40+ Long, Funny & Challenging Riddles and Brain Teasers

Easy Long Riddles

I went to London, Paris, Tokyo, and Shanghai, and I have been to Rome. I could go to India, but sometimes I get sent home—and I do all of this by simply sitting in a corner. What am I? Answer: A stamp.

In a one-story house at the corner of the road, the bedrooms were yellow, the kitchen was orange, the living room was red, the garage was blue, the entry hall was green, and the sitting room was purple. What color were the stairs? Answer: There’s no color because there are no stairs—it’s a one-story house!

Benjamin was out for a walk when it started to rain. He did not have an umbrella, and he wasn't wearing a hat. His clothes got soaked in the rain, yet somehow, not a single hair on his head got wet. How could this happen? Answer: Benjamin is bald and, therefore, has no hair to get wet.

A bus driver is heading down the street. He goes right past a stop sign without stopping, turns left where there’s a "no left turn" sign, and goes the wrong way on a one-way street. Then he goes on the left side of the road past a police car. Nonetheless, he didn't break any traffic laws. Why not? Answer: He was walking, not driving, and didn’t have to obey traffic laws.

Jane lives in a place where six months of the year is mild summer, but the temperature drops significantly the other six months. She owns a lake where there is a small island. She wants to build a house on the island and needs to get materials there. She has no boat, plane, or anything to transport them to the island. How does Jane solve this problem? Answer: She waits for the six colder months when the lake will freeze over so she can walk across the ice with her materials.

Chef Karin has to light the kitchen stoves to open her restaurant for the day. There are three stoves in the kitchen: a glass stove, a brick stove, and a wood stove. She only has one match. Which does she light up first? Answer: The match; she can’t light any of the stoves without it.

My first is in chocolate but not in ham. My second is in cake and also in jam. My third at tea time is easily found. Altogether, this is a friend who is often around. What is it? Answer: Cat. “C” is the first letter in chocolate, “A” is the second letter in cake and jam, and “T” is easily found in tea-time.

There was a competition where the contestants had to hold something. At the end of the event, the winner was a person with no hands or feet. What was it that the contestants had to hold? Answer: Their breath.

Funny Long Riddles

I can sizzle like bacon, I am made with an egg, I have plenty of backbone, but lack a good leg, I peel layers like onions, but still remain whole, I can be long, like a flagpole, yet fit in a hole. What am I? Answer: A snake.

A pet shop owner had a parrot with a sign on its cage that said "This parrot repeats everything it hears". Jonathan bought the parrot and for two weeks he spoke to it and it didn't say a word—so he complained to the shop owner, who said he didn’t lie. How is this possible? Answer: The parrot is deaf and doesn’t hear anything.

A boy was at a carnival and went to a booth where a man said, "If I write your exact weight on this piece of paper, you have to give me $50, but if I can’t, I’ll pay you $50." The boy looked around and saw no scale, so he agreed, thinking no matter what the man wrote, he'd just say he weighs more or less. However, the boy ended up paying the man $50. How did the man win the bet? Answer: He wrote “Your exact weight” on the paper (because that’s exactly what he said he would do).

Two boys are born to the same mother, on the exact same day, at the exact same time, in the exact same month and year. Nonetheless, they are somehow not twins. How is this possible? Answer: They’re part of a set of triplets.

It spends most of its day eating white, but when it’s quick enough, it gets to eat fruit and sometimes some blue things. It’s in a dark room, where the walls are blue, it runs from a ghost that roams the halls and haunts it all the time. What is it? Answer: Pac-man!

A student asked his teacher, "Miss, is it fair if I get in trouble for something I did not do?" The teacher replied, "Of course not! Tell me who got you in trouble for something you didn't do?" So, what did the student then reply with? Answer: “I forgot to do my homework again!”

In marble walls as white as milk, lined with skin as soft as silk, within a fountain crystal clear, a golden apple does appear. No doors are there to this stronghold—yet thieves break in and steal the gold. What is it? Answer: An egg.

You walk into a room and see a bed. On the bed, there are two dogs, five cats, a giraffe, six cows, and a goose. There are also three doves flying above the bed. How many legs are on the floor? Answer: Six. The bed has four legs and you have two, which equals six.

