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
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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
Conclusion
If you made it through all 150+ riddles and still have your sanity intact, well done, you’ve got one seriously nimble mind.
Or at least a stubborn streak strong enough to resist the urge to scroll down for answers too quickly (no judgment if you did).
I hope these riddles gave you something more than just answers.
Maybe a laugh. Maybe a pause.
Maybe a quiet moment where everything else melted away and all that existed was the question: what on earth is this talking about?
Keep them handy. Share them. Stump your smartest friends.
Or better yet, see how many of them you can remember the next time someone says, “Hit me with a good one.” You’ve got 150+ ready to go.
And if your brain hurts a little… welcome to the club.