When was the last time you challenged yourself with a riddle? These puzzles are a fun way of testing your critical thinking skills, encouraging you to examine your assumptions, look for alternate meanings, and think more creatively. The brain-flexing value of a good riddle doesn't go away as you grow up either—brain teasers can help you stay sharp as you grow older. So read on for 95 hard riddles that will get your gears turning. Don't worry, answers are included!
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Hardest Riddles Ever
Best Life- Riddle: I speak without a mouth and hear without ears. I have no body, but I come alive with wind. What am I?
- 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.
- Riddle: I come from a mine and am surrounded by wood. I help others to express themselves. What am I?
- Riddle: What is brown and has a tail, a head, and no legs?
- Riddle: If all Wibbles are Criggles, all Borkins are Kwumblins, no Hoggles are Borkins, and all Criggles are Borkins, is it true that all Borkins are Criggles?
- Riddle: What English word has three consecutive double letters?
- Riddle: A bus driver goes the wrong way down a one-way street. He passes the cops, but they don’t stop him. Why?
- Riddle: Name the next three letters in this combination: OTTFFSS.
- Riddle: There came a bird featherless and sat on the trees leafless. There came a maiden speechless and ate the bird featherless, from off the trees leafless. What is it?
- Riddle: You don't know me yet, but you always miss me when I'm gone. What am I?
- Riddle: Poor people have it. Rich people need it. If you eat it you die. What is it?
- Riddle: I can fly but have no wings. I cry but have no eyes. What am I?
- Riddle: Sam is outside a shop. She can't read the signs, but she knows she needs to go in to make a purchase. What store is she at?
- Riddle: What walks on four feet in the morning, two in the afternoon, and three at night?
Answer: An echo.
Answer: A candle.
Answer: Pencil lead.
Answer: A penny
Answer: No.
Answer: Bookkeeper.
Answer: He was walking.
Answer: ENT. Each represents the first letter of a number in a sequence beginning with "one." So what comes after six and seven? Eight, nine, and ten.
Answer: Snow.
Answer: Time.
Answer: Nothing.
Answer: A cloud.
Answer: An eyeglass store.
Answer: A man. The times of day represent a lifetime. He crawls as a baby, walks as an adult, and walks with a cane as an elderly man.
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Short, Hard Riddles
Best Life- Riddle: I have only two words but thousands of letters. What am I?
- Riddle: What can travel all around the world while remaining stuck in a corner?
- Riddle: What can you hold in your right hand but never in your left?
- Riddle: What has many teeth but cannot bite?
- Riddle: You go at red and stop at green. What am I?
- Riddle: How much dirt is in a hole that measures four feet by four feet by five feet?
- Riddle: What can you fill with empty hands?
- Riddle: What disappears the moment you say its name?
- Riddle: What kind of coat is best to put on wet?
- Riddle: What type of cheese is made backward?
- Riddle: What is the one thing everyone can agree is between heaven and earth?
- Riddle: I can make sounds, but I cannot be played. What am I?
- Riddle: I am higher without a head. What am I?
- Riddle: I have 13 hearts but no lungs or stomach. What am I?
- Riddle: I am easy to lift but hard to throw. What am I?
- Riddle: When is "L" greater than "XL"?
Answer: The post office.
Answer: A stamp.
Answer: Your left hand.
Answer: A comb.
Answer: A watermelon.
Answer: None; holes are empty.
Answer: Gloves.
Answer: Silence.
Answer: A coat of paint.
Answer: Edam.
Answer: The word "and."
Answer: Your voice.
Answer: A pillow.
Answer: A deck of cards.
Answer: A feather.
Answer: When you're using Roman numerals.
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More Tricky Riddles for Adults
Best Life- Riddle: Without a bridle or a saddle, across a thing, I ride a-straddle. And those I ride, by help of me, though almost blind, are made to see. What am I?
- Riddle: George, Helen, and Steve are drinking coffee. Bert, Karen, and Dave are drinking Pepsi. Following this pattern, is Elizabeth drinking coffee or soda?
