comes to mind is wrong. Riddles are frequently constructed so that the apparent response isn’t the solution. This is called misdirection. So, pause, and consider alternatives before blurting out your answer.

B.) Practice solving many hard riddles

Much like your muscles’ repetitive use helps us build muscle, putting your brain to work frequently on solving riddles and puzzles will help your lateral thinking and problem-solving abilities.

C.) Look for patterns

After you’ve read through the solutions to 50 or so tricky riddles, you’ll note some patterns emerging. For example, there are the “Letter Solution” type riddles. Here’s an example: What comes once in a minute, twice in a moment, but not once in a thousand years? The answer: The letter M. Or, What is at the end of a rainbow? Answer: The letter W.

There’s also the “Solution Built Into the Riddle” approach. For example, “You’re the bus driver, and you have seven passengers. One got off on Washington. Two got on at Main Street, and three exited on Lincoln. What’s the bus driver’s name? The Answer: Your name (because remember “You’re the bus driver).

Conundrums incorporate puns and word double meanings into the riddle and the solution, or sometimes both. Here’s an example: How do football players stay cool during a game? Answer: They stand next to the fans.

Understanding these patterns will help you tremendously, as many challenging riddles are similar in structure and approach.

D.) Break down the riddle question into parts

Sometimes, it helps break down multi-sentence, tricky riddles into parts: beginning, middle, and end. Don’t be afraid to ask the riddler to repeat tricky riddles – even several times if necessary. Listening intently may help you solve it.

E.) Consider a wide selection of possible answers

Don’t lock into what you think is the correct answer until you’ve considered many options.

F.) Be careful about assumptions

Many hard riddles play to stereotypes. For example, only men are doctors. Question everything, and you might get to the solution!

G.) For hard riddles, it helps to see the mystery in writing

Look for clues everywhere. A particular pronoun might help you get to the correct answer. The opening line of challenging puzzles is frequently where a vital clue is given. Read and re-read it.


Here are some frequently asked questions about riddles.

What is the definition of “riddle”?

A question designed to mislead or puzzle. A riddle is typically posed as a problem to be solved by guessing. Example: What can travel around the world while staying in a corner? Answer: A stamp.

What is the world’s oldest known riddle?

The Ancient Sumer civilization, living in what is now known as Iraq, told this riddle some 4,000 years ago: “There is a house. One enters it blind and comes out seeing. What is it? Answer: A school. (This speaks to the value Sumerians placed on education.)

What is the most famous riddle?

The riddle of the Sphynx: “What goes on four legs in the morning, on two legs at noon, and three legs in the evening?” Answer: A human. Four legs refer to a baby crawling, two to midlife walking, and three to old age walking using a cane.


And that’s a wrap! You might have been surprised at just how easy some of these challenging, hard riddles can be. The more exposure you have to hard riddles, the easier it is to answer new ones.

Test your family and friends and see how long it takes them to solve these. Save the toughest for your closest friends or older brother.

By Michael O’Halloran

O’Halloran is the editor of Greeting Card Poet and has co-authored four trivia books under the Smart Attack brand.


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