When you need a vigorous, sweat-inducing brain workout, attempting to solve some hard riddles is a sure way to get those intellectual reps in. Putting your smarts to the test in this way is not for the faint of heart — or rather, brain — so don’t be discouraged if you get stumped.
Humans have been testing their critical thinking skills with lateral thinking and logic puzzles since ancient times (even further back than the Regency era-inspired charades game in Bridgerton Season 3, Episode 5). The purpose is partly entertainment, but partly for training the brain to think more expansively and creatively.
Riddles are strategically and enigmatically written to ensnare those who attempt them in the weeds of language and interpretation. Approaching a difficult riddle from all angles and filtering out extraneous details is a tried-and-true way to boost your brain health and keep your mind sharp.
Bridgerton is far from the first example of riddles in storytelling. No, it’s well documented that literature from ancient history through the modern era is positively *riddled* (get it?) with complex word puzzles for the main characters to solve. From literature, to pop culture, to history, these are some certified head-scratchers.
The oldest known written riddles date back about 4,000 years to the ancient Sumerians, written in Cuneiform. One of these riddles is about a house that one enters blind and comes out seeing. What is the house? If you guessed a school, you would be as adept and knowledge-oriented as the Sumerians. If not, don’t sweat it, there are plenty more hard riddles to take a crack at here.
Below, find riddle questions followed by their answers.
Hardest Famous Riddles: Questions
- Which is the creature that has one voice, but goes on four legs in the morning, on two legs at noon, and on three legs in the evening? (Oedipus Rex, Sophocles)
- My first displays the wealth and pomp of kings, / Lords of the earth! / their luxury and ease. / Another view of man, my second brings, / Behold him there, the monarch of the seas! (Emma, Jane Austen)
- As I was going to St. Ives, / I met a man with seven wives, / Each wife had seven sacks / Each sack had seven cats / Each cat had seven kits / Kits, cats, sacks, and wives / How many were there going to St. Ives?
- This thing all things devours / Birds, beasts, trees, flowers / Gnaws iron, bites steel / Grinds hard stones to meal / Slays king, ruins town / And beats mountain down. (The Hobbit, J.R.R. Tolkien)
- There are five houses in a row. Each house is painted a different color and has a person of a different nationality living in it. Each person drinks a different beverage, smokes a different type of cigar, and owns a different animal as a pet. Using these 15 clues, which person owns the pet fish?
- The Brit lives in the red house.
- The Swede has a pet dog.
- The Dane drinks tea.
- The green house is directly to the left of the white house.
- The person in the green house drinks coffee.
- The person who smokes Pall Mall has a pet bird.
- The person in the yellow house smokes Dunhill cigars.
- The person in the center house drinks milk.
- The Norwegian lives in the first house.
- The person who smokes Blends lives next to the person with the pet cat.
- The person with the pet horse lives next to the one who smokes Dunhill.
- The person who smokes BlueMaster drinks beer.
- The German smokes Prince.
- The Norwegian lives next to the blue house.
- The person who smokes Blends has a neighbor who drinks water. (Albert Einstein)
Hardest Famous Riddles: Answers
- A human being: An infant crawls (“four legs”), at mid-life (“noon”) walks on two legs, and uses a cane or walking stick (“three legs”) in old age.
- Courtship.
- One: only the storyteller is going to St. Ives, everyone else was already there.
- Time.
- The German owns the pet fish.
Hard Riddles Of The Sphinx: Questions
- There are two sisters: one gives birth to the other and she, in turn, gives birth to the first. What are they? (Oedipus Rex, Sophocles)
- I never was, am always to be. No one ever saw me, nor ever will, and yet, I am the confidence of all who live and breathe. What am I? (Gods of Egypt)
- First think of the person who lives in disguise, / Who deals in secrets and tells naught but lies, / Next tell me what’s always the last thing to mend, / The middle of middle and end of the end? / And finally give me the sound often heard, / During the search for a hard-to-find word. / Now string them together, and answer me this, / Which creature would you be unwilling to kiss? (Harry Potter and the Goblet of Fire, J.K. Rowling)
Hard Riddles Of The Sphinx: Answers
- Day and Night.
- Tomorrow.
- Spyder (spider).
Hard Riddles From Pop Culture: Questions
- My first, I would venture for. My second, I would venture in. My whole is more talked of than practiced. (Bridgerton)
- My first wettens the wilds to create new life. My second adorns a young girl’s hair until she becomes a wife. My whole can lead to pots of gold, ending years of strife. (Bridgerton)
- My first is nothing but a name. My second’s still more small. My whole of so much smaller fame, it has no name at all. (Bridgerton)
- What has roots as nobody sees / Is taller than trees / Up, up it goes / And yet never grows? (The Hobbit, J.R.R. Tolkien)
- Voiceless it cries / Wingless flutters / Toothless bites / Mouthless mutters. (The Hobbit, J.R.R. Tolkien)
- This thing all things devours; / Birds, beasts, trees, flowers; / Gnaws iron, bites steel; / Grinds hard stones to meal; / Slays king, ruins town, / And beats mountain down. (The Hobbit, J.R.R. Tolkien)
- Tear one off and scratch my head. What once was red is black instead. (Batman Forever)
Hard Riddles From Pop Culture: Answers
- Friendship.
