82 Weird Questions to Ask – Spark conversations with creativity.

Alright, don’t be weird about this… because having weird questions to ask someone could be the difference between a good conversation and a bad one.

Did you know that some people put their milk in the bowl before their cereal? That sometimes people wear socks with sandals? There are people out there who fill their bathtub up halfway, block the drain, then turn on the shower and pretend they’re in a sinking submarine. 

We’re all weird in our own ways. Those weird things we do are what make us who we are. And if you want people to like you, you have to embrace your weirdness and simply be yourself no matter who’s watching.

When you try to be someone else, people (especially women) see directly through your fake personality and recognize you’re not being genuine. How can they trust you if you’re pretending to be someone you’re not? Nobody likes fake people.

So when you’re in a conversation and you run out of questions to ask, embrace your weird side and get creative with weird questions to ask.

Asking weird questions shows that you’re creative and don’t mind being silly. That you can be yourself and be confident about it. People will respond and they’ll like you more.

One important note before you begin: Being random is NOT the same as being weird. Being random is what you do with your best friend. You know each other extremely well and understand each others’ humor so it’s understood that you’re going to be ridiculous together with your inside jokes and silly antics. Being random with a stranger or a person you want to like you is annoying. If you want to make friends, randomness is your enemy.

For example, simply asking “Container?” is random and allows for no reasonable answer. On the other hand, asking a person, “What’s your favorite container?” is random, yes, but it also offers them to think about a special keepsake box, a piggy bank from their childhood, or some other . This is what I mean when I talk about being random. As long as you offer a chance for a reasonable response, you can engage in a meaningful conversation.

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9 Best Weird Questions to Ask

Weird questions are unique in a way. Since they tend to be so outlandish, they offer a new way of looking at things which in turn brings more thoughtful responses to the questions asked. They’re fun and can turn a boring conversation into a more interesting exchange.

Here are 9 best weird questions to ask:

1. Who is the fourth person on your missed calls?

Does the number start with the first three numbers of your phone number? It’s a popular scam these days.

2. What shirt are you wearing?

As weird as this sounds, the shirt might have a story behind it.

3. Warm lighting or bright white lighting?

Soft, tan-colored lighting for relaxing or brighter faux-sunlight for staying awake?

4. What’s a saying you say a lot?

‘Mkay, this could or could not be the same as those ticks your teachers have, ‘mkay?

5. You discover a beautiful island upon which you may build your own society. You make the rules. What is the first rule you put into place?

This one is out there but it’s also fun!

6. You have been given the opportunity to create the half-hour TV show of your own design. What is it called and what’s the premise?

You’re the producer, the writer, the director. Make it great!

7. One night you wake up because you heard a noise. You turn on the light to find that you are surrounded by MUMMIES. The mummies aren’t really doing anything, they’re just standing around your bed. What do you do?

Spooky!

8. The Angel Of Death has descended upon you. Fortunately, the Angel Of Death is pretty cool and in a good mood, and it offers you a half-hour to do whatever you want before you bite it. What are you gonna do in that half-hour?

What would you do with only a half hour to live? Would your decision end up being your demise?

9. The Celestial Gates Of Beyond have opened, much to your surprise because you didn’t think such a thing existed. Death appears. As it turns out, Death is actually a pretty cool entity, and happens to be in a fantastic mood. Death offers to return the friend/family-member/person/etc. of your choice to the living world. Who will you bring back?

Would it be someone close to you or someone famous who might bring some more happiness to the world? What would the implications be if it was a famous person? How would things change if society realized the God of Death was the one, true God?

6 Funny, Weird Questions to Ask

People love to laugh and they really like people who make them laugh. So when you run out of funny questions to ask, get goofy with these 6 funny, weird questions to ask! You’ll undoubtedly have a good time.

Here are 6 funny, weird questions to ask:

10. You can flip a switch that will wipe any band or musical artist off the earth?

Which band is the bane of your existence?

