Hard Riddles With Answers
Updated · Best Riddles With Answers editorial team
Quick answer: These 42 hard riddles with answers are for people who have outgrown the easy ones. Each is hard because of the thinking it needs, not because it is vague, and every answer explains the trick. Begin with the warm-ups, work through the main set, and try the toughest ten without peeking.
Warm-Up Hard Riddles
I fly without wings and cry without eyes. Wherever I go, darkness follows. What am I?
A cloud.
Forward I am heavy, but backward I am not. What am I?
Ton (backward it spells not).
What five-letter word becomes shorter when you add two letters to it?
Short, which becomes shorter.
I have a head and a tail but no body. What am I?
A coin.
What is always in front of you but can never be seen?
The future.
What word is spelled incorrectly in every dictionary?
Incorrectly.
What can fill an entire room and take up no space at all?
Light.
What breaks without ever falling, and what falls without ever breaking?
Day breaks and night falls.
What invention lets you see right through a wall?
A window.
What goes up and down all day but never moves?
Stairs.
I am always hungry and must be fed, and the finger I touch soon turns red. What am I?
Fire.
What can you break even if you never pick it up or touch it?
A promise.
Main Set Hard Riddles
What can be seen in the middle of March and April that cannot be seen at the beginning or end of either month?
The letter R.
Written in capital letters, which four-letter word reads the same forward, backward and upside down?
Noon.
What English word has three pairs of double letters in a row?
Bookkeeper.
Spelled out, which number from one to one hundred has its letters in perfect alphabetical order?
Forty (F, O, R, T, Y).
A rooster lays an egg on the very peak of a roof. Which way does the egg roll?
Neither way, because roosters do not lay eggs.
I begin with P and end with E, and I have thousands of letters. What am I?
The post office.
A man shaves several times a day, yet he still has a beard. Who is he?
A barber.
What walks on four legs in the morning, two at noon and three in the evening?
A human being, who crawls as a baby, walks upright, and uses a stick in old age.
I have branches but no trunk, no leaves and no fruit. What am I?
A bank.
Which English word means both to stick together and to split apart?
Cleave.
You throw me out when you want to use me, and you haul me back in when you are finished. What am I?
An anchor.
The poor have it, the rich need it, and if you eat it you will die. What is it?
Nothing.
Toughest Hard Riddles
What letter comes next: J, F, M, A, M, J, J, A, S?
O. The letters begin the months, so October follows September.
Which two-word phrase is an anagram of the word dormitory?
Dirty room.
What contains 26 letters, yet has only three syllables?
The alphabet.
The day before yesterday I was 25, and next year I will be 28. How is this possible?
It is January 1 and my birthday is December 31. I was 25 on December 30, turned 26 the next day, turn 27 this December and 28 the year after.
What is the longest word in the English language?
Smiles, because there is a mile between the first and last letters.
If two is company and three is a crowd, what are four and five?
Nine.
What word do even the best speakers get wrong, whatever they say?
Wrong.
A clerk is asked how many seconds there are in a year. She says twelve. Why?
There is a second of every month: January 2, February 2 and so on, twelve in all.
What has a spine, many leaves and tells a story without speaking?
A book.
Quick-Fire Hard Riddles
What must be broken before you can use it?
An egg.
What flies without wings and never stops?
Time.
What has a bark but no bite?
A tree.
What is black when clean and white when dirty?
A blackboard.
What has no beginning, no end and no middle?
A circle.
What kind of coat is always put on wet?
A coat of paint.
What grows up while it grows down?
A goose, which grows up and has goose down on it.
What is the beginning of the end and the end of time and space?
The letter E.
How to Tackle Hard Riddles
Most hard riddles hide their trick in one ordinary word. Read the question slowly and ask which word could mean something else. Words such as break, fall, right and coat often carry two meanings, and the answer appears as soon as you pick the second one.
If you are stuck, say the riddle aloud, write the letters down, or test your guess against every clue. Walk away and return later, because a fresh mind often finds the answer in seconds. Finally, read the explanation after each answer so the trick works for you next time.
Frequently Asked Questions
What makes a riddle hard?
A hard riddle hides its meaning behind a double meaning, a trap or an unusual way of thinking. The clues are fair, but you have to question a word you took for granted.
How can I get better at solving hard riddles?
Practise regularly, read the explanation of every answer, and notice recurring tricks such as double meanings, letter play and hidden assumptions. Over time you start to spot these patterns quickly.
Are there hard riddles with no clear answer?
A good riddle always has a fair answer that fits every clue. Every riddle on this page has one, and each explanation shows the reasoning so you can check it yourself.
Which hard riddles should I try first?
Start with the warm-ups, where the trick is a single word. Then move to the main set, which includes letter and number tricks, and save the toughest ten for when you feel confident.