- Riddle: 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?
- Riddle: If you have me, you want to share me. If you share me, you don't have me. What am I?
- Riddle: David's father has three sons: Snap, Crackle, and _____?
- Riddle: My thunder comes before the lightning. My lightning comes before the clouds. My rain dries all the land it touches. What am I?
- Riddle: I have cities but not houses. I have mountains but no trees. I have coasts but no sand. What am I?
- Riddle: I am something people love or hate. I change people's appearances and thoughts. If a person takes care of themself, I will go up even higher. Some people might want to try and hide me, but I will show. No matter how hard people try, I will never go down. What am I?
- 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?
- Riddle: A woman was born in 1975 and died in 1975. At the age of her death, she was 22 years old. How is this possible?
- Riddle: Four cars come to a four-way stop, each coming from a different direction. They can’t decide who got there first, so they all go forward at the same time. All four cars go, but none crash into each other. How is this possible?
- 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?
- 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?
- 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?
- Riddle: A butcher stands six feet and one inch tall and wears size 12 shoes. What does he weigh?
- Riddle: Three different doctors said that Paul is their brother yet Paul claims he has no brothers. Who is lying?
- Riddle: How can you physically stand behind your father while he is standing behind you?
Answer: Eyeglasses.
Answer: Coffee, just like all the other names with two E's. Those with one "E" drink Pepsi.
Answer: Water.
Answer: A secret.
Answer: David.
Answer: A volcano.
Answer: A map.
Answer: Age.
Answer: The match.
Answer: 1975 refers to the hospital room number, not the year.
Answer: They all made right-hand turns.
Answer: A computer keyboard.
Answer: She took a picture of him and developed it in her dark room.
Answer: A is D's uncle.
Answer: Meat.
Answer: No one is lying because the three doctors are Paul's sisters.
Answer: By standing back-to-back with him.
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Math Riddles for Adults
Best Life- Riddle: When Billy is asked how old he is, he replies, "In two years, I will be twice as old as I was five years ago." How old is he?
- Riddle: How is seven different from the rest of the numbers between one and 10?
- Riddle: Turn me on my side, and I am everything. Cut me in half, and I am nothing. What am I?
- Riddle: A girl has as many brothers as sisters, but each brother has only half as many brothers as sisters. How many brothers and sisters are there in the family?
- Riddle: Two girls were born to the same mother, on the same day, at the same time, in the same month, and in the same year—but they're not twins. How is this possible
- Riddle: A barrel of water weighed 60 pounds. Someone put something in it, and now it weighs 40 pounds. What did the person add?
- Riddle: I am an odd number. Take away a letter, and I become even. What number am I?
- Riddle: TEN = 20, 5, 14. MEN = 13, 5, 14. Using the same logic, what do WOMEN equal?
- Riddle: What would a math teacher be doing with a piece of graph paper?
- Riddle: How do eight eights add up to one thousand?
- Riddle: Mr. Taylor has four daughters and each has a brother. In total, how many children does Mr. Taylor have?
- Riddle: If an electric train is moving north at 55 mph and the winds blowing east at 70 mph, which way does the smoke blow?
- Riddle: What is 3/7 chicken, 2/3 cat, and 1/2 goat?
- Riddle: If a zookeeper had 100 pairs of animals in her zoo, and two pairs of babies are born for each one of the original animals, then (sadly) 23 animals don't survive, how many animals do you have left in total?
Answer: 12 years old.
Answer: Seven is the only one with two syllables.
Answer: The number eight.
Answer: Four sisters and three brothers.
Answer: The girls are triplets.
Answer: A hole.
Answer: Seven.
Answer: WOMEN = 23, 15, 13, 5, 14. The numbers represent the letter's position in the English alphabet.
Answer: Plotting something.
Answer: 888 + 88 + 8 + 8 + 8 = 1000.
Answer: Five children because all of his daughters have the same brother.
Answer: An electric train doesn't emit smoke.
Answers: Chicago.