11. Who would you really like to just punch in the face?

We all have someone.

12. You accidentally ate some radioactive vegetables. They were good, and what’s even cooler is that they endow you with the super-power of your choice! What’s it gonna be?

Instead of asking, “What superpower would you choose?”, adding a little flair to a question is effective.

13. The constant absorption of magical moonbeams mixed with the radioactive vegetables you consumed earlier have given you the ability to resurrect the dead famous-person of your choice. So which late celebrity will you bring back to life?

See? It’s a weird way of asking a normal question.

14. Name the top five things to take with you during a zombie outbreak.

Who hasn’t thought of this?

15. How would you quickly dispose of a dead body in a hotel room?

Are you asking for a friend?

5 Weird Ice Breaker Questions

You’ll love our curated list of ice breaker questions to keep you on your toes. These ice breaker games are sure to get some laughs or invite deep thinking and greater intimacy and compassion.

Here are 5 weird ice breaker questions:

16. What’s the toughest decision you ever made?

Often something gained comes at huge sacrifice.

17. What have you forgotten?

Put some good old pressure on them to remember on the spot.

18. How many times a day do you look in the mirror?

Are they admiring themselves or combing over their insecurities obsessively?

19. What do you bring most to a friendship?

You’ll know quickly whether they are capable of your quality level of friendship by what you answer. You’ll also see if they’re able to give themselves enough credit. Are they afraid to ask for what they need or do they see their job as giving and giving and giving in relationships?

20. What makes you feel supported?

This is a beautiful question to ask. A relationship can be so tremendously enhanced when both members feel permission to name and ask for what they need to feel supported and believe that they deserve to be so.

8 Weird Questions to Ask a Girl

Thinking of questions to ask a girl can be tough. Remember: we’re all weird in our own ways so ask the following 8 weird questions to ask a girl and she might like your quirks.

Here 8 weird questions to ask a girl:

21. If you were a student at Hogwarts, which teacher would you rather have from the choices given?

J.K. Rowling built a wonderfully magical world with countless interesting characters. If you haven’t read the books, you’re missing out.

22. Do you like someone?

Maybe she’ll tell you she likes you.

23. Tomorrow you have a date with someone in this room. Who would be the worst choice?

Especially fun to ask in a public place.

24. What would be much better if you could just change the color of it?

A food? A piece of furniture in the room?

25. When was the last time you screamed at the top of your lungs?

Why not do it now?

26. What would your dream bathroom look like?

What’s the most ideal bathroom to put things down on paper?

27. Did you ever have a crush on your best friend’s boyfriends?

Why does she get to be so lucky?

28. When was the last time you literally stopped to smell flowers?

If it’s been a while, consider going to a park or the local conservatory. We have date ideas!

8 Weird Questions to Ask a Guy

Men and women have different ways of conversing. It’s a well-known fact that men aren’t as keen talking about their feelings as women. When guys who are strangers talk to each other, the conversation generally steers toward hobbies. Nothing wrong with that.

But a man should be able to talk about anything with anyone. 

Maybe one of your female friends has a new boyfriend and she wants to know what you think of him. You’ll have to get crafty to get the information you need so try our questions to ask a guy article for some inspiration.

If those aren’t what you’re looking for, the following 8 weird questions to ask a guy will help you find out if he has a strange side and isn’t afraid to embrace it. If he can answer these without being standoffish about it, he’s probably a cool guy and your friend picked a good one. Who knows? Maybe you’ve made a new friend or learned a few things yourself!

Here are 8 weird questions to ask a guy:

29. What is your favorite form of exercise?

The best exercise is one you do regularly. Control that sweat!

30. How did you learn what it meant to be a man?

Some inspiration for those of you struggling with this.

31. If you could add a single option to your car, what would you add?

Body kit, neon, Nitrous?

32. If you were called on to be a government spy, where would you least like to serve? Where would you most like to serve?

What young boy hasn’t dreamed of being a spy in a far-away land?

