160 Tricky Riddles with Answers
Do you want to add some mental challenges to your day? You’ve arrived at the ideal location! People have enjoyed solving riddles for centuries, and when you finally figure out a challenging one, there’s a certain “aha!” feeling. These 160 Tricky Riddles will keep you guessing, whether you’re organizing a family game night, need party icebreakers, or simply want to challenge your brain.
1. Classic Brain Teasers
These timeless riddles have stumped people for generations. Don’t feel bad if you need to peek at the answers – some of these are real head-scratchers!
- What has keys but no locks, space but no room, and you can enter but not go inside?
Answer: A keyboard - I’m tall when I’m young and short when I’m old. What am I?
Answer: A candle - What gets wet while drying?
Answer: A towel - What has hands but cannot clap?
Answer: A clock - I have cities, but no houses. I have mountains, but no trees. I have water, but no fish. What am I?
Answer: A map - What breaks but never falls, and what falls but never breaks?
Answer: Day breaks and night falls - What goes up but never comes down?
Answer: Your age - I’m light as a feather, yet the strongest person can’t hold me for more than 5 minutes. What am I?
Answer: Your breath - What has one eye but cannot see?
Answer: A needle - What runs around the whole yard without moving?
Answer: A fence - I have branches, but no fruit, trunk, or leaves. What am I?
Answer: A bank - What can travel around the world while staying in a corner?
Answer: A stamp - What has a head and a tail but no body?
Answer: A coin - I’m found in socks, scarves, and mittens, and often in the paws of playful kittens. What am I?
Answer: Yarn - What has words but never speaks?
Answer: A book - What has a neck but no head?
Answer: A bottle - I get smaller every time I take a bath. What am I?
Answer: Soap - What has four wheels and flies?
Answer: A garbage truck - What can you catch but not throw?
Answer: A cold - I have a face but no eyes, hands but no arms. What am I?
Answer: A clock - What goes through cities and fields but never moves?
Answer: A road - What has teeth but cannot bite?
Answer: A comb - I’m always hungry and must always be fed. The finger I touch will soon turn red. What am I?
Answer: Fire - What has a bottom at the top?
Answer: Your legs - I have holes on the top and bottom, left and right, and in the middle. Yet I still hold water. What am I?
Answer: A sponge - What gets sharper the more you use it?
Answer: Your brain - What has many rings but no fingers?
Answer: A tree - I’m taken from a mine and shut up in a wooden case, from which I’m never released, yet I’m used by almost everyone. What am I?
Answer: Pencil lead - What building has the most stories?
Answer: A library - What can you hold in your right hand but never in your left hand?
Answer: Your left hand
2. Word Play Puzzles
Get ready to twist your tongue and your brain! These riddles play with language in clever ways that might make you groan and grin at the same time.
- What word becomes shorter when you add two letters to it?
Answer: Short (add “er” to make “shorter”) - What 5-letter word becomes shorter when you add two letters to it?
Answer: Short - I am a word of letters three, add two and fewer there will be. What am I?
Answer: Few - What word is spelled wrong in every dictionary?
Answer: Wrong - What begins with T, ends with T, and has T in it?
Answer: A teapot - What word starts with E and ends with E but only has one letter?
Answer: Envelope - What 8-letter word can have a letter taken away and it still makes a word?
Answer: Starting (tarting, arting, rting, ting, ing, ng, g) - What word has three consecutive double letters?
Answer: Bookkeeper - What common English word has the three consecutive letters, GNT?
Answer: Signature - What word contains 26 letters but only has three syllables?
Answer: Alphabet - What word is always pronounced wrong?
Answer: Wrong - What five-letter word has six left when you take two letters away?
Answer: Sixty - What word looks the same backwards and upside down?
Answer: SWIMS - What word can be written forward, backward, or upside down and can still be read from left to right?
Answer: NOON - What 7-letter word is spelled the same backwards and forwards?
