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99 Random Questions to Ask – Fun and unexpected questions.

99 Random Questions to Ask – Fun and unexpected questions.

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random questions - main in postWhy should everyone want to know random questions to ask?

Because, random questions work so well because they throw your audience off balance in a conversation. That often makes people give more honest and genuine answers. And because of that, they’re powerful questions to ask to know, to help keep conversations interesting.

Use some of these random questions to shock and jostle your conversation partners into really interesting talks.

 

Contents

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12 Random Conversation Starting Questions

If you want to throw out a curve ball, there’s no better place to do it than at the beginning of a conversation.

For that reason, random questions make for great conversation starters. Not sure about that? Just try a few of these.

Here are 12 random conversation starting questions:

1. If you had the world’s attention for 30 seconds, what would you say?

You’re on the clock, so make every word count.

random questions - 1. If you had the world's attention for 30 seconds, what would you say

2. If you had to work but didn’t need the money, what would you choose to do?

An interesting way to ask about the dream career.

3. What is in your fridge right now?

Wacky, but you’ll find out a lot about their diet.

4. If you were home on a rainy Sunday afternoon, what movie would you most want to see on television?

Everyone has a favorite.

5. Where do you not mind waiting?

In some places, the waiting is the best part.

6. If you could close one fast food chain, due to disgusting food, what would you pick?

A great way to get a real debate going.

random questions - 6. If you could close one fast food chain, due to disgusting food, what would you pick

7. If you could dis-invent one thing, what would it be?

What invention has caused the most misery?

8. If you could be a member of any TV-sitcom family, which would it be?

Who doesn’t want to be in a perfect TV family?

9. What would be the best thing about not having a sense of smell?

Fun and weird and makes people think.

10. Would you leave your hometown forever or stay in your hometown forever?

Is home really where the heart is?

11. When scrolling through social media, do you prefer posts from celebrities or from your best friends?

How do people get their gossip fix?

random questions - 11. When scrolling through social media, do you prefer posts from celebrities or from your best friends

12. Is there an app that you hate but use anyways?

Probably social media.

13 Random, Funny Questions to Ask

One great thing about being random, it often gets a laugh. So, one of the best ways to make sure you have funny questions to ask is to make those funny questions as random as possible.

Try these out and get more than a few surprised chuckles as well as some outright guffaws.

Here are 13 random, funny questions to ask:

13. If you could only speak one word today, what would you say?

Let them decide them make them live by it for ten minutes.

14. What is the stupidest thing you’ve done because someone dared you to?

Everyone’s got a great story.

15. What is the stupidest thing you’ve done on your own free will?

An excellent follow up to the question above.

16. If you could lock up one person in a mental institution, who would it be?

Your mother? A politician? Your boss?

random questions - 16. If you could lock up one person in a mental institution, who would it be

17. What part of your body could use a little lotion?

Oh the possible answers to this one…

18. What part of the human face is your favorite?

Gets a laugh for being random, then makes people think.

19. Do you do dance crazy when no one is looking?

Get them to show the dance.

20. What was the best thing before sliced bread?

Have fun finding out the history of sliced bread first.

21. If you could wedgie any historical figure, who would you pick?

The mental image of Hitler with a wedgie is enough to justify this question.

random questions - 21. If you could wedgie any historical figure, who would you pick

22. How come you never read about a psychic winning the lottery?

A “hey, yeah, why is that?” question.

23. How many pennies would fit into this room?

Pull out a penny and start speculating.

24. You’ve been given an elephant. You can’t get rid of it. What would you do with it?

Well, you wouldn’t need a car anymore.

25. What’s the wildest thing you’ve ever done in a hotel room?

You know, some people do more than sleep in those places.

10 Random Would You Rather Questions

Would you rather questions mix well with random questions, because you get the advantage of surprise while also getting more control because force the person to give one of two answers.

Use these to navigate your next conversation in shocking but still controlled ways.

Here are 10 random would you rather questions:

26. Would you rather be trapped in an elevator full of men with BO or three soaked dogs?

It’s a tough call that no one wants to make.

random questions - 26. Would you rather be trapped in an elevator full of men with BO or three soaked dogs

27. Would you rather live (permanently) in a roller coaster park or in a zoo?

Pick your fun place (one you won’t get sick of).

28. Would you rather look like a potato, or feel like a potato?

What does a potato even feel like?

29. You’re in the circus, would you rather be the person with their head inside the lion’s mouths or get shot out of the cannon?

Both sound fun and crazy at the same time.

30. Would you rather never be able to express yourself accurately or always have to say the exact truth?

Random, but tells you if people would rather be honest or not.

31. Would you rather be able to copy and paste in real life, or undo in real life?

Find out if the person defines themselves by missed opportunities or mistakes.

random questions - 31. Would you rather be able to copy and paste in real life, or undo in real life

32. Would you rather keep your current sleep schedule or hibernate for 3 months and have 9 months of 24/7 alertness without being tired?

The possible positives and negatives to hibernating will keep people talking for a while.

33. Would you rather have a permanently clogged nose or a piece of green food always stuck in your teeth?

Funny sounding voice or that embarrassing smile?

