60 Crazy and Weird Questions to Ask Your Friends or People Around

The best way to know a person and the inner workings of their mind, as well as their opinions on varying issues, is to ask questions. No matter how long you have known a person, asking crazy and weird questions opens up another layer of them that you may not know about.

Whether it is your best friend, friends, or people around, our list of crazy and weird questions to ask your friends and people around you, will give you interesting things to talk about as well as shine the light on what goes on in their minds.

Crazy and weird questions are suitable for truth or dare games, casual hangouts and picnics, or just a regular conversation to cure boredom. The following questions will always keep your conversations going. 

Weird Questions to Ask Your Best Friend

What is a best friend for if not for inconveniences and freedom to ask weird questions? Having a best friend means having a confidant and someone you can trust to tell even your most embarrassing secrets.

That also means you can always ask them the weirdest of questions to have a good laugh, get to know them better, or simply engage in an interesting conversation. Here are some fun and interesting weird questions to ask your best friend.

60 Crazy and Weird Questions to Ask Your Friends or People Around
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1. What age will you prefer to stay in forever?

This question is one of the easiest ways to find out if there is a particular age your best friend enjoyed being in, the most and wishes to remain in that age forever. 

2. What is the weirdest dream you have ever had?

Dreams happen to be the weirdest things about being alive. Dreams are a whole world of weirdness.

3. If you could exchange lives with one of your siblings, who would it be?

Sometimes, siblings might feel that a particular sibling has a life much easier for them. Find out if your best friend is in that category.

4. What period in history would you prefer to live in?

History records many interesting eras of civilization. From the time of the dinosaurs to the Iron Age. Which would your best friend love to exist in.

5. If you were to turn into food, what food will you turn into?

This is one of the weird ways to find out your best friend’s favorite food.

6. Would you rather live a long but poor or live a short but extremely wealthy life?

What is more important to your best friend? Long-life or long wealth? This is one of those interesting weird questions you can ask your best friend, friends, or people around you.

7. What hair color do bald people list on their driver’s license?

Sharing a few laughs with your best friend should not be far-fetched. This is a silly weird question meant for laughs only.

8. What will you do if you find out you have a long-lost twin?

Finding out that you have a long-lost twin should be a pleasant experience. Find out What your best friend would do.

9. How many times do you think about sex in a day?

This is one of those crazy and weird questions that you can easily ask your best friend. After all, best friends know the weirdest things about each other. You can’t ask this to regular people around you, it may be offensive to them.

10. What secrets are you keeping from me?

Best friends are meant to know each other’s secrets. This weird question will help you find out which of your friend’s secrets you are yet to know.

11. A lifetime supply of booze or a lifetime supply of water?

How healthy are your best friend’s habits? This weird question will help you find out if your best friend has a healthy habit. If he/she chooses booze, then you know that your best friend has no plans of being a health enthusiast.

12. Why are we best friends?

One of the weird questions you can ask your best friend is asking them why they think the both of you are best friends. Find out what your best friend thinks.

13. What is the weirdest food you have ever eaten?

A lot of people have eaten something they consider as weird. Find out which weird ones your best friend has eaten.

14. What is the one thing you would never buy?

You most probably know a list of things your best friend would love to buy or spend their money on. But what about the one thing they would never buy? This is a good weird question that allows you to find out something new about your best friend.

15. To fall asleep, how many sheep do you have to count?

Counting sheep is an idiom for insomnia. This weird question is a funny one that pokes at the age-long idiom of counting sheep.

Weird Questions to Ask Friends When Bored

When it seems like you have run out of things to talk about with your friends, the feeling of boredom starts to set in. However, the following weird questions to ask your friends or people around you can help send boredom away as quickly as it came.

16. Why do cats have nine lives?

Why is it said that cats have nine lives? has a cat died and been resurrected nine times? Time for some discussion on age-old myths.

17. How many times do you poop in a week?

Who counts the number of times they defecate in a week? Except for health reasons, most people do not keep a track of the number of times they empty their bowels and that is why this question is top of the list of crazy and weird questions you can ask your friends or people around you when you are bored.

18. What is the difference between six and half a dozen?

This is a popular weird question that you may have heard before. You can ask your friends or people around you when you are bored and trying to start a conversation.

19. Has anyone ever walked into your fart?

Imagine thinking you have some alone time on your own and you decide to let out a stinky fart and suddenly someone walks into your location while it still stinks of your fart, how embarrassed would you be? This has happened to a lot of people, you can ask your friend this question when you are bored and wondering what to talk about.