33. What historical figure would you like to have a chat with?

Every man should have a historical idol.

34. Is there anything hanging in your room that motivates you?

Words that help you conquer the day are essential to success.

35. Do you find pets friendlier than humans?

Our dogs are a manifestation of our own personalities.

36. Which is one that show you cannot watch with anyone?

Some shows require a quiet room with no commentary to fully enjoy.

9 Weird Questions to Ask to Get to Know Someone

Getting to know someone can be tough especially if you can’t figure out what to talk about. Asking someone about themselves is the best way to achieve your goal but what if you don’t know what to ask?

We have a list of get to know you questions that will get you started but if you want to be quirky, try out these 9 weird questions to ask to get to know someone and show your strange side.

Here are 9 weird questions to ask to get to know someone:

37. What’s your least favorite mode of transportation?

The things a person dislikes are just as important as the things they like!

38. What songs are included on the soundtrack to your life?

Music is a fantastic way to connect with someone.

39. Which thoughts bring you a wave of relaxation?

For me, thinking about an empty office on the weekend is extremely relaxing.

40. What is your favorite combination of colors?

Black and yellow? Red and black? Alabaster and azure?

41. Which one fashion accessory do you like better than others?

Jewelry, beanies, backpacks. Get specific and tell a story of your favorite piece of fashion.

42. A man walks up to you and says he’s going to transform you into the animal of your choice and there’s nothing you can do about it. Which animal do you choose?

Another instance of adding a little flair to a simple question.

43. Which day do you think the start of the week is, Sunday or Monday?

If the beginning of the week is Sunday, your week is almost halfway over by Tuesday!

44. You have seven dollars and five minutes at the grocery store. What do you buy?

Did you know that there are ways to show you’re single while shopping?

45. If you could explore anything Indiana Jones/Lara Croft style, where would you go first?

Exploring ancient ruins while being pursued by bad guys would be an interesting way to live.

8 Weird, Deep Questions to Ask

Deep questions to ask are perfect for figuring out how a person’s brain operates. These 8 weird, deep questions to ask someone will make your conversational partner think, “That’s a weird question…” but they’ll answer it nonetheless and you’ll have a deeper understanding of what’s going on in that brain of theirs.

Here are 8 weird, deep questions to ask:

46. Why do people expect a universe full of randomness to be fair?

Freak accidents and lottery numbers can change a life but that doesn’t mean it’s fair.

47. Will humans spread out among the stars or just be a brief blip in Earth’s history?

Will the human race destroy itself or discover a way to chart the galaxy?

48. Tomorrow is the end of humanity. What destroys us?

Are we looking at a Day After Tomorrow scenario, nuclear winter, or something else?

49. Are you happy with the person you are becoming?

If not, there’s a few ways to change yourself for the better.

50. Can insanity bring about more creativity?

Cutting your ear off won’t lead to immediate results but the underlying causes might.

51. If you try to fail, and succeed, which have you done?

This one is a little mind-bending.

52. At what point are we good enough?

Or should we always strive for more?

53. Can you describe your life with a six word sentence?

It’s easier than you might think.

15 Weird Never Have I Ever Questions

Let’s be honest, never have I ever questions should always be a bit weird. It’s kind of a weird way to get some crazy information out of people.

However, there’s a major difference between your standard, unexpected never have I ever questions and the ones we’ve got here. These questions don’t just take people by surprise, they take answers in really weird directions.

Here are 15 weird never have I ever questions:

54. Never have I ever danced in the rain?

Sure to bring up some weird, happy stories.

55. Never have I ever wondered who or what I was in my past life?

Then, it’s time to consider now.

56. Never have I ever seen my doppelganger?

Hopefully, they’ve got a picture!

57. Never have I ever sleepwalked?

This always leads to great sleepwalking stories.

58. Never have I ever wondered if I would go to heaven or hell when I die?

See who’s really diehard committed to no afterlife.

59. Never have I ever killed a spider?

Do they, like, live in a place with no spiders?

