These hard riddles 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 not only challenge your brain but will also encourage you to think outside the box.
Some may be harder than others, and if you found them difficult, we have provided answers. So, see if anyone you know has stellar problem-solving abilities by challenging them with these difficult riddles.
Let’s kick things off with the Poet’s Panel top ten picks of hard riddles.
Best Hard Riddles To Stump The Brain
Hard riddles for the brain are like barbells for your biceps. They get you thinking, and as a result, you’re a little smarter.
1.) What word starts with E and ends with E but only has one letter in it?
Don’t you hate it when the answer seems obvious, but only after you’ve read it. The key to answering this one was interpreting the “one letter” portion.
2.) It’s shorter than the rest, but when you’re happy, you raise it like it’s the best. What is it?
Many tricky riddles’ answers can be found in common items that you use every day — like the shortest digit on your hand — your thumb!
3.) You can carry it everywhere you go, and it does not get heavy. What is it?
Certain difficult riddles make use of some words more than others. Some of these words and phrases include your name, shadow, a candle, a mirror, and wind.
4.) The more you take, the more you leave behind. What am I?
Ok, this is a real tough one. I’d hesitate to guess over 99% of folks don’t answer this correctly unless they’ve heard it before.
5.) The more there is, the less you see. What am I?
If you stayed patient with this one, it’s very answerable. The contradictory setup of this hard riddle is pervasive.
More of the Best Really Hard Riddles
Sometimes the answers to hard 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?
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, six letters it contains, removes one letter, and twelve remains. 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 this time you don’t see a single person on the boat. 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.
9.) A barrel of water weighs 60 pounds. What must you put in it for it to weigh 40 pounds?
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 well all know.
10.) What word of five letters has only one left when two letters are removed?
It’s still difficult even if you started with the premise of finding a five-lettered word with “one” in it.
Hard Riddles To Trick Your Mind Video
Difficult Riddles With Answers for Kids
These hard riddles for kids will create lots of conversation and excitement.
11.) What has golden hair and stands in the corner?
12.) If you have it and you show it to other people, I’m gone. What am I?
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?
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 hard riddles. They’ll keep your mind sharp.
Hard Riddles Meme
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?
19.) What is at the end of a rainbow?
The letter W.
20.) What has ten letters and starts with gas?
21.) No sooner spoken than broken. What is it?
You might like Funny Never Have I Ever Questions.
More Riddle Examples
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?
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.
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Difficult and Hard Riddles for Adults
Ok, put your grown-up pants on for these hard 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 is 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 thumb, but it is not living?
29.) What has a heart that doesn’t beat?
30.) I only lie down once – when I die. What am I?
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?
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 in a moment, but never in a thousand years?
The letter M.
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We’ve taken the bar from hard riddles and raised it 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 around the world while staying in a corner?
38.) What goes up a chimney down, but not down a chimney up?
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 for you. It’s listed right below.
Check out: What Am I? Challenge
Good Hard Riddles: 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 is the egg going to 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 at all?
The shadow of an elephant.
50.) You can see me in water, but I never get wet. What am I?
51.) What has a head, a tail, is brown, and has no legs?
Check out: 125+ Who is Most Likely To Questions.
52.) Which part of a boat does a shopaholic like the most?
53.) Name a 7 letter word, from which if you take out 4 letters, you will have 1 left?
54.) What can’t be burned in a fire nor drowned in the water?
Ice. It melts instead of burning in a fire, and it floats in water.
55.) If you are running a race and pass the person in second, what place are you in?
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 hard questions, and the answers might just come to you.
57.) What can fill an entire room without taking up any space?
58.) What exists when one person has it but ceases to exist when another person gets it?
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 of 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?
63.) If there are three cups of sugar and you take one away, how many do you have?
One, as that is the only one you took away, and that is all that 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?
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?
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?
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?
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 all over the world come and visit me, however, they usually only stay for a couple of 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?
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?
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?
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?
82.) What word in the English language satisfies this? 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?
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.)
Common Sense Tips To Solving Hard Riddles
These suggestions might help you solve more.
A.) Think long and hard before you answer
These hard 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 obvious response isn’t the solution. This is called misdirection. So, pause, and consider alternatives before blurting out your answer.
B.) Practice by 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 hard 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 7 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 hard riddles are similar in structure and approach.
D.) Break down the riddle question into parts
Sometimes, it helps break down multi-sentence, hard riddles into parts: beginning, middle, and end. Don’t be afraid to ask the riddler to repeat hard 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 just might get to the solution!
G.) For hard riddles, it helps to see the riddle in writing
Look for clues everywhere. A particular pronoun might help you get to the correct answer. The opening line of hard riddles is frequently where a strong 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 legs to midlife walking, and three legs 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 Mike O’Halloran
O’Halloran, the editor of Greeting Card Poet, co-authored four trivia books under the Smart Attack line.
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