50+ Tricky Riddles (With Answers) to Test Your Smarts [2020]

There is something so fun about a good ol’ riddle. Although an easy riddle is so good for kids, tricky riddles and brain teasers are great for teens and adults looking to elevate their logical thinking skills and cognitive abilities. 

A good riddle is one that really makes you think, one that uses the depths of your brain in search of the answer, one that makes you say, “You know what? I don’t know. What’s the answer?” 

If you’re looking for a fun brain teaser or some hard riddles, then you came to the right place. Here is a collection of some of our favorite riddles! There are some tricky riddles and funny jokes that are great for kids to try and answer, as well as the more challenging riddles

Tricky Yet Fun Riddles

You walk into a room that contains a match, a kerosene lamp, a candle, and a fireplace. What would you light first?

The match. 

How many letters are in the alphabet?

There are 11 letters in “the alphabet”.

Which will burn longer: the candles on the birthday cake of a boy or the candles on the birthday cake of a girl?

No candles burn longer–they all burn shorter. 

What five-letter word stays the same when you take away the first, third, and last letter?


A man is asked what his daughters look like. He answers, “they are all blondes, but two, all brunettes, but two, and all redheads, but two.” How many daughters does he have?

Three. One is blonde, one is brunette, and one is a redhead.

Two in a corner, 1 in a room, 0 in a house, but 1 in a shelter. What am I?

The letter “R”

What English word does the following: the first two letters signify a male, the first three letters signify a female, the first four letters signify a great person, while the entire word signifies a great woman. What is the word?


A plane crashed between the border of Canada and America. Where do you bury the survivors?

They are survivors, you don’t bury them.

Which word in the dictionary is always spelled incorrectly?


What word is pronounced the same if you take away four of its five letters?


If there are three cups of sugar and you take one away, how many do you have?

One cup of sugar. 

In a bus, there is a 26-year-old pregnant lady, a 30-year-old policeman, a 52-year-old random woman, and the driver who is 65 years old. Who is the youngest?

The baby of the pregnant lady.

David’s father has three sons: Snap, Crackle and…? 


What has thirteen hearts but no other organs?

A deck of cards.

A boy and an engineer were fishing. The boy is the son of the engineer but the engineer is the father of the boy. Then who is the engineer?

The engineer is the boy’s mother. 

What is something you can keep after giving to someone?

Your word.

Soldiers line up, spaced with pride, two long rows lined side by side, one sole unit can decide if the rows will unite or divide. What is it?

A zip. 

What occurs once in a minute, twice in a moment, and never in one thousand years?

The letter “M”

What is so fragile that saying its name breaks it?


I occur twice in eternity, and I’m always within sight. What am I?

The letter “T” 

When I am alive I do not speak. Anyone who wants to takes me captive and cuts off my head. They bite my bare body. I do no harm to anyone unless they cut me first. Then I soon make them cry. What am I?

An onion.

You always find me in the past, I can be created in the present, but the future can never taint me. What am I?


How can you drop a raw egg on the concrete floor without cracking it?

The egg won’t crack the concrete floor! 

All 5 sisters are busy. Ann is reading a book, Rose is cooking, Katy is playing chess, and Mary is doing the laundry. What is the 5th sister doing?

She’s playing chess, of course! 

A monkey, a squirrel, and a bird are racing to the top of a coconut tree. Who gets to the banana first” the monkey, the squirrel, or the bird?

There are no bananas at the top of a coconut tree!

Bonus Riddle:

Here’s a clever riddle to really make you think. 

A man was found murdered on Sunday morning. His wife immediately called the police. The police went to the crime scene and question the wife and staff and got these alibis: The wife said she was sleeping, the cook was eating breakfast, the gardener was picking vegetables, the maid was getting the mail, the butler was cleaning the closet. The police instantly arrested the murderer. Who did it and how did they know?

It was the Maid. She said she was getting the mail but there’s no mail on Sundays!

Hard Riddles

Two girls were born to the same mother, on the same day, at the same time, in the same month and year, and yet they’re not twins. How can this be?

The two babies are two of a set of triplets.

Three doctors said that Robert is their brother. Robert says he has no brothers. Who’s lying?

No one is lying – Robert has 3 sisters who all happen to be doctors. 

We hurt without moving and poison without touching. We bear truth and lies but are not judged by size. What are we?


Which English word is the odd one out – Stun, Ton, Evil, Letter, Mood, Bad, Snap, Straw?


What English word has three consecutive double letters?


Poor people have it. Rich people need it. If you eat it you die. What is it?


A man is found murdered in his office. The suspects are Peter, Julie, Jason, Molly, and Brian. In the office is a calendar with the numbers 6,4,9,10,11 written in blood. Who is the killer?

Jason is the killer. The numbers indicate months and the first letter of each month spells the name of the murderer, e.g. the 6th month is June and the first letter of June is J, the 4th month is April and the first letter of April is a, and so on.

Two fathers and two sons are in a car, yet there are only three people in the car. How?

They are a grandfather, father, and son.

The person who makes it has no need of it; the person who buys it has no use for it. The person who uses it can neither see nor feel it. What is it?