34. Would you rather be able to breathe underwater or have the agility of a cat?

Everyone loves a good superhero question.

35. What makes someone a hero?

The term gets thrown around a lot, but actually defining what makes a hero is difficult.

14 Random Questions to Ask a Girl

Let’s be honest, if there’s anyone you want to have some interesting and unique conversations with, it’s probably a girl.

Having random questions to ask a girl is a great way to get her attention and to keep it because with these questions to ask a girl she’ll never know what’s coming next. Use these to get the best possible conversation out of the girl you’re talking to.

Here are 14 random questions to ask a girl:

36. If you inherited a private jet from a stranger, what would you do with it?

Find out where she would go if money and time was no object.

random questions - 36. If you inherited a private jet from a stranger, what would you do with it

37. What are you freakishly bad at?

Einstein couldn’t tie his shoelaces. What task does she fail at?

38. What’s something you’ve tried, that you’ll never, ever try again?

People often go for the obvious (and opposite) question, asking about things someone enjoyed doing.

39. What are the qualities you really enjoy in a friend?

Knowing what qualities she looks for in people will be crucial to developing any relationship.

40. In what situation or place would you feel the most out of place in?

Give her a chance to tell you where she feels uncomfortable.

41. Would you rather have unlimited sushi for life or unlimited tacos for life?

A tough choice for any food lover.

random questions - 41. Would you rather have unlimited sushi for life or unlimited tacos for life

42. What’s an ideal Christmas/holiday for you?

Few things speak to what someone wants out of life more than an ideal Christmas/holiday.

43. What’s a common thing that you think about when you’re alone?

Give her the chance to show a side of herself you don’t usually see.

44. What is the most difficult challenge thus far in your life?

The one she chooses will tell you how she sees the story of her life.

45. If you could change one thing about your upbringing, what would it be?

We are who we were raised to be, so what would she change if she could?

46. When you are old, what do you think children will ask you to tell stories about?

What events will matter in fifty years? And what will you be able to say you did during those events?

random questions - 46. When you are old, what do you think children will ask you to tell stories about

47. When things break, do you prefer to fix them or replace them?

Find out if she’s the sort of person to stick it out or to walk away.

48. What product would you seriously stockpile if you found out they weren’t going to sell it anymore?

It’s the one thing she can get on a shelf that she can’t live without.

49. Do you recycle?

How much does she care about the planet?

13 Random Questions to Ask a Guy

The right questions to ask a guy are often random questions because, let’s be honest, guys are always just a bit random, and they love to get the chance to show it.

Use some of these random questions to ask a guy next time you want to get a little closer to a guy.

Here are 13 random questions to ask a guy:

50. What’s the best on-screen bromance?

His choice will tell you what he finds most fulfilling in male relationships.

51. What is your favorite type of workout?

If he works out, he’s got an opinion on this.

random questions - 51. What is your favorite type of workout

52. If your food is bad at a restaurant, would you say something?

Does he like to take a stand or just let things go?

53. How often do you look at your phone every day?

We’re all technology obsessed, but just how obsessed is he?

54. Describe your life using one word.

It’s a challenge, but the choice will tell you a lot.

55. Have you ever cried at a movie?

Men like to pretend they don’t cry. If he admits he has, it shows he’s comfortable being sensitive.

56. Who from your past do you really wish you’d stayed in contact with?

Who’s that special someone that got away for him?

random questions - 56. Who from your past do you really wish you'd stayed in contact with

57. When you meet someone you’re attracted to, what do you first notice about them?

It says a lot about a man what he notices first.

58. Do you have tattoos?

Tattoos always bring up strong opinions one way or the other.

59. What do you think about clowns?

Love them or terrified, clowns get a response.

60. If you had all the money in the world, what would be the first thing you’d buy?

Cars, trips, season tickets to his favorite team: what’s the thing he desires most?

61. Who gives you the courage to try new things?

Is it a spiritual leader? A parent? A friend?

random questions - 61. Who gives you the courage to try new things (1)

62. Are you willing to give the shirt on your back to someone who needs it the most?

Drop this one unexpectedly to get an honest answer.

14 Random Questions to Ask Your Girlfriend

The trick to keeping a relationship strong is not getting too complacent. If you turn off your brain and forget to appreciate what you have, things can fall apart quickly.

One of the best ways to shock you and your partner into paying attention is having some questions for couples on hand.

Use some of these questions to ask your girlfriend to make sure she’s still giving you her full attention.

Here are 14 random questions to ask your girlfriend:

63. If you could run one business, which would it be, and how would you change it?

Let her imagine running her favorite company.

64. What are you most looking forward to in the next 10 years?

Does she want to be married? Have kids? Start a new career?

65. What do you wish you’d accomplished by now in life?

Where does she think she’s fallen short?

66. What’s the craziest or most out-of-character thing you’ve ever done?

Hear a great story and learn how daring she is.

random questions - 66. Whats the craziest or most out-of-character thing youve ever done

67. What are you most likely to stay up all night talking about?

Find out and then talk until the sun comes up.

