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120 Really Tricky Riddles To Test Your Wits
CuriositiesMAR 9, 2023

120 Really Tricky Riddles To Test Your Wits

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So you think you’re a pro at solving brainteasers, and no tricky riddles baffle you?
Well then, we’re a bit jealous because that means your critical thinking abilities are among the likes of Sherlock Holmes and Hercule Poirot. However, if you’d like to really test your problem-solving prowess, we’ve made a list full of very tricky riddles – have a go at them!
But before you do, have you ever wondered what these hard riddles really are? Well, it turns out these brainbusters are classified as verbal puzzles with double or veiled meanings.
Moreover, everyone’s beloved fun riddles can be divided into two types: enigmas (yeah, like that ’90s band!), which are problems expressed in metaphorical or allegorical language, and conundra, which are questions relying on puns (either in the question or in the answer).
Now, it’s up to you to decide which type of brainteaser you like better, but we think that enigmas do make really tricky riddles.
And lastly, before we skip to our selection of short tricky riddles with answers, you might find it amusing to know that the oldest known riddles come from the Babylonian times!
It turns out that we have loved tricking each other and picking our brains since the dawn of civilization (if not earlier, who knows!). 
Right, with all the introductions done, it’s probably the time to start solving! Our picks of the most awesome tricky riddles with answers are just a bit further down, and once you are there, be sure to give the riddles that stumped you your vote.
After that, share this article with your friends and see how they do with these tricky riddles. 

#1

A woman is sitting in her hotel room when someone knocks at the door. She opened the door to find a man she’s never seen before. He says, “Oh I’m sorry, I made a mistake and thought this was my room.” He then ran away and got into an elevator so the woman shut her door and phoned security. What made the woman so suspicious?
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56points

#2

120 Really Tricky Riddles To Test Your Wits
Three different doctors said that Paul is their brother yet Paul claims he has no brothers. Who is lying?
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49points

#3

What comes once in a minute, twice in a moment, but never in a thousand years?
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45points

#4

A murderer is condemned to death and he has the option to die in one of the following three rooms: a room full of raging fire, a room full of assassins with loaded guns, and a room full of lions who haven’t eaten in years. Which room should he choose?
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41points

#5

120 Really Tricky Riddles To Test Your Wits
What English word has three consecutive double letters?
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40points

#6

What is full of holes but still holds a lot of water?
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40points

#7

You measure my life in hours and I serve you by expiring. I’m quick when I’m thin and slow when I’m fat. The wind is my enemy.
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31points

#8

What is seen in the middle of March and April that can’t be seen at the beginning or end of either month?
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29points

#9

Which English word is the odd one out: Stun, Ton, Evil, Letter, Mood, Bad, Strap, Snap, and Straw?
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27points

#10

120 Really Tricky Riddles To Test Your Wits
What gets wet while drying?
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26points

#11

Why is Europe like a frying pan?
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26points

#12

How can you physically stand behind your father while he is standing behind you?
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25points

#13

What falls but never breaks? What breaks but never falls?
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25points

#14

Two fathers and two sons come home from the mall. Yet when they arrive home, only three people get out of the car. How is this possible?
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24points

#15

120 Really Tricky Riddles To Test Your Wits
When I am needed by you, you throw me away, but when I’m of no use, you take me back. What am I?
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24points

#16

Humans purchase me to eat but then never eat me. What am I?
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24points

#17

What word starts with E and ends with E but only has one letter?
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23points

#18

I fly without wings and cry without eyes. Wherever I lead, darkness follows. What could I be?
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23points

#19

Where can you finish a book without finishing a sentence?
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23points

#20

120 Really Tricky Riddles To Test Your Wits
What’s unique about this number: 854, 917, 632?
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22points
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