A coffin 

A woman shoots her husband, then holds him underwater for five minutes. Next, she hangs him. Right after, they enjoy a lovely dinner. Explain.

She took a picture of him and developed it in her darkroom.

A man is trapped in a room. The room has only two possible exits: two doors. Through the first door, there is a room constructed from magnifying glasses. The blazing hot sun instantly fries anything or anyone that enters. Through the second door, there is a fire-breathing dragon. How does the man escape?

He waits until night time and then goes through the first door.

What can go up a chimney down, but can’t go down a chimney up?

An umbrella.

My first is in chocolate but not in ham, my second’s in cake and also in jam, my third at tea-time is easily found, my whole is a friend who’s often around. What am I?

A cat.

A murderer is condemned to death. He has to choose between three rooms: the first is full of raging fires; the second, assassins with loaded guns, and the third, with lions who haven’t eaten in years. Which room is the safest?

The room with the lions because the lions are already dead. 

A woman is sitting in her hotel room when there is a knock at the door. She opened the door to see a man whom she had never seen before. He said, “Oh I’m sorry. I have made a mistake. I thought this was my room.” He then went down the corridor and in the elevator. The woman went back into her room and phoned security. What made the woman so suspicious of this man?

You don’t knock on your own hotel room door! 

Bonus Riddle

Here’s a brain teaser that honestly might hurt the brain trying to figure out the answer… 

My buddies and I were inseparable mates
Til one by one were we split
My teacher, she gave me a smack on the pate
And off in the corner I sit.
Admittedly still I’m not hitting the books
Though now I’m hugging a tree
I guess in the end it’s not bad as it looks
I went from a C to a B…

(Clue: it’s an object)

A staple

Math Riddles

Math riddles are some of the most difficult riddles to exist. With word problems, numbers, integers, and all the confusing rules of finding the right answer, there’s truly nothing enjoyable about the subject. If you’re a teacher hoping to help your students or you’re just an adult looking to elevate your critical thinking skills and problem-solving abilities, you might enjoy a math puzzle, like one of these below: 

I have two coins equaling fifteen cents. One of them is not a nickel. What are the two coins?

A dime and a nickel. One of the coins is not a nickel, but the other one is. 

If you multiply me by any other number, the answer will always remain the same. What number am I?

The combined age of a father and son is 66 years. The age of the father is the age of the son, but with the digits reversed. How old are they?

51 and 15 or 42 and 24 or 60 and 6. 

A man is found hanging dead from the ceiling of a room. The room’s dimensions are 15 x 15 x 15. The man is only 6ft tall and the rope was only 2ft long. There are no windows and only one door into the room. The door is bolted shut from the inside and there is a puddle of water under the man. How did he kill himself?

The man stood on a block of ice.

Which is correct: 18 plus 19 is 36. Or 18 plus 19 are 36?

Actually, both are incorrect – 18 plus 19 is 37!

When does 11+3=2?

On a clock.

What is special about the number 854,917,632?

It’s the numbers from 1-9 in alphabetical order.

Mom and dad have four daughters, and each daughter has one brother. How many people are in the family?


If you’re 8 feet away from a door and with each move you advance half the distance to the door. How many moves will it take to reach the door? 

You will never reach the door, it will always be half the distance, no matter how small!.

Joe has ten coins totaling $1.19. From these coins, he cannot make exact change for a dollar, half-dollar, quarter, dime, or nickel. What are the coins?

A half-dollar, a quarter, four dimes, and four pennies.

Here’s a fun and somewhat inappropriate math joke — not suitable for kids — to end on a light note: 

What do love and math have in common?

If you add wine, plus a bed, minus the clothes, divide the legs, then you hope and pray you don’t multiply. 

Now, if you’re up for a challenge, here is Albert Einstein’s riddle, a puzzle that is believed to be developed when he was young. The best way to solve this brainteaser is through logic and deductive reasoning. 

Five houses painted five different colors stand in a row. One person of a different nationality lives in each house. The five homeowners all drink some type of beverage, smoke a certain cigar brand, and have a certain kind of pet. But none of the owners drink the same beverage, smoke the same type of cigar, or have the same pet.

Here are the clues:

  1. The Brit lives in the red house.
    2. The Swede keeps dogs as pets.
    3. The Dane drinks tea.
    4. The green house is on the immediate left of the white house.
    5. The green house’s owner drinks coffee.
    6. The owner who smokes Pall Mall rears birds.
    7. The owner of the yellow house smokes Dunhill.
    8. The owner living in the center house drinks milk.
    9. The Norwegian lives in the first house.
    10. The owner who smokes Blends lives next to the one who keeps cats.
    11. The owner who keeps the horse lives next to the one who smokes Dunhill.
    12. The owner who smokes Bluemasters drinks beer.
    13. The German smokes Prince.
    14. The Norwegian lives next to the blue house.
    15. The owner who smokes Blends lives next to the one who drinks water.

Now, the question is…Who owns the fish?

The German in house #4 owns the fish.

What are some of your favorite riddles?

More Riddles

About the author
January Nelson is a writer, editor, dreamer, and occasional exotic dancer and a collective pen name. Read more articles from January on Thought Catalog.

Learn more about Thought Catalog and our writers on our about page.