68. What do you get every time you go grocery shopping?

Find out which foods she craves and which ones she eats just to stay healthy.

69. Spontaneity or stability?

Excitement or steadiness? The age old relationship question.

70. What are you most likely to become famous for?

Let her brag about herself a bit and find out what she’s most proud of.

71. What makes people perfect for each other?

Get her to describe her perfect partner to you.

random questions - 71. What makes people perfect for each other

72. Do you ever want to just walk away from technology?

With this, you’ll genuinely find out how technology-addicted she is.

73. What’s the most interesting thing you’ve seen online this week?

Politics, fashion, or gossip about friends: find out what she finds interesting.

74. What makes you smile about us?

Use this question to start a conversation about what you both like about being together.

75. What’s the best way to spend a rainy afternoon?

Get tips on how to spend your rainy afternoons together.

76. What’s one difference between us that you love?

A relationship is not just about how you’re the exact same.

random questions - 76. Whats one difference between us that you love

12 Random Questions to Ask to Get to Know Someone

As mentioned before, random questions are great for getting honest reactions. So, almost by definition, they make great get to know you questions.

Take some of these along to get a few honest takes next time you’re meeting someone new.

Here are 12 random questions to ask a to get to know someone:

77. What chore do you absolutely hate doing?

Vacuuming, dishes, trash? Which is the worst one?

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

Riding a donkey is pretty rough on the knees.

79. What sound do you love?

You could get some really interesting answers with this one.

80. If you could paint a picture of any scenery you’ve seen before, what would you paint?

A more interesting way to find out the most beautiful place they’ve been.

81. What is something you learned in the last week?

Are they always on the look out to learn more?

random questions - 81. What is something you learned in the last week

82. What was the last experience that made you a stronger person?

Let them recount they’re toughest stories.

83. What is your first memory of being really excited?

Early memories are formative. This will say a lot about the person.

84. At what age did you become an adult?

For some, it was 18, for others, 35.

85. The best part of waking up is?

It’s probably not Folger’s in your cup.

86. If you could learn any language fluently, what would it be?

You’ll find out what culture the person is really interested in.

random questions - 86. If you could learn any language fluently, what would it be

87. Do you get along with your parents?

Love ’em or fight with ’em, they’re crucial to how we see ourselves.

88. What is the one food that you would never give up?

Not just a favorite, one you can’t live without.

11 Random, Deep Questions to Ask

While a lot of the questions above are just fun, random questions can also launch some of the best deep conversations.

When you have deep questions to ask, you don’t have to always build up to them, sometimes it’s better to be random.

Catch people off guard with a little philosophy by using a few of these.

Here are 11 random, deep questions to ask:

89. If you had unlimited resources, how would you live your life?

A chance to discuss the meaning of life without having to worry about money.

90. When was the last time you took some time to be alone?

What does it mean to be alone?

91. What habits are holding you back from success?

How are you your worst enemy?

random questions - 91. What habits are holding you back from success (1)

92. What is the source of your procrastination?

A chance to confess some bad habits.

93. Who are you becoming?

Not just who you want to be become: where is your life leading?

94. Do you think any kind of afterlife exists?

About as intimate and deep a question as exists.

95. What’s your personal image of God?

If someone believes in God, that image is central to their identity.

96. What would be harder for you, to tell someone you love them or that you do not love them back?

A crushing choice.

random questions - 96. What would be harder for you, to tell someone you love them or that you do not love them back

97. When you’re 90 years old, what will matter most to you?

Another way of asking what really matters in life.

98. Do you serve money or does money serve you?

Perhaps the greatest questions in our society.

99. What do people do too much of today?

What bad habit is keeping us all back?

random questions - 99. What do people do too much of today (1)

How to Ask Random Questions: 2 Steps

Random questions are great not just because of the reaction they get but because of how simple they are to pull off. It’s really just as simple as 1-2. That’s it two steps:

1. Choose your question

Pick a question that fits the audience you’re talking to. If it’s your boss, don’t go to scandalous or absurd. If it’s your friend, pick a question that’ll get a laugh.

There’s a random question for everybody out there, but you have to make sure you’re using the right one for the right person.

2. Choose your moment

This is the crucial point. Find a time when you can spring a great question and it will be appreciated.

Make sure people are in the mood for something a bit random, and then, throw it out there and watch for great reactions.

Downloadable List of Random Questions To Ask

Here is a downloadable list of random questions to ask (right click the image and select Save Image As…):List of Random Questions To Ask

More Questions to Ask

If you’re not in the mood to be random, no worries, Mantelligence still has you covered. Just click on these articles to find all kinds of great questions:

  1. If you’re looking to make people make tough choices, use some of our this or that questions.
  2. If random isn’t weird enough for you, go get some weird questions to ask.
  3. Or, just cut straight to the point and show how intriguing you are with our interesting questions to ask.

In Conclusion

There’s a lot of charm in being random, but pulling it off requires you have the right persona and the right questions to ask.

If you’ve got the persona and the questions down, you’re set.

Then, people will learn that your randomness can be a lot of fun, and you can learn a lot about them by how they answer your questions.

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