70 Most Confusing Questions Anyone Would Find Unanswerable

One of the ways through which people try to gauge the intelligence of others is by asking confusing questions that make the mind wander aimlessly. These types of questions that are usually riddles or unanswerable questions are designed to trick you, as well as make you think outside the box as you wonder what the answer could be.

Not all confusing questions have intelligence identifying motives though as people might choose to ask confusing questions that are unanswerable as a way to have fun. Others may do so because they lack a better way of structuring their questions. Whatever the case is, asking a confusing question can lead to a whole lot more than what was desired. It could serve as a great conversation starter, a way to work out your brain and that of others around you, or simply just a way to have fun.

What Makes a Question Unanswerable?

Questions should generally be answerable and are asked to elicit information. People ask questions in order to find out something they do not know. When questions are asked, a response that comes in the form of an answer to what was asked is expected. Unless circumstances are different than usual, answers to general questions are not supposed to cause you any stress and should be straightforward. More or less, a yes or no answer should suffice.

Confusing questions, on the other hand, are generally unanswerable. As stated earlier, they are designed to make your mind wander aimlessly. They do not have a direct answer as two or more people who are asked the same question can give totally different answers to the same thing. These answers may not match the general perception of reality, may not make sense or could be unpopular, are blatantly false or unuseful, or just do not provide the information that the asker is seeking. This is what makes it a good way to gauge intelligence or a way to have fun as the different answers it elicits can tell how the brain of the person functions, something that would be more or less entertaining to a group of people.

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To be able to ask an unanswerable question, however, there are a few things that you would want to have in mind that when incorporated in the question, would make it quite unanswerable.

1. Add more than one variable: Questions that have more than one moving part would mean different things to different people. This would make it difficult to answer accurately.

2. Ensure that the person being asked the question lacks the necessary knowledge to provide the answer.

3. Ask completely subjective questions whose answers are based solely on preference. A good example is the “pineapple as a pizza topping” question.

4. Ask philosophical questions that can either have no true answer or have many answers. Even if there is a true answer, it is one that is likely to be understood by only a small number of people who have specialized knowledge or interest in the subject.

5. Choose questions that are rhetorical and are never meant to have an answer.

6. Ask questions whose answers are unknowable. Such questions may be like asking if there is a God and what happens to people in the afterlife, etc.

With this in mind, we have put together some of the most confusing questions ever that will certainly have you cracking your brain trying to figure them out.

The Most Confusing Unanswerable Questions

25 Funny Confusing Questions

1. Can you talk down to someone who is taller than you?

Obviously, you can talk down to anybody but you would have to be looking up when doing so to a tall person.

2. What hair color is written on the driver’s license of bald people?

Perfect question to ask a bald person and see them wander about it.

3. What is a fly without its wings called?

A walk? A jump? A crawl? An insect? Different people would definitely give you different answers.

4. Which orange came first – the fruit or the color?

Which is named after the other? and do they have any similarities we do not know of?

5. What would happen if Pinocchio said his nose will grow now?

Pinocchio’s nose grows when he lies. So when he says his nose will grow now, he is prompting his nose to grow, which then isn’t a lie. People would give you different explanations about this.

6. Why isn’t there a mouse-flavored cat food if mice are the favorite food of cats?

It only makes sense to create a flavor of their favorite kill.

7. Why is the number 2 pencil more popular than number 1?

One has always been higher than two. Why doesn’t this apply to pencils?

8. Why is the second hand in a watch the third hand?

A great follow-up question to the one above.

9. Do you become the waiter when you wait for the waiter in the restaurant to bring your order?

When waiting you are a waiter, there are no two ways about it.

10. Is the word “dictionary” defined in the dictionary?

It should but is it?

11. Why are existing houses/structures called buildings but not built?

Is it cause there is always room for improvement? Everyone has a funny answer to give.

12. What kind of tree can you carry in your hand?

None! But your palm is in your hand and there is a tree called palm tree. A few people might be clever enough to answer this.

13. If you throw a blue pebble into the red sea, what would it come back as?

Remember that you are not supposed to overthink things. The rock comes back wet, however, a few might try to be clever and overthink it.

14. Which is faster between heat and cold?

Heat, because people often catch a cold.

15. When does a door stop being a door?

A door is always a door, however, you could say it stops being so when it is a Jar (ajar)

16. Name one room that has no walls?

A mushroom

17. What woman can never be wrong about the present location of her husband?

A widow

18. Is it wrong for a man to marry his widow’s sister?

The man must be dead if it is his widow’s sister. So technically, he can’t do so.

19. Name two keys that cannot open any door in the world?

Don’t overthink it. The answer could be a donkey and a monkey.

20. What combined two words have all the letters?

Post and Office. All letters go through the post office.

21. What letter in the alphabet stings and sings?

“B” for Bee

22. Who has married many people but has never actually been married?

The pastor/minister

23. What is always answered but never has a question?

When the doorbell rings, you answer it without any questions.

24. In what situation can four people stand under one normal-sized umbrella and not get wet?

When it is not raining.

25. What stays in the same place but goes up and down?

They probably use stairs everyday but would never have guessed it.

25 Confusing Philosophical Questions

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1. When did time begin and who began measuring it?

Questions do not get more philosophical than this as the bible and greek methodology come into play.

2. How are seedless fruits grown?

Fruits are grown from seeds and seeds are gotten from the fruit. So if the fruit is seedless, how is it grown?

3. If tomatoes are considered a fruit, why isn’t ketchup considered a smoothie?

Why are tomatoes fruit and not vegetables? A whole lot more can be unearthed with this question.

4. They say good things come to those who wait. So why does the early bird get the worm?

The early bird gets the worm while the other bird waits, so what good thing is going to come to the bird that waits.