60. Never have I ever searched the trash bin looking for something I accidentally threw away?

We’ve all been there, but what made someone dive into that dumpster?

61. Never have I ever wondered if I would die if I swallowed a gum?

If they hadn’t thought of it before…they are starting to now.

62. Never have I ever worried that a tree would grow inside my belly after swallowing a seed?

A great never have I ever during watermelon season.

63. Never have I ever ate a lot after a jog?

I thought that was the whole point of exercise…

64. Never have I ever had a bad haircut?

Pictures or it didn’t happen.

65. Never have I ever received a traffic violation?

Now you know who the designated driver should be!

66. Never have I ever pretended I had a phone call to get out of talking with someone?

What’s that? Sorry, can’t answer this one. Important person on the line…

67. Never have I ever sat in the back of a police car?

The stories here always make it worth asking.

15 Weird Most Likely To Questions

The charm of most likely to questions is two-fold. One, you get to play psychic and predict the future for your friends. And two, you find out what people think of one another’s prospects in life.

However, a lot of most likely to questions are pretty basic. You probably know who’s going to get a good job or move far away most of the time. But what about some weird, crazy stuff people might experience? Who’s most likely to have those adventures?

Here are 15 weird most likely to questions:

68. Who is most likely to be rich?

Find out now and be sure never to lose contact.

69. Who is most likely to give all their money to charity?

Who usually covers everyone bill? It’s that person.

70. Who is most likely to marry a celebrity?

Or, who’s got the looks, charm, and bank account to pull that off?

71. Who is most likely to hold their breath the longest as it possible?

Pick out the ones who are the best swimmers. It’s going to be them.

72. Who is most likely to die of something stupid?

Pick out the person who will never grow out of their stupidity.

73. Who is most likely to meet a ghost?

Good to find this out now and then avoid them when entering old, abandoned mansions.

74. Who is most likely to go hiking with strangers?

Probably the same one who will die of something stupid.

75. Who is most likely to go on a space mission?

If we screw up the planet royally, be sure to keep this person’s number handy.

76. Who is most likely to fall asleep during a movie?

Either who is the most overworked or the least interested in film.

77. Who is most likely to fall in love with a stripper?

Maybe the guy who failed to marry the celebrity.

78. Who is most likely to eat a bug? 

Who has the craziest palette?

79. Who is most likely to become addicted to dairy?

Find the cheese fiend in your midst.

80. Who is most likely to have a disease named after them?

That’s either a huge compliment…or a huge insult.

81. Who is most likely to open a present before the prescribed date?

Find out, then be sure never to let them near gifts early.

82. Who is most likely to help a thief escape?

Kind hearted, or were they just the easiest to buy off?

How to Ask Weird Questions

1. Let go of your pride. 

When you think you’re too cool to be silly, you’re boring and if you want an interesting conversation, you can’t be boring.

2. Preface the questions (or don’t). 

Some people aren’t comfortable with their weirdness. If they seem a little uptight, ask if they want to trade weird questions and see who can ask the weirdest one. If the person you’re already talking to seems a little out there, ask away to get on his/her level.

3. Pay Attention.

Being too weird throws people off. Be attentive to how your questions are received and tone it down to ensure the conversation doesn’t go awry.

Downloadable List of Weird Questions To Ask

Here is a downloadable list of weird questions to ask (right click the image and select Save Image As…):

More Great Questions to Ask

Looking for more great questions to ask? We’ve got you covered:

1. Would you Rather Questions are always a blast to ask and are perfect at getting a group of strangers to open up. You’ll be the life of any party if you use them.
2. If the conversation is dwindling and you seem to be losing a person’s interest, try some random questions. You might bring the conversation back from the brink of failing.
3. Get to Know You Questions are a must to get to know someone!

In Conclusion

So there you have it. A bunch of weird questions to make any conversation take a turn for the bizarre. Have fun, let your weird colors fly and be sure to have some backup questions to ask!