150+ Confusing Riddles that bent my mind

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I’ve always been fascinated by riddles, the kind that make your brain ache a little, your eyes squint, and your coffee go cold as you obsess over the answer.

So I decided to go all in and gather some of the most confusing riddles I could find.

Not the “what has four legs” kind of easy stuff, but the kind of riddles that make even adults pause mid-scroll and wonder if their logic circuits need a reboot.

Some of these will trip you up with wordplay. Others will wrap your thoughts in knots. A few might even make you groan once you read the answer (my favorite kind).

I’ve tested most of them on friends and family and let’s just say not everyone was ready. But that’s the fun of it.

So if you love riddles that twist your brain into pretzels, you’re in the right place. Take a deep breath, trust your gut, and prepare to overthink everything. Let’s get puzzling.

150+ Confusing Riddles that bent my mind

The more you take, the more you leave behind. What am I?
Answer: Footsteps
I speak without a mouth and hear without ears. I have no body, but I come alive with wind. What am I?
Answer: An echo
A man who was outside in the rain without an umbrella or hat didn’t get a single hair on his head wet. Why?
Answer: He was bald
What comes once in a minute, twice in a moment, but never in a thousand years?
Answer: The letter “M”
Forward I am heavy, but backward I am not. What am I?
Answer: The word “ton”
What is always in front of you but can’t be seen?
Answer: The future
What can fill a room but takes up no space?
Answer: Light
The more you take away, the bigger I become. What am I?
Answer: A hole
What has keys but can’t open locks?
Answer: A piano
What can travel around the world while staying in the same corner?
Answer: A stamp
I am not alive, but I grow. I don’t have lungs, but I need air. What am I?
Answer: Fire
What disappears as soon as you say its name?
Answer: Silence
The more there is, the less you see. What is it?
Answer: Darkness
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: 4 sisters and 3 brothers
What comes at the end of everything?
Answer: The letter “g”
You see a boat filled with people. It hasn’t sunk, but when you look again, you don’t see a single person. Why?
Answer: All the people were married
A cowboy rode into town on Friday. He stayed three days and left on Friday. How is this possible?
Answer: His horse’s name is Friday
What flies without wings and cries without eyes?
Answer: A cloud
What has a head, a tail, is brown, and has no legs?
Answer: A penny
What comes down but never goes up?
Answer: Rain
What has many teeth but can’t bite?
Answer: A comb
What is always running but never moves?
Answer: Time
What can be broken but never held?
Answer: A promise
What has hands but can’t clap?
Answer: A clock
What begins with T, ends with T, and has T in it?
Answer: A teapot
What gets wetter the more it dries?
Answer: A towel
You see me once in June, twice in November, but not at all in May. What am I?
Answer: The letter “e”
If two’s company and three’s a crowd, what are four and five?
Answer: Nine
What word is spelled incorrectly in every dictionary?
Answer: Incorrectly
What begins with an E, ends with an E, but only contains one letter?
Answer: An envelope
What invention lets you look right through a wall?
Answer: A window
What has one eye but can’t see?
Answer: A needle
I go in hard, come out soft, and am never the same. What am I?
Answer: Chewing gum
You answer me, although I never ask you questions. What am I?
Answer: A telephone
What can run but never walks, has a bed but never sleeps, and has a mouth but never talks?
Answer: A river
The more of me there is, the less you see. What am I?
Answer: Fog
What has legs but doesn’t walk?
Answer: A table
What can you hold in your left hand but not in your right?
Answer: Your right elbow
What can’t talk but will reply when spoken to?
Answer: An echo
What kind of coat is best put on wet?
Answer: A coat of paint
What belongs to you but other people use it more than you do?
Answer: Your name
If a plane crashes on the border between the US and Canada, where do they bury the survivors?
Answer: Nowhere, because survivors aren’t buried
