6 Hardest Riddles to Answer

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Riddles are fun puzzles that use statements, questions, or phrases that usually have double, or veiled, meanings. Those who enjoy critical thinking enjoy the vague questions that push you to think of possible solutions to what pose to be difficult questions, only to find out that the answer is relatively easy to come up with.

Most individuals who work on riddles enjoy overthinking and might believe them too difficult. But what of the hardest riddles in the world? If you want to train your brain today, try figuring out these top 6 hardest riddles. The answer will be given at the end of each riddle listed.

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What Makes a Riddle Hard?

Riddles are wonderful puzzles that use wordplay and misdirection to stump their opponents. Riddles are used throughout media, from TV shows to books, and while most of them aren’t the hardest riddles to answer, they still can make the viewer or reader think.

The ability to use the right language that creates double meanings and vaguely hinted clues can really make a riddle hard. But for those who enjoy riddles, it’s best to approach the riddle in an unconventional way and think outside the box to really get the answer you’re looking for.

Tips to Solve Riddles

As mentioned, riddles are often simple metaphors that use wordplay and misdirection to challenge you. Most of the time, you overthink the answer. The misdirection sends you into a spiral of potential answers, but once you hear the answer, it’s obvious. Thinking of alternative meanings can really help you understand the problem as well. Instead of reading the clue and going to exactly what you’re thinking, imagine other scenarios where the riddle could be possible.

For example: There was once a soldier who had a brother who was wounded in battle. But the wounded man did not have a brother. How could that be?

You might immediately think of two brothers, with one of them being wounded. The immediate assumption is that both soldiers are male, but if you just think of alternative routes that the riddle could be possible, then you’ll finally figure out that the soldier was female.

6 Hardest Riddles to Answer

6. 1000 Bucks

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Riddle: A man told his son that he would give him $1,000 if he could accomplish the following task. The father gave his son ten envelopes and a thousand dollars, all in one-dollar bills. He told his son, “Place the money in the envelopes in such a manner that no matter what number of dollars I ask for, you can give me one or more of the envelopes, containing the exact amount I asked for without having to open any of the envelopes. If you can do this, you will keep the $1,000.” When the father asked for a sum of money, the son was able to give him envelopes containing the exact amount of money asked for. How did the son distribute the money among the ten envelopes?

Answer: The contents of the ten envelopes (in dollar bills) should be as follows: $1, 2, 4, 8, 16, 32, 64, 128, 256, 489. The first nine numbers are in geometrical progression, and their sum, deducted from 1,000, gives the contents of the tenth envelope.

5. Lazy Daughter

Riddle: A wealthy wise old woman feared that her daughter was lazy and as a result, rather stupid. When the old woman died, her will stipulated that her assets were to be liquidated and a check was to be written for the full amount. The check was to be placed in one of three envelopes. The other two envelopes would contain a blank piece of paper. If the daughter could determine from the writing on the envelope which envelope contained the check, she would inherit her mother’s fortune. Otherwise, the fortune would go to the old woman’s favorite charity for animals.

The daughter was not allowed to touch the envelopes. Her decision had to be made based on the writing on the envelopes. The daughter was told that only one envelope had a true statement and that the other two statements were false. The envelopes had the following writing: 1. This envelope does not have the check. 2. This envelope has the check. 3. The second envelope does not have the check. Which envelope should the daughter pick?

Answer: The daughter should pick up envelope 1. Unfortunately, she picked envelope 3. Statements 1 and 2 were false, and the only true statement was statement 3. If the check was in envelope 1, that would make statement 1 false, statement 2 false, and statement 3 is the only true statement. If the check was in envelope 2, statements 1 and 2 would both be true. If the check was in envelope 3, statements 1 and 3 would both be true.

4. Three Working Women Have Different Careers

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Riddle: Three working women have different careers. If only one of statements 1, 2, and 3 are true, can you tell whether or not Mary is a nurse? 1. This statement is only true if statement 5 is false. 2. This statement is true if statements 4 or 5, or both 4 and 5 are true. 3. This statement is false only if both statements 6 and 1 are true. 4. Mary is a nurse 5. Karen is an artist. 6. Sarah is a photographer.

Answer: Mary is not a nurse. The way to solve this riddle is to consider statements 4, 5, and 6 and create a chart of all possible true and false answers. Next, fill in the chart according to statements 1 through 3. You will discover that there is only one line where only one of the statements one, two, and three are true. Thus, it is determined that: Statements 4 and 5 are false and statement 6 is true.

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3. Getting Away with Manslaughter

Riddle: Two cars were involved in an accident in the center of town. The man who was driving a little green car had overtaken a big black car. The driver had misjudged the distance between him and the on-coming traffic and had to swerve back in, causing the black car to swerve and crash into a shop window. When the occupants of the cars were examined everyone in the green car was okay, but one dead man in the black car. However, the driver of the green car was not charged with manslaughter, why was this so?

Answer: The black car was a hearse and was on its way to a funeral.

2. Tell Us the Day!

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Riddle: A group of campers have been on vacation so long, that they’ve forgotten the day of the week. The following conversation ensues.

Darryl: What’s the day? I don’t think it is Thursday, Friday or Saturday. Tracy: Well that doesn’t narrow it down much. Yesterday was Sunday. Melissa: Yesterday wasn’t Sunday, tomorrow is Sunday. Ben: The day after tomorrow is Saturday. Adrienne: The day before yesterday was Thursday. Susie: Tomorrow is Saturday. David: I know that the day after tomorrow is not Friday. If only one person’s statement is true, what day of the week is it?

Answer: It is Wednesday. If it was any other day of the week, more than one statement would be true. To solve the riddle, evaluate each person’s statement and write down what day it could be according to the statement. David’s statement indicates it could be any day of the week except for Wednesday. When you list the days that it could be according to everyone’s statement, it turns out Wednesday is the day mentioned only one time. Darryl: Sunday, Monday, Tuesday, or Wednesday Tracy: Monday Melissa: Saturday Ben: Thursday Adrienne: Saturday Susie: Friday David: Sunday, Monday, Tuesday, Thursday, Friday or Saturday.

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1. You Walk Up to a Mountain That Has Two Paths

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Riddle: You walk up to a mountain that has two paths. One leads to the other side of the mountain, and the other will get you lost forever. Two twins know the path that leads to the other side. You can ask them only one question. Except! One lies and one tells the truth, and you don’t know which is which. So, What do you ask?

Answer: You ask one twin,  “Are you twins?”. If he says “Yes”, he is telling the truth.  Therefore, you ask the other twin which way to go and go the opposite way because he is lying. If he says “No”, he is the liar and you ask the other twin which way to go because he is telling the truth.

Nikole Stewart is a writer and editor with three years of experience writing keen articles on topics such as... More about Nikole Stewart

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