Answer: 977 animals (100 x 2 = 200; 200 + 800 = 1000; 1000 – 23 = 977).
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Funny Riddles
Best Life- Riddle: Who spends the day at the window, goes to the table for meals, and hides at night?
- Riddle: Which word in the dictionary is always spelled incorrectly?
- Riddle: It belongs to you, but everyone else uses it.
- Riddle: First you eat me, then you get eaten. What am I?
- Riddle: What color is the wind?
- Riddle: If two snakes marry, what will their towels say?
- Riddle: Which fish costs the most?
- Riddle: Where do you take a sick boat?
- Riddle: Who has a neck and no head, two arms and no hands?
- 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?
- Riddle: What gets bigger the more you take away?
- Riddle: What has ten letters and starts with gas?
- Riddle: How can you drop a raw egg onto a concrete floor without cracking it?
- Riddle: What has a bottom at the top?
- Riddle: Two men are in a desert. They both have backpacks on. One of the guys is dead. The guy who is alive has his backpack open, and the guy who is dead has his backpack closed. What is in the dead man's backpack?
- Riddle: What tastes better than it smells?
- Riddle: What has four fingers and a thumb but isn't alive?
- Riddle: Two fathers and two sons are in a car, yet only three people are in the car. How?
Answer: A fly.
Answer: "Incorrectly."
Answer: Your name.
Answer: A fishhook.
Answer: Blew.
Answer: "Hiss" and "hers."
Answer: A goldfish.
Answer: To the dock-tor.
Answer: A shirt.
Answer: All the passengers are married.
Answer: A hole.
Answer: An automobile.
Answer: Concrete floors are very hard to crack.
Answer: Your legs.
Answer: A parachute.
Answer: Your tongue.
Answer: A glove.
Answer: They are a grandfather, father, and son.
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Tough Riddles About Words and Linguistics
Best Life- Riddle: I belong in December, but not in any other month. I am not a holiday. What am I?
- Riddle: One of these words does not belong: Brawl, Carrot, Change, Clover, Proper, Sacred, Stone, Seventy, Swing, Travel.
- Riddle: White bird, featherless. Flying out of paradise. Flying over sea and land. Dying in my hand. What is it?
- Riddle: What 5-letter word, if typed in all capital letters, can be read the same upside down?
- Riddle: How do you spell COW in thirteen letters?
- Riddle: I'm everywhere and a part of everyone. I am at the end of space and time and existence itself. What am I?
- Riddle: What is seen in the middle of March and April that can't be seen at the beginning or end of either month?
- Riddle: What word in the English language does the following: 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?
- Riddle: What comes once in a minute, twice in a moment, but never in a thousand years?
- Riddle: What is the longest word in the dictionary?
- Riddle: Where is the only place where today comes before yesterday?
- Riddle: How many letters are in the alphabet?
- Riddle: It cannot be seen, cannot be felt, cannot be heard, cannot be smelt. It lies behind stars and under hills and empty holes it fills. It comes first and follows after, ends life, and kills laughter.
- Riddle: With pointed fangs, I sit and wait; with piercing force, I crunch out fate. I grab victims, proclaiming might, and physically join with a single bite. What am I?
- Riddle: If the prisoner tells a lie, he'll be hanged; if he tells the truth, he'll be beheaded. What can he say to save himself?
- Riddle: What English word retains the same pronunciation, even after you take away four of its five letters?
Answer: The letter "D."
Answer: Carrot. It's the only word that does not become another word when you remove the first and last letters.
Answer: A snowflake.
Answer: SWIMS.
Answer: SEE O DOUBLE YOU.
Answer: The letter "E."
Answer: The letter "R."
Answer: Heroine.
Answer: The letter "M."
Answer: "Smiles," because there is a mile between each "s."
Answer: The dictionary.
Answer: There are 11 letters in the words "the alphabet."
Answer: Darkness.
Answer: A stapler.
Answer: "You will hang me."
Answer: "Queue."
This story has been updated to include additional entries, fact-checking, and copy-editing.