5. The fountain of youth allows people to live forever. What happens if you drown in it?

Yes, it is made up of water but can one even drown in something that is supposed to give everlasting life?

6. Are we truly free if we are to live by rules?

There are laws and other rules and regulations that people should abide by but we are supposed to be free people. How so?

7. Are eyebrows considered facial hair?

By definition, facial hair is any hair that appears on your face. So, why aren’t eyebrows considered so?

8. Why does the rain drop and snow fall when they both come down from the sky?

One is heavier than the other but who measured it to determine? Another question to follow up with.

9. Why did humans agree to give February 28 days while the other months have either 30 or 31 days?

Another lesson in history commences, that is if anyone knows.

10. If your neighbor’s peacock lays an egg on your property, who owns the egg?

I bet they don’t know that Peacocks don’t lay eggs.

11. How many times can 10 be subtracted from 100?

This can only be done once, since the next time you would be doing so it would be from 90.

12. How many animals got into the ark with Moses?

This question is dead on arrival if they are able to identify that it was Noah who built the ark and not Moses.

13. If you pass the person in second place while running a race, what position would you be in?

Second place. You will need to pass the person in the first place to be first.

14. What can you break without holding it?

A promise can’t be held but is treasured and can be broken.

15. When can there be something in your pocket, and also nothing in it?

When there is a hole in the pocket.

16. What can you hold but not touch?

You definitely can’t touch a conversation but can hold one.

17. What can you make that no one can see but can hear?

Noise. It can be heard but cannot be seen.

18. What do you own that is used by everyone else but rarely gets to be used by you?

Your name. People say it more than you would ever say it.

19. What is so fragile that when you say a word, you break it?


20. What item does the maker not want, the buyer not use, and the user not see?

A coffin. The user doesn’t see it because when it is bought, he/she is most likely dead.

21. Is it possible to live life to the fullest?

Do we truly know our potential as humans? Does potential vary from human to human? Who ultimately decides?

22. Are there any limitations to free speech?

Freedom of expression is regarded as a fundamental human right. However, many governments and people in power have punished many that exercise this right. Why is this so?

23. When children are born, are they good or evil?

It is either one or the other. Whichever way the question is answered, they can try to explain how either being good or being evil is learned.

24. Is the life of one human worth more than that of another?

A religious person might answer that all human life is worth the same but many others would argue that one human’s achievements determine this.

25. Can our emotions be selected/chosen or do they just happen involuntarily?

This is tricky because the emotion of anger and the emotion of happiness have different things that prompt them. One can choose to be happy when they are being angered, but can they choose to be angry in the face of happiness?

20 Confusing Questions That Have No True Answer

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1. At what age does someone qualify to die of old age?

70? 75? 80? 100? Some might even say 120!

2. How do you know everything happening around you right now is not a figure of your imagination?

What is life, humanity, and how do we know we are not in a trance?

3. Are people who die wearing braces buried with them?

If you are not asking a mortician or any medical personnel, this is a perfect confusing question to ask to get the mind wandering.

4. Why is bacon cooked and cookies baked?

The method of preparation is different from the name, why?

5. Why do noses run and feet smell?

Great follow-up question the one above.

6. Is it possible to truly differentiate between good and evil?

Good and evil have been argued to be relative to one’s culture, society, and religion. But our conscience should be able to tell, no?

7. Why are people afraid to make mistakes when you can only learn from making a mistake?

You can’t be willing to learn without being able to handle failure. However, people learn without making mistakes. How?

8. Doesn’t it make you a hater if you hate haters? And are you supposed to hate yourself as a result?

Good luck finding a true answer to this question.

9. Why do monkeys still exist if science says we evolved from them?

Yes, we all missed science class. Can someone please explain this?

10. What happens when a human being dies?

Unless the person is religious, this is a great confusing question that would get one or two people going.

11. Is the planet earth a living or non-living thing?

The world is made up of living and non-living things. Which side does the earth fall in?

12. If someone takes your advice to “be a leader and not a follower”, wouldn’t they technically be a follower by following your advice?

Don’t follow what anybody says, but follow what I say.

13. Why is pepper in some parts of the world called “chili” when it is hot?

Chilly is supposed to mean cold but not in this case.

14. Why is it called Life Insurance when it is only redeemable when one is dead?

Death Insurance would sound attractive now, would it?

15. If a dairy cow is pampered, do you get spoiled milk from it?

They say if something is pampered too much, it gets spoiled. I wonder if it applies in this case.

16. Are human beings living or just slowly dying?

We all die eventually don’t we? So why do they say to live life to the fullest when we get closer to our death bed with each passing day.

17. Why did Cinderella’s shoe fall off if it fit her perfectly?

Shoes aren’t supposed to fall off if they fit perfectly. Find out what explanations your audience might have.

18. People should not drink and drive so why are they sold alcohol after presenting their driving license as an ID?

You clearly drove to the bar if you are presenting your driver’s license as a form of identification when buying alcohol. That should automatically disqualify you from buying a drink, should it?

19. Is time wasted when you enjoy wasting time?

People enjoy doing nothing, which is technically wasting time since you could be doing something productive. SO, since that time doing nothing was enjoyable, was it time-wasting?

20. What is the color of the mirror?

What if the mirror is actually a color. Who knows?


If your intention is to gauge a person’s level of reasoning by asking confusing questions, then, by all means, ask to see how they interpret it. However, if it is in regard to a survey or test, where the answers would be used in determining something of importance and usefulness, then it is best to avoid asking anything that would make the respondent confused. This is because the answers would not be accurate and therefore cannot be used to determine the ability or be regarded as an accurate reflection of the response required.

Chizzy Onukogu
Chizzy Onukogu
Chizitere is a writer and editor with over five years of experience in producing articles on various subjects. My writings have been published on multiple websites and publications


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