Tricky Riddles That’ll Twist Your Brain
What comes once in a minute, twice in a moment, but never in a thousand years?
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The letter M.
The more you take, the more you leave behind. What am I?
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Footsteps.
A plane crashes on the border of the U.S. and Canada. Where do they bury the survivors?
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Nowhere—survivors aren’t buried.
What word is spelled incorrectly in every dictionary?
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Incorrectly.
You see me once in June, twice in November, but not at all in May. What am I?
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The letter E.
A man dressed in black is walking down a country lane. Suddenly, a large black car with no lights on comes around the corner and screeches to a halt. How did the driver see him?
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It was daytime.
What has a head, a tail, but no body?
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A coin.
You’re in a dark room with a match, a candle, a lamp, and a fireplace. What do you light first?
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The match.
A cowboy rode into town on Friday. He stayed for three nights and left on Friday. How is that possible?
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His horse’s name is Friday.
What five-letter word becomes shorter when you add two letters to it?
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Short.
More Twists and Gotchas
What disappears as soon as you say its name?
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Silence.
If there are three apples and you take away two, how many do you have?
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Two—you took them.
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?
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Four sisters and three brothers.
What can be broken, but never held?
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A promise.
What gets bigger the more you take away from it?
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A hole.
What has many keys but can’t open any doors?
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A piano.
A truck driver is going the wrong way on a one-way street. A police officer sees him but doesn’t stop him. Why?
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He was walking.
What can’t be used until it’s broken?
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An egg.
How many months have 28 days?
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All of them.
If you have me, you want to share me. Once you share me, you no longer have me. What am I?
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A secret.
Classic Stumpers
Before Mount Everest was discovered, what was the highest mountain on Earth?
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Mount Everest—it was just undiscovered.
What can run, but never walks, has a mouth but never talks?
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A river.
Which is heavier: a ton of bricks or a ton of feathers?
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Neither—they both weigh a ton.
A man was born in 1995 and died in 1953. How is that possible?
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He was born in room 1995 and died in room 1953.
A rooster lays an egg on the border between two countries. Who owns the egg?
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No one—roosters don’t lay eggs.
The more you take away from me, the bigger I get. What am I?
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A hole.
You see a boat filled with people, but there isn’t a single person on board. How?
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They’re all married.
FAQ
Are answers included?
Yes. Every riddle includes the answer.
Too hard for kids?
Many work for ages 10 and up. Younger solvers may need a category hint.
Want more hard puzzles?
See hard riddles with answers.