Long Riddles with Numbers

A man wants to get into an exclusive club but doesn’t know the password. A woman approaches the door and the doorman says 12, so the woman says 6, and is let in. Another woman walks up and the doorman says 6, so the woman says 3, and is let in. Thinking he’s figured it out, the man walks up to the door, and the doorman says 10, so he says 5 but isn’t let in. What should he have said? Answer: 3. The code for the door is the number of letters in the number the doorman says.

There’s a farmer, and someone asks her about the animals on her farm. In reply, the farmer says, “I only ever keep sheep, goats, and horses. In fact, at the moment they are all sheep bar three, all goats bar four, and all horses bar five.” How many of each animal does the farmer have? Answer: The farmer has three sheep, two goats, and one horse. To solve it: You know that three animals are goats and horses, four are sheep and horses, and five are sheep and goats. Using that logic, you can hypothesize that there are two goats and one horse, which checks out because the four non-goats are three sheep and the horse.

Two fathers and two sons went fishing together. They were there the entire day, but they only caught three fish. One father said, “That will be enough fish for all of us; we’ll have one each.” How can this be possible? Answer: There are only three people: the father, his son, and his son’s son—which equals two fathers and two sons.

There are 25 red balls, 47 green balls, and 3 blue balls in a basket. There is a blindfolded man. What is the minimum number of balls that the blindfolded man has to pick to make sure that there are at least 2 balls of different colors? Answer: 48 balls. There’s a very small chance he could pick up 47 green balls in a row, so to be sure, he’d have to pick up 48.

A dog wants to get in better shape. She’s going to start by climbing the stairs. Starting on the fourth floor, she climbs up five stories, down seven stories, up six stories, down three stories, and up four stories again. What floor is the dog on? Answer: The 9th floor.

Long Wordplay Riddles

I weaken all people for hours each day. I show you strange visions while you are away. I take you by night, and by day, take you back. None suffer to have me, but do from my lack. What am I? Answer: Sleep.

I can be winding, and I can be straight. I can be smooth or rough—sometimes both. I start out black but fade to brown the more I am used. My favorite colors are yellow and white, and I love stripes and dashed lines. What am I? Answer: A road.

I cannot be seen and cannot be felt; cannot be heard and cannot be smelt. I lie behind stars and under hills; all empty holes do I fill. I come first and follow after. I end all life and kill all laughter. What am I? Answer: The darkness.

The first two letters signify someone who is male. The first three letters signify someone who is female. The first four letters signify a great person—but the entire word signifies a great woman. What word is it? Answer: Heroine.

A woman shoots her husband and then holds him underwater for five minutes. Next, she hangs him—but then they enjoy a lovely dinner together right after that. How is this possible? Answer: She took a photograph of him and developed it in a darkroom before dinner.

Pronounced as one letter and written with three, two letters there are, and two only in me. I’m double, I’m single, I’m black, blue, and gray, I’m read from both ends, and the same either way. What am I? Answer: An eye.

I may be simple or I may be complex; I may have a name but no gender or sex. I am often a question or statement as a setup; I tend to have an answer, and until you find it, I won't let up. What am I? Answer: A riddle!

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, and in prison, I’ll be found. But I would never go to court unless there’s more than one. What am I? Answer: The letter “S.”

There is one word that stands the test of time and holds fast to the center of everything. Though everyone will try at least once in their life to move around this word, they unknowingly use it every moment of the day. Young or old, awake or asleep, human or animal, this word stands fast. It belongs to everyone, to all living things, but no one can master it. The word is? Answer: Gravity.

I am a five-letter word, and people eat me. If you remove the first letter, I become an energy form. If you remove the first two letters, I am needed to survive. Scramble the last three letters, and I am a drink. What word am I? Answer: Wheat. Removing the first letter turns it into “Heat,” and removing the first two turns it into “Eat.” When you scramble the letters, they become “Tea.”

I look flat, but I am deep. Hidden realms I shelter. Lives I take, but food I offer. At times I am beautiful. I can be calm, angry, and turbulent. I have no heart but offer pleasure as well as death. No man can own me, yet I encompass what all men must have. What am I? Answer: The ocean.