I shave every day, but my beard stays the same. Who am I?
Answer: A barber
What begins with a P, ends with an E, and has thousands of letters?
Answer: The post office
What kind of tree can you carry in your hand?
Answer: A palm
What can be cracked, made, told, and played?
Answer: A joke
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 comes once in a year, twice in a month, four times in a week, and six times in a day?
Answer: The letter “e”
What begins with an “I” and can help you see?
Answer: An eye
What goes up and down without moving?
Answer: A staircase
What has cities, but no houses; forests, but no trees; and rivers, but no water?
Answer: A map
What has a neck but no head?
Answer: A bottle
What can be touched but can’t be seen?
Answer: Someone’s heart or emotion
What has four fingers and a thumb but isn’t alive?
Answer: A glove
What can you keep after giving it to someone?
Answer: Your word
What type of building has the most stories?
Answer: A library
What has a bottom at the top?
Answer: Your legs
What is so fragile that saying its name breaks it?
Answer: Silence
What word has three consecutive double letters?
Answer: Bookkeeper
What kind of band never plays music?
Answer: A rubber band
What’s easy to lift but hard to throw?
Answer: A feather
What can go up a chimney down, but not down a chimney up?
Answer: An umbrella
What’s full of holes but still holds water?
Answer: A sponge
What begins and has no end, and ends all that begins?
Answer: Death
What runs around the house but doesn’t move?
Answer: A fence
I have branches, but no fruit, trunk, or leaves. What am I?
Answer: A bank
What flies forever, rests never?
Answer: Time
What has no beginning, middle, or end?
Answer: A circle
What word starts and ends with an “e” but only contains one letter?
Answer: Envelope
The more you take, the more I grow. What am I?
Answer: A debt
What has one head, one foot, and four legs?
Answer: A bed
What travels faster: hot or cold?
Answer: Hot, because you can catch cold
What’s something you can’t give someone without keeping it yourself?
Answer: Your word or a promise
What is always coming but never arrives?
Answer: Tomorrow
What gets sharper the more you use it?
Answer: Your brain
What gets bigger the more you take away from it?
Answer: A hole
If you’re running in a race and pass the person in second place, what place are you in?
Answer: Second place
What has a heart that doesn’t beat?
Answer: An artichoke
What can you catch but not throw?
Answer: A cold
What’s always in the middle of nowhere?
Answer: The letter “h”
What occurs once in every minute, twice in every moment, but never in a thousand years?
Answer: The letter “m”
What can one not keep, two hold tight, and three tear apart?
Answer: A secret
What can be heard and caught but never seen?
Answer: A remark or a cold
The person who makes it doesn’t use it. The person who buys it doesn’t want it. The person who uses it doesn’t know it. What is it?
Answer: A coffin
What can you see once in a year, twice in a week, and never in a day?
Answer: The letter “e”
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
What’s greater than God, more evil than the devil, the poor have it, the rich need it, and if you eat it you’ll die?
Answer: Nothing
A word I know, six letters it contains, remove one letter and twelve remains. What is it?
Answer: Dozens
Which is heavier: a pound of feathers or a pound of bricks?
Answer: Neither, they weigh the same
Before Mount Everest was discovered, what was the highest mountain in the world?
Answer: Mount Everest
What’s so delicate that even saying its name breaks it?
Answer: Silence
A box without hinges, key, or lid, yet inside golden treasure is hid. What am I?
Answer: An egg
What has four wheels and flies?
Answer: A garbage truck
What’s the one question you can never answer yes to truthfully?
Answer: Are you asleep?
What has a beginning, a middle, and an end, but no content?
Answer: An empty book or story structure
What question can you never truthfully answer “yes” to?
Answer: Are you dead?
What gets broken without being touched?
Answer: A heart
What word starts with “e,” ends with “e,” and has one letter in it?
Answer: Envelope
What do you throw out when you want to use it and take in when you don’t want to use it?