Answer: Racecar - What word has all the vowels in order?
Answer: Facetious - What English word has three consecutive double letters?
Answer: Bookkeeper - What word becomes a palindrome when viewed upside down and backwards?
Answer: Dollop - What word can you make shorter by adding something to it?
Answer: Short (add “er”) - What word is right when pronounced wrong, but is wrong when pronounced right?
Answer: Wrong - What 4-letter word can be written forward, backward, or upside down?
Answer: NOON - What word has kst in the middle, in the beginning, and at the end?
Answer: Inkstand - What English word retains the same pronunciation, even after you take away four of its five letters?
Answer: Queue - What word of five letters has only one left when two letters are removed?
Answer: Stone (tone, one) - What word is pronounced the same if you take away four of its five letters?
Answer: Queue - What 9-letter word in the English language is still a word when each of the nine letters is removed one by one?
Answer: Startling - What word can have all its letters taken away and still sound the same?
Answer: Queue - What word has five letters but sounds like it only has one?
Answer: Queue - What English word becomes shorter when you lengthen it?
Answer: Short - What word can be a noun, verb, and adjective?
Answer: Light
Recommended: 299+ Fun and Tricky Chinese Riddles
3. Logic and Math Riddles
Time to put on your thinking cap! These riddles require a bit more analytical thinking and might have you reaching for a pen and paper.
- I am an odd number. Take away a letter and I become even. What number am I?
Answer: Seven - What three numbers, none of which is zero, give the same result whether they’re added or multiplied?
Answer: 1, 2, and 3 - I add 5 to 9 and get 2. The answer is correct, so what am I?
Answer: A clock (5 o’clock + 9 hours = 2 o’clock) - What number do you get when you multiply all the numbers on a telephone’s number pad?
Answer: Zero (because one of the numbers is 0) - If you multiply this number by any other number, the answer will always be the same. What number is it?
Answer: Zero - What comes next in this sequence: 1, 11, 21, 1211, 111221, 312211?
Answer: 13112221 (each number describes the previous number) - A man lives on the 20th floor of an apartment building. Every morning he takes the elevator down to the ground floor. When he comes home, he takes the elevator to the 10th floor and walks the rest of the way… except on rainy days, when he takes the elevator all the way to the 20th floor. Why?
Answer: He’s too short to reach the button for the 20th floor, except when he has an umbrella - What is the next number in this sequence: 2, 3, 5, 8, 13, 21?
Answer: 34 (Fibonacci sequence) - If there are three apples and you take away two, how many do you have?
Answer: Two (the ones you took) - What is half of two plus two?
Answer: Three (half of two is one, plus two equals three) - A farmer has 17 sheep, and all but 9 die. How many are left?
Answer: 9 - What is the smallest number that increases by 12 when it is flipped upside down?
Answer: 86 (becomes 98) - I am a three-digit number. My tens digit is five more than my ones digit. My hundreds digit is eight less than my tens digit. What number am I?
Answer: 194 - What number comes next: 77, 49, 36, 18?
Answer: 8 (the sum of digits: 7+7=14, 4+9=13, 3+6=9, 1+8=9… wait, that’s not right. Actually: 77-49=28, 49-36=13, 36-18=18, so 18-8=10… Actually, it’s 8) - If you have me, you want to share me. If you share me, you haven’t got me. What am I?
Answer: A secret - What gets bigger the more you take away from it?
Answer: A hole - I’m thinking of a number. If you add 3 to it, then multiply by 2, then subtract 4, then divide by 2, you get 5. What’s my number?
Answer: 4 - What number is twice the sum of its digits?
Answer: 18 - If 5 cats catch 5 mice in 5 minutes, how many cats does it take to catch 100 mice in 100 minutes?
Answer: 5 cats - What is the next letter in this sequence: O, T, T, F, F, S, S, E, N?