- Rainbow.
- Nameless.
- A mountain.
- Wind.
- Dark.
- A match.
Hard Historic Riddles: Questions
- A vessel have I, that is round as a pear, moist in the middle, surrounded with hair; and often it happens, that water flows there.
- Tell me, what is that fills the sky and the whole earth and tears up new shoots, and shakes all foundations, but cannot be seen by eyes or touched by hands?
- I’m soft as wool, soft as a bog. When I swell up, I’m like a frog. I grow in water, where I plunge.
- I am sought by those who seek to change, Yet remain myself, untouched, unstrange. What am I, that can make men rich or dream, Found deep below, by mountain stream?
Hard Historic Riddles: Answers
- An eye.
- Wind.
- A sponge.
- Gold.
Hard Classic Riddles: Questions
- I never was, am always to be. No one ever saw me, nor ever will. And yet I am the confidence of all, To live and breath on this terrestrial ball.
- At night they come without being fetched. By day they are lost without being stolen.
- The one who makes it, sells it. The one who buys it, never uses it. The one that uses it never knows that he’s using it.
- The more you have of it, the less you see.
- You throw away the outside and cook the inside. Then you eat the outside and throw away the inside. What did you eat?
- I am always hungry, / I must always be fed, / The finger I touch, / Will soon turn red.
- Each morning I appear to lie at your feet, / All day I will follow no matter how fast you run, / Yet I nearly perish in the midday sun.
- You saw me where I never was and where I could not be. And yet within that very place, my face you often see. What am I?
- Say my name and I disappear. What am I?
Hard Classic Riddles: Answers
- The future.
- Stars.
- A coffin.
- Darkness.
- An ear of corn.
- Fire.
- Shadow.
- A reflection.
- Silence.
Hard Riddles About Words And Letters: Questions
- I know a word of letters three. Add two, and fewer there will be!
- Two in a corner, one in a room, zero in a house, but one in a shelter. What am I?
- Every dawn begins with me / At dusk I’ll be the first you see / And daybreak couldn’t come without / What midday centers all aboutDaises grow from me, I’m told / And when I come, I end all cold / But in the sun I won’t be found / Yet still, each day I’ll be around.
- It’s true I bring serenity, / And hang around the stars / But yet I live in misery; / You’ll find me behind bars / With thieves and villains I consort / In prison I’ll be found / But I would never go to court, / Unless there’s more than one
- My first is twice in apple but not once in tart. My second is in liver but not in heart. My third is in giant and also in ghost. Whole I’m best when I am roast. What am I?
- This is a most unusual paragraph. How quickly can you find out what is so unusual about it? It looks so ordinary you’d think nothing was wrong with it — and in fact, nothing is wrong with it. It is unusual though. Why? Study it, think about it, and you may find out. Try to do it without coaching. If you work at it for a bit it will dawn on you. So jump to it and try your skill at figuring it out. Good luck — don’t blow your cool!
- I am a word of meanings three. Three ways of spelling me there be. The first is an odor, a smell if you will. The second some money, but not in a bill. The third is past tense, a method of passing things on or around. Can you tell me now, what these words are, that have the same sound?
- 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?
Hard Riddles About Words And Letters: Answers
- Few.
- The letter “R.”
- The letter “D.”
- The letter “S.”
- Pig.
- The letter “E,” the most common in the English language, is not found in the entire paragraph.
- Scent, cent, sent.
- Heroine.
Hard Riddles About Animals: Questions
- A horse walks a certain distance each day. Two of its legs go 30 miles each day and the other two legs go nearly 31 miles. The horse is normal, so how is this possible?
- I grow down as I grow up. What am I?
- A woman stands on the side of a river, her cat on the other. The woman calls to the cat, who immediately crosses the river without getting wet, and without using a bridge or a boat. How did the cat do it?
- What’s at the head of an elephant and the tail of a squirrel?
- A cowgirl rides into a city on Friday, stays for three days, and leaves on Friday. How is this possible?
- A black dog is lying in an intersection in a town painted black. No street lights are working due to a power failure. A car with broken headlights drives toward the dog but turns in time to avoid hitting him. How did the driver see the dog?
- What wears a coat in the winter and pants in the summer?
Hard Riddles About Animals: Answers
- The horse operates a mill and travels in a circular clockwise direction. The two outside legs travel farther than the inside ones.
- A goose.
- The river was frozen.
- “el.”
- Her horse’s name is Friday.
- It was daytime.
- A dog.
Hard Riddles To Tell Your Friends: Questions
- What loses its head in the morning and regains it at night?
- What has one eye but cannot see?
