27 Tricky Riddles with Answers That’ll Outsmart You
These aren’t your average riddles.
Each one of these 27 tricky riddles has a twist—and they’re meant to outsmart you on the first try. But once the answer clicks, you’ll realize how obvious (and clever) they really are.
Perfect for riddle fans, trivia nights, puzzle nerds, and anyone who loves a mental challenge.
Tricky Riddles That’ll Twist Your Brain 🌀
What comes once in a minute, twice in a moment, but never in a thousand years?
The more you take, the more you leave behind. What am I?
A plane crashes on the border of the U.S. and Canada. Where do they bury the survivors?
What word is spelled incorrectly in every dictionary?
You see me once in June, twice in November, but not at all in May. What am I?
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?
What has a head, a tail, but no body?
You’re in a dark room with a match, a candle, a lamp, and a fireplace. What do you light first?
A cowboy rode into town on Friday. He stayed for three nights and left on Friday. How is that possible?
What five-letter word becomes shorter when you add two letters to it?
What disappears as soon as you say its name?
If there are three apples and you take away two, how many do you have?
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?
What can be broken, but never held?
What gets bigger the more you take away from it?
What has many keys but can’t open any doors?
A truck driver is going the wrong way on a one-way street. A police officer sees him but doesn’t stop him. Why?
What can’t be used until it’s broken?
How many months have 28 days?
If you have me, you want to share me. Once you share me, you no longer have me. What am I?
Before Mount Everest was discovered, what was the highest mountain on Earth?
What can run, but never walks, has a mouth but never talks?
Which is heavier: a ton of bricks or a ton of feathers?
A man was born in 1995 and died in 1953. How is that possible?
A rooster lays an egg on the border between two countries. Who owns the egg?
The more you take away, the stronger I get. What am I?
You see a boat filled with people, but there isn’t a single person on board. How?
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