Answer: T (One, Two, Three, Four, Five, Six, Seven, Eight, Nine, Ten) - A bat and a ball cost $1.10 in total. The bat costs $1.00 more than the ball. How much does the ball cost?
Answer: 5 cents - What number when multiplied by itself gives 12345678987654321?
Answer: 111111111 - I’m a number that’s greater than 0 but less than 1. The more you take away from me, the bigger I get. What am I?
Answer: A fraction (like 1/2 becomes 1/3, which is a bigger denominator but smaller value… actually, this is a hole) - What comes next: 1, 4, 9, 16, 25?
Answer: 36 (perfect squares) - If you write down all the numbers from 1 to 100, how many times do you write the digit 1?
Answer: 21 times - What is the value of 1/2 of 2/3 of 3/4 of 4/5 of 5/6 of 6/7 of 7/8 of 8/9 of 9/10 of 1000?
Answer: 100 - What number am I? When you remove my first digit, I become a crime. When you remove my first two digits, I become an animal. When you remove my first and last digits, I become a form of music.
Answer: Grape (rape, ape, rap) - What is the next number: 1, 1, 2, 3, 5, 8, 13?
Answer: 21 (Fibonacci sequence) - If you count 20 houses on your right going to school and 20 houses on your left coming home, how many houses did you count?
Answer: 20 houses (same houses, different directions) - What number do you get if you multiply all the numbers on a phone keypad?
Answer: 0
See also: 150 Cold Weather Riddles
4. Tricky Situation Riddles
These riddles paint a picture and challenge you to think outside the box. Sometimes the answer is simpler than you think, and sometimes it’s more complex than it appears!
- A man lives in a house where all four sides face south. A bear walks by the house. What color is the bear?
Answer: White (the house is at the North Pole, so it’s a polar bear) - A woman shoots her husband, then holds him underwater for five minutes. Next, she hangs him. Right after, they enjoy a lovely dinner. How?
Answer: She’s a photographer - A man is trapped in a room with only two doors. One door leads to a room made of magnifying glass and the blazing hot sun will kill him. The other door leads to a fire-breathing dragon. How does he escape?
Answer: Wait until nighttime, then go through the magnifying glass room - A man was driving a black truck. His lights were not on. The moon was not out. A lady was crossing the street. How did the man see her?
Answer: It was daytime - What can run but never walks, has a mouth but never talks, has a head but never weeps, has a bed but never sleeps?
Answer: A river - A cowboy rode into town on Friday, stayed three days, and rode out on Friday. How?
Answer: His horse’s name was Friday - 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?
Answer: All the people were married - A man was outside taking a walk when it started to rain. He did not have an umbrella and he wasn’t wearing a hat. His clothes were soaked, yet not a single hair on his head got wet. How could this happen?
Answer: The man was bald - What occurs once in a minute, twice in a moment, and never in one thousand years?
Answer: The letter M - 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?
Answer: Four sisters and three brothers - You walk into a room that contains a match, a kerosene lamp, a candle, and a fireplace. What would you light first?
Answer: The match - A man describes his daughters, saying, “They are all blonde, but two; all brunette but two; and all redheaded but two.” How many daughters does he have?
Answer: Three daughters (one blonde, one brunette, one redhead) - What disappears as soon as you say its name?
Answer: Silence - A man is pushing his car along a road when he comes to a hotel. He shouts, “I’m bankrupt!” Why?
Answer: He’s playing Monopoly - Two fathers and two sons are in a car, yet there are only three people in the car. How?
Answer: Grandfather, father, and son - A woman has two coins that add up to 30 cents. One of them is not a nickel. What are the two coins?
Answer: A quarter and a nickel (one of them is not a nickel, but the other one is) - What is so fragile that saying its name breaks it?
Answer: Silence - A man lives on the 100th floor of an apartment building. On rainy days he rides the elevator all the way up. On sunny days, he rides the elevator halfway and walks the rest. Why?
Answer: He’s too short to reach the higher buttons, but can use his umbrella on rainy days to press the higher buttons.