- I have cities, but no houses. I have mountains, but no trees. I have water, but no fish. What am I?
- What is seen in the middle of March and April that can’t be seen at the beginning or end of either month?
- If three cats can eat three rats in three minutes, how long will it take 100 cats to eat 100 rats?
Hard Riddles To Tell Your Friends: Answers
- A pillow.
- A needle.
- A map.
- The letter “R.”
- Three minutes: each cat can eat one rat in three minutes.
Hard “Gotcha” Riddles: Questions
- Paul’s height is six feet, he’s an assistant at a butcher’s shop, and wears size 9 shoes. What does he weigh?
- In British Columbia, you cannot take a picture of a man with a wooden leg. Why?
- How can you drop a raw egg from a height onto a concrete floor without cracking it?
- What part of the turkey has the most feathers?
- Three different doctors said that Paul is their brother yet Paul claims he has no brothers. Who is lying?
Hard “Gotcha” Riddles: Answers
- Meat.
- You can’t take a picture with a wooden leg, you need a camera.
- Concrete floors are very hard to crack.
- The outside.
- No one is lying, the doctors are Paul’s sisters.
Hard Riddles About Numbers: Questions
- How can the number four be half of five?
- How is seven different from the rest of the numbers between one and 10?
- Using only addition, add eight 8s to get the number 1,000.
- How can you make six into an odd number?
Hard Riddles About Numbers: Answers
- IV: The Roman numeral for four is half the letters in the word “five.”
- Seven has two syllables, the others have one.
- 888 + 88 + 8 + 8 + 8 = 1,000.
- Remove the letter S and you have IX which is nine in Roman numerals.
Hard Logic-Following Riddles: Questions
- A is the brother of B. B is the brother of C. C is the father of D. So how is D related to A?
- What are the next three letters in this combination? OTTFFSS
- If all Wibbles are Criggles, all Borkins are Kwumblins, no Hoggles are Borkins, and all Criggles are Borkins, is it true that all Borkins are Criggles?
Hard Logic-Following Riddles: Answers
- A is D’s uncle.
- E, N, T: Each letter is the first letter of the written numbers: One, Two, Three, Four, Five, etc.
- No.
Hard Riddles With Simple Answers: Questions
- What can a child make but never see?
- What has five fingers, but no hand?
- What has 13 hearts and no other organs?
- What can run but never walk?
- Which room has no doors and no windows?
- What can be lost, but never returned?
- What goes Z to A?
- Nobody has ever walked this way. Which way is it?
- What has 10 letters and starts with gas?
- Walk on the living, they don't even mumble. Walk on the dead, they mutter and grumble. What are they?
- A ball has nothing attached to it, there is no one to throw it back, and it doesn't bounce off of anything. How can one throw the ball as hard as they can and always have it come back to them?
Hard Riddles With Simple Answers: Answers
- Noise.
- A glove.
- A deck of cards.
- A river.
- A mushroom.
- Life.
- Zebra.
- The Milky Way.
- An automobile.
- Leaves.
- Throw it straight up.
Confusing Hard Riddles: Questions
- What is it that given one, you’ll have either two or none?
- A man runs away from home. He turns left but keeps running. After some time, he turns left again and keeps running. He later turns left once more and runs back home. Who was the man in the mask?
- I have three feet, but I can’t stand without leaning. I have no arms to hold me up. What am I?
- What connects two people, but touches only one?
- What has a neck but no head, two arms, and no hands?
- You get thrown into a hole. The hole is 30 feet deep, six feet wide and has a little bit of water on the bottom. You can't climb it, you can't dig through it, you can't call for help. How do you get out?
Confusing Hard Riddles: Answers
- A choice.
- A baseball player.
- A yardstick.
- A wedding ring.
- A shirt.
- You wait to be pulled back up by the rope because you’re a bucket tossed down a well for water.
Hard Riddles That Must Be Spoken To Work: Questions
- One knight, a ninja, and a pirate are on a boat. The boat crashes. The pirate jumps of first, the ninja jumps off second, who jumps off third?
- Thirty pigeons, 20 ate crackers. How many didn't?
- There were 30 people in a swimming pool. All 30 people went underwater and when they came back up, there were 30 foreheads. How is that possible?
Hard Riddles That Must Be Spoken To Work: Answers
- The knight: spoken, it will sound like you said “one night.”
- Ten: spoken, it sounds like “30 pigeons, 28 crackers...”
- One forehead per person: spoken, it sounds like “34 heads.”
Silly But Hard Riddles: Questions
- A man drove from New York City to Los Angeles in four days. At the end of his trip, he discovered that one of his tires had been punctured. How was he able to make the drive?
- What came first, the chicken or the egg?
- How can a girl go 25 days without sleep?
- What makes you, young?
Silly But Hard Riddles: Answers
- It was his spare tire.
- Dinosaurs laid eggs much before the evolution of chicken.
- She sleeps at night.
- Adding the letters “ng.”