Hard Long Riddles

There’s an 8-letter word that can have a letter taken away and still be a word. Take another letter away, and it’s still a word. Keep doing that until there’s only one letter left, and it’s still a word every step of the way. What is the original 8-letter word? Answer: “Starting.” Take away the middle “T” and it becomes “Staring.” Take away the “A” and it becomes “String.” Remove the “R” and it becomes “Sting.” Remove the “T” and it becomes “Sing.” Take away the “G” and it becomes “Sin.” Remove the “S” and it becomes “In.” Remove the “N” and it becomes “I.”

A farmer buys a fox, chicken, and bag of corn at the market. On his way home, he comes to a river bank and rents a boat. However, he can only fit himself and one of his purchases on the boat at a time: the fox, the chicken, or the corn. If left unattended, the fox would eat the chicken, or the chicken would eat the corn. The farmer must get everything to the river's far bank with each purchase intact. How does he do it? Answer: The farmer takes 7 trips in total. He must bring a purchase back across the river to make this possible. His trips are: 1. He brings the chicken across. 2. He returns. 3. He brings the fox or corn over. 4. He returns with the chicken. 5. He brings the corn or fox over. 6. He returns. 7. He brings the chicken across.

You’re trapped in a dungeon with two doors and two guards. Door A leads to freedom, while door B leads to death. You don’t know which door is which, but the guards do. Also, one of the guards always tells the truth, while the other always lies—but you don’t know which is which, either. You can ask the guards a single question, so how do you find the door leading to freedom? Answer: You ask one of the guards (it doesn’t matter which one) which door the other would say leads to freedom. That’s because: If it’s the liar guard, they’d falsely say that the other guard would point to door B. If it’s the truth-telling guard, they’d truthfully say the other guard would point to door B as well. Therefore, regardless of which guard you ask, you can safely deduce that door A is the safe door and door B is the deadly one.

This is a most unusual paragraph. How quickly can you find out what’s 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’s 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’ll dawn on you. Jump to it and try your skill at figuring it out. Good luck—don’t blow your cool! Answer: The letter “E” is the most common letter in the English language, yet it’s not in the paragraph at all.

A father needed to decide which of his kids would inherit his property. To test them, he said, “Go to the market and buy something large enough to fill my bedroom, but small enough to fit in your pocket.” The first child laid some cloth across the room, but it barely covered the floor. The second child laid hay on the floor, but there was only enough for half. When the third came in and showed his father what he brought, he got the property. What did he show his father? Answer: A box of matches. Lighting a match can fill a room with light, yet the box is small enough to fit in a pocket.

There’s a girl who has a large family. She has an equal amount of brothers and sisters, but each brother only has half as many brothers and sisters. So, how many brothers and sisters are actually in the girl’s family? Answer: Four sisters and three brothers. To get this answer, count the number of brothers and sisters in total—including the girl—and then in terms of the number of siblings each would have. So, if the girl has three sisters, that means there are 4 in total (including her). Then, if each brother only has two brothers, that makes 3 in total. Thus, there are 4 sisters and 3 brothers.

One night, a man runs away from home. He turns left and keeps running. After some time he turns left again and keeps running. Later, he turns left one more time and runs back home—but when he gets home, he finds a man in a mask. Who was the man in the mask? Answer: A catcher. They’re playing baseball, which is why the man kept turning left to get to “home.”

The Harvard Riddle

I turn polar bears white and I will make you cry. I make guys have to pee and girls comb their hair. I make celebrities look stupid and normal people look like celebrities. I turn pancakes brown and make your champagne bubble. If you squeeze me, I’ll pop. If you look at me, you’ll pop. Can you guess the riddle? This riddle is known as the “Harvard riddle” because it went viral after 98% of Harvard students couldn’t get it right. Although no riddle is definitively the hardest, this one is sometimes called the “world’s hardest riddle,” too. Answer: “No.” Most of the riddle is meaningless. The only line that matters is the last one: “Can you guess the riddle?” The answer is “No” because nothing fits the rest of the description.

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