20. What is the first thing you would do on your wedding night?

Most people have a lot of plans or fantasies about the things they plan to do on their wedding night. If you are looking for a weird question to ask a friend or people around you when you are bored, this is a good idea.

21. If you woke up to be the only person left on earth, what will you do?

Imagine waking up to a post-apocalyptic world and you are the only human left alive in the whole world, what will you do? This is one of those weird questions that need a lot of thought.

22. Why is it called rush hour when it is the slowest time in traffic?

People spend a usually longer amount of time stuck in traffic during the time of the day known as the rush hour. Why is that so? Why isn’t it called slow hour, since people move slower in traffic?

23. Why is the number 11 not pronounced as “onety one”?

Number 22 is pronounced twenty-two, the same as 33 and 44, and all other double-digit same numbers. Why is 11 different? Why is it pronounced as eleven and not as onety one?

24. The first teacher was the student of who?

Who was the first teacher? And who taught them what they know? This is one of those weird questions that can get your friends or people around you to think hard.

25. At what age do we stop playing with toys?

When exactly does our childhood end? What day did we decide to stop playing with toys and become grown-ups? This is a nostalgic weird question. It can pave the way for a much deeper conversation.

26. How did zoologists know how animals think?

A zoologist is an expert in the behavior of animals. But how did the zoologist know? Did the animals tell them? This is a very funny weird question to ask your friend or people around you. To make it even more fun, you can ask a zoologist.

27. How will a dog wear pants? On its hind legs, forelegs, or both?

Dogs are a man’s best friend and one of the most common pets in several households. Overzealous pet parents usually dress up their dogs in human clothes and as such, if you were to put on a pair of pants on a dog, which of its legs will you put it on? All of its legs or its forelimbs or hind limbs? This is a hilarious weird question, especially for a pet parent.

28. If you won $100 million and your grandpa needs $99 million for life-saving surgery, what will you do?

This is an interesting weird question to ask your friend when you are bored. Will your friend spend almost their entire winnings to save their grandparent or allow their grandparent to die because they are already old.

29. Do you have a different towel for your buttocks or your face?

If you don’t have a different towel for your buttocks or your face, that means the part of the towel that wipes your butt today may be the part that wipes your face tomorrow.

30. How weird are you on a scale of 1-10?

Asking your friend to tell you how weird they are with the use of a scale, is one of the easiest ways to find out just how weird your friend is. This is a good truth or dare question.

Crazy Questions to Ask Your Friends

Crazy questions are questions that are irregular and usually have no definite answer or a question that has a funny answer. When a weird question is turned up a weirder notch, you get a crazy question— just like the following examples:

31. If you have to wait for a waiter, does that make you the waiter?

If you are waiting for something, it means you are a waiter. So if you are waiting for a waiter, it means you both are waiters.

32. Why do banks have branches, if money doesn’t grow on trees?

This is a crazy but funny question. It makes a good joke too.

33. Why is it called the first birthday when it is the second?

When a child becomes one year old, it is called their first birthday, but is it not their second birthday? Because their first birthday is the actual day they were born. Although a crazy question, this is eye-opening.

34. If a deaf person has a court date, will it still be called a hearing?

This is a very funny crazy question to ask your friends or the people around you. Although it may seem a bit offensive, is not meant to cause any offense. This rhetorical question is purely meant to elicit laughter and nothing more.

35. What was the person who discovered milk doing to the cow?

This is a popular crazy and weird question on the Internet, and a good one to ask your friends or people around you. This crazy question is just for laughs.

36. What do humanitarians eat if vegetarians eat vegetables?

Humanitarians do not eat humans but this is a very funny crazy question to ask your friends and a good joke to tell.

37. Why don’t eggs tell jokes?

This is a crazy question and a hilarious joke. The answer is simple. Eggs don’t tell jokes because they will crack each other up. Your friends are going to laugh hard at this question/joke.

38. Where were the native Americans before Columbus discovered them?

This is a sarcastic question that points to the assumption that Christopher Columbus discovered America. If he indeed discovered it, then where did the Native Americans who are the original inhabitants of the land live?

39. Why did the man knock before opening his fridge?

This is another crazy question with an even crazier hilarious answer. Your friends will have a hard time thinking about the answer and if they don’t get it, you can reveal to them that the man knocked before opening the fridge in case there was a salad dressing.

40. If the world has a global debt, who are they owing?

Every nation in the world seems to be owing to something and there are reports of the globe being in debt. So if the whole world is in debt, who are they indebted to? Aliens?