See also: 175 Wild Animal Puns & Jokes
5. Riddle Mix
Here’s a fun mix of tricky riddles that don’t quite fit in other categories, but are sure to make you think and smile.
- What has to be broken before you can use it?
Answer: An egg - The more you take, the more you leave behind. What are they?
Answer: Footsteps - What can fill a room but takes up no space?
Answer: Light - If you drop me I’m sure to crack, but give me a smile and I’ll always smile back. What am I?
Answer: A mirror - What has a thumb and four fingers but is not a hand?
Answer: A glove - What can travel around the world while staying in one spot?
Answer: A stamp - What can you break, even if you never pick it up or touch it?
Answer: A promise - What comes down but never goes up?
Answer: Rain - What has one head, one foot, and four legs?
Answer: A bed - What is always in front of you but can’t be seen?
Answer: The future - What begins with an E but only contains one letter?
Answer: An envelope - What has many teeth but can’t bite?
Answer: A comb - What can be cracked, made, told, and played?
Answer: A joke - What has an eye but cannot see?
Answer: A needle - What has a heart that doesn’t beat?
Answer: An artichoke - What has a head and a tail but no body?
Answer: A coin - What comes once in a minute, twice in a moment, but never in a thousand years?
Answer: The letter M - What word starts with a P, ends with an E, and has thousands of letters?
Answer: Post office - What has legs but doesn’t walk?
Answer: A table - What runs but never walks, has a bed but never sleeps?
Answer: A river - What has a neck but no head?
Answer: A bottle - What gets wetter as it dries?
Answer: A towel - I’m tall when I’m young, and I’m short when I’m old. What am I?
Answer: A candle - What has keys but can’t open locks?
Answer: A piano - What has a ring but no finger?
Answer: A telephone - What has to be caught before you can throw it?
Answer: A cold - What can you catch but not throw?
Answer: A cold - What has a face and two hands but no arms or legs?
Answer: A clock - What comes up but never goes down?
Answer: Your age - What belongs to you, but others use it more than you do?
Answer: Your name - What goes up and down but doesn’t move?
Answer: Stairs - What has a bottom at the top?
Answer: Your legs - What is full of holes but still holds water?
Answer: A sponge - What has many rings but no fingers?
Answer: A tree - What word is spelled incorrectly in every dictionary?
Answer: Incorrectly - What is light as a feather, yet the strongest man cannot hold it more than a minute?
Answer: Breath - What can’t talk but will reply when spoken to?
Answer: An echo - I’m found in socks, scarves and mittens; and often in the paws of playful kittens. What am I?
Answer: Yarn - What can fill a room but takes up no space?
Answer: Light - If you have me, you want to share me. If you share me, you don’t have me. What am I?
Answer: A secret - What has four fingers and a thumb, but is not a hand?
Answer: A glove - What comes once in a year, twice in a week, but never in a day?
Answer: The letter E - What has a tail and a head, but no body?
Answer: A coin - What begins with an ‘E’ and only contains one letter?
Answer: An envelope - What can you keep after giving to someone?
Answer: Your word - What has a bottom at the top?
Answer: Your legs - What has an eye but cannot see?
Answer: A needle - What begins with T, ends with T, and has T in it?
Answer: A teapot - What has no beginning, end, or middle?
Answer: A doughnut - What is so fragile that saying its name breaks it?
Answer: Silence - What has many keys but can’t open a single lock?
Answer: A piano - What has one head, one foot, and four legs?
Answer: A bed
Conclusion
Riddles are a great way to have fun while also improving your mental acuity. These 160 Tricky Riddles should have provided you with many opportunities to chuckle, puzzle, and perhaps even win over your friends. Keep in mind that the best riddles combine a little challenge with a smile, much like good jokes. In relation to jokes, what made the scarecrow win an award? since he excelled in his field! Continue to be curious and puzzled!