Answer: An anchor
What is as light as a feather, yet the strongest person can’t hold it for more than a minute?
Answer: Your breath
What comes in the morning without being called, and is lost in the night without being stolen?
Answer: The sun
What has eyes but can’t see?
Answer: A potato
What five-letter word becomes shorter when you add two letters to it?
Answer: Short
I am the beginning of everything, the end of time and space, the beginning of every end and the end of every place. What am I?
Answer: The letter “e”
You can serve it but never eat it. What is it?
Answer: A tennis ball
The more you have of me, the less you see. What am I?
Answer: Darkness
What doesn’t have lungs but needs air?
Answer: Fire
What runs but never gets tired?
Answer: A refrigerator or a clock
What comes once in a second, twice in a decade, but never in a century?
Answer: The letter “e”
A man stands on one side of a river, his dog on the other. He calls the dog, who immediately crosses without getting wet or using a bridge or boat. How?
Answer: The river is frozen
I’m tall when I’m young and short when I’m old. What am I?
Answer: A candle
What has no bones but can break your heart?
Answer: A promise
What can’t be used until it’s broken?
Answer: An egg
You walk into a room with a match, a kerosene lamp, a candle, and a fireplace. Which do you light first?
Answer: The match
The more you take from me, the stronger I become. What am I?
Answer: A black hole or debt
If you have it, you want to share it. If you share it, you no longer have it. What is it?
Answer: A secret
I am always hungry, I must always be fed. The finger I touch, will soon turn red. What am I?
Answer: Fire
What comes in pairs but you use one at a time?
Answer: Eyelids or gloves
What gets sharper the more you use it but dulls when unused?
Answer: Your mind
What begins with a question and ends with confusion?
Answer: A riddle
What’s tall during the day but disappears at night?
Answer: A shadow
What is the longest word in the dictionary?
Answer: Smiles (because there’s a mile between the first and last letters)
What turns everything around without moving?
Answer: A mirror
What has four wheels and no engine?
Answer: A shopping cart
What comes in with two legs but leaves with four?
Answer: A person carrying a chair
What is seen in the middle of March and April that can’t be seen at the beginning or end of either month?
Answer: The letter “r”
What can bring back the dead, make us cry, make us laugh, make us young, is born in an instant, yet lasts a lifetime?
Answer: A memory
What is never used unless it is broken?
Answer: A record or a secret
If you throw a red stone into the blue sea, what will it become?
Answer: Wet
What cannot be seen, cannot be felt, cannot be heard, and cannot be smelt?
Answer: The dark
What comes but never arrives, is waited on by all, and leaves everything behind?
Answer: Tomorrow
What can’t be seen, only described, and disappears when noticed?
Answer: A thought
What changes when you name it?
Answer: A riddle
The person who makes it sells it. The person who buys it never uses it. The person who uses it doesn’t know they are. What is it?
Answer: A coffin
What has 13 hearts but no organs?
Answer: A deck of cards
What’s at the end of the rainbow?
Answer: The letter “w”
What comes in through your eyes but leaves through your mouth?
Answer: Knowledge
What is always around you but hard to see?
Answer: Air
What runs but never has legs, murmurs but never speaks, and dies in silence?
Answer: A stream
What must be broken to be helpful?
Answer: A horse or a habit
What belongs to you but is used more by others?
Answer: Your name
You can’t see me, but I’m there. You can’t touch me, but I affect you. I make you warm, then cold. What am I?
Answer: The wind
What’s the end of everything?
Answer: The letter “g”
What gets bigger the more you share it?
Answer: Joy
What can never be stolen, only given away, and once lost, is hard to get back?
Answer: Trust
What becomes shorter as you use it?
Answer: A pencil
What exists only when you believe in it?
Answer: Faith or imagination
What keeps going up but never comes down?
Answer: Your age
What kind of cup can’t hold water?
Answer: A hiccup
What flies when you’re having fun and crawls when you’re bored?
Answer: Time