41. If Vegetable oil is made from vegetables, what is baby oil made from?

Another crazy question that is good for laughs and nothing more. Surely baby oil isn’t made out of babies.

42. How do you think about something unthinkable?

Just like describing the indescribable, how can you think about something unthinkable? Maybe the answer is not to think about it at all.

43. If you were to exist on a computer, what software would you be?

This is an interesting question to ask your friends especially if they are techies. Imagine yourself as a software in a computer, what software would you want to be?

44. What organ in your body can you readily donate?

This is a very crazy question because most people do not think about donating their organs on a normal day, that is why this question is one of the crazy questions to ask your friends or people around you.

45. Why did the baker throw the butter out of the window?

This is also one of those crazy questions that will have your friends laughing because the answer is even more hilarious. If they don’t know the answer, you can always tell them that it is because the baker wanted to see the butterfly.

Weird Questions to Ask People

If you want to start a fun and interesting conversation with friends, colleagues, or even people around you, weird questions are good icebreakers. Here are some Hilarious examples to try.

46. If life is unfair to everyone, does that mean life is fair?

If everyone in the whole world suffers their share of misery and unfairness, that means life is fair in doling out unfairness to everyone.

47. Why are we afraid of making mistakes since we also learn from them?

An interesting rhetorical question that questions one of the most popular rhetorics of learning from one’s mistakes.

48. Why are they called apartments when they are built together?

A weird question on one of the many confusing words in the English language. A good one to ask the people around you.

49. Is ketchup a smoothie? Since tomatoes are fruit.

Tomatoes are considered fruit just like how they are considered vegetables. But if they are fruit, does it mean tomato ketchup is a smoothie?

50. If you buy a bigger bed, will you have more bed-room? Or less bed-room?

This is top on the list of weird questions to ask people around you. It will be more fun if asked in a gathering of people. Makes room for a good debate.

51. If time is money, is an ATM a time machine?

This is one of those funny weird questions that do not have an exact answer but are interesting enough to be asked.

52. Between mind-reading or time traveling, what magical power would you choose?

Both mind reading and time traveling are both juicy powers to have. But which is more important, being able to read minds or being able to travel through time.

53. Why aren’t humans buried vertically to save more space?

Apart from cremation, a common burial practice is burying a dead person in the ground, and the dead person is buried horizontally which is thought to take up more space than burying the dead vertically/upright. This weird question is sure to create an interesting conversation.

54. What is the naughtiest thing you have done this year?

Asking a person about the naughtiest thing they have done is a very weird question. Before you go ahead to ask this question be prepared to hear naughty things and also be sure the question wouldn’t be offensive to them.

55. Would you rather be a dragon or a unicorn?

Dragons and unicorns are mythical creatures—whilst dragons are dreadful and terrifying fire-spitting beasts, unicorns on the other hand are beautiful and sought after. Asking a person this weird would you rather question, will help you find out what is more important to them; Power or Beauty?

56. If the devil punishes only bad people, why is he the bad guy?

For as old as written history, the world has read and learned of the Devil and all his atrocities. However, the devil is notoriously known for punishing evil people in the afterlife. If that is so, why is the devil branded the bad guy if he punishes bad people? This is a controversial weird question to ask the people around you. It is also fun to hear the contrasting views from the various answers.

57. Why is procrastinating bad if good things come to those who wait?

This is good food for thought. Waiting to do something later by postponing it, is procrastination. And procrastination is not seen as a good habit. But why are good things left for those who are waiting and probably procrastinating?

58. Is a tortoise that loses its shell naked or homeless?

Tortoises live in their shell and are also protected as a form of armor by their shell. So, if a tortoise should lose its shell, will it become a homeless tortoise or a naked tortoise?

59. If a brother is called bro, why isn’t a mother called mot?

This is also a funny weird question to ask the people around you. The multiple answers that this question will bring make it even funnier.

60. Since it’s your first time searching for it, why is it called research?

The English language can be quite contradictory sometimes. “Re” searching should ordinarily mean repeating a search however if you are trying to find out something for the first time to gain knowledge, it is also called research. This question will get the people around you to think.

The aforementioned 60 questions are weird and crazy enough to get your friends or people around you commending your conversation-starting skills. Asking weird questions should be fun and not awkwardly annoying. Our list of crazy and weird questions to ask your friends or people around you that we have provided is sure to give you enjoyably interesting things to talk about.

Princess is a writer and an enlightened being.


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