The Hardest Riddles

Riddle: Say what?

I speak without a mouth and hear without ears. I have nobody, but I come alive with the wind. What am I? 

This riddle relies on tricking you into thinking about ears and a mouth. You get a tiny hint about wind to encourage you to think broadly and avoid the literal.

Answer: An echo

Riddle: Match game

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. 

Hard riddles want to trip you up, and this one works by hitting you with details from every angle. The big hint comes at the end with the wind. What does wind threaten most? You have to stretch your brain to come up with something tiny and unexpected.

Answer: A candle.

Riddle: Hidden treasure

I have cities, but no houses. I have mountains, but no trees. I have water, but no fish. What am I? 

This riddle aims to confuse you and get you to focus on the things that are missing: the houses, trees, and fish. You might guess you need to think about something inanimate.

Answer: A map

Riddle: Spring ahead

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

This riddle works by trying to get you to think about the weather or holidays or other events linked to a calendar. To get this one right you actually need to get super literal.

Answer: The letter “R.” 

Riddle: Cruising along

You see a boat filled with people. It has not sunk, but when you look again you don’t see a single person on the boat. Why?

Hard riddles like this brainteaser are tricky because they seem to invite straightforward, logical thinking. You may come up with answers like “they all went below deck” or “jumped overboard.” But you need to focus on the word “single” and think about its other meanings.

Answer: All the people were married.

Riddle: Wordplay

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

This is hard because it gets you thinking about gender and the ways they’re different. You have to think of one word that holds the others. It’s easy when you think about it!

Answer: Heroine

Riddle: Good with numbers

What English word has three consecutive double letters? 

This one is pretty impossible but use the facts you know about English to get on track. First, think of words with double vowels. And you must know this is probably going to be a compound word. The first and last letters of those combined words will form one set of double letters. Now, just wrack your brain!

Answer: Bookkeeper.

Riddle: Violent delights

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

This puzzle aims to throw you off balance with shock. But pay attention to the first verb, “shoots.” What else can you shoot with besides a gun? There lies the key to the whole thing.

Answer: She took a picture of him and developed it in her dark room. 

Riddle: The write stuff

I come from a mine and get surrounded by wood always. Everyone uses me. What am I? 

The idea of a mine might lead you to coal or a diamond. The wood detail is your best hint. This riddle is a toughie, but wood might lead you to figure it out.

Answer: Pencil lead

Riddle: Sibling squad

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 in the family? 

This trick question gives you a bunch of ways to get totally confused if you try to figure out the answer. The key is to keep it simple. Be sure to count the sisters and brothers in total and in terms of their own number of siblings. Then the answer gets a little easier.

Answer: Four sisters and three brothers.

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