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122 Random Questions to Ask – Fun and unexpected questions.

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Why 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

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.

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.

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?

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?

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.

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.

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.

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.

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.

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.

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.

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?

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?

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.

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.

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.

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 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?

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.

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?

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.

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?

3 random questions for couples

As a couple, you probably know everything you need to know about each other. But what if you want to know that little bit more? Ask some questions for couples obviously!

Here are 3 random questions for couples: 

100. If you could trade lives with someone, who would it be?

The Dalai Lama? Beyoncé? Emma Stone? The possibilities are endless.

101. Do you believe it’s possible to maintain platonic friendships with members of the opposite sex?

Some people do and some people don’t. Which one are you?

102. What’s one thing no one knows about you?

This question requires absolute honesty.

3 random weird questions

When the conversation takes a nosedive, you need to ask some weird questions in a fast fire round.

Here are 3 random weird questions: 

103. Hero or villain for a day?

Depending on the repercussions, you will be surprised by how many people want to be a villain.

104. Is never returning something you borrowed considered stealing?

There is a fine line here but it changes from person to person.

105. Have you ever dropped food on the floor and then picked it up and eat it?

If someone answers no to this question, they are definitely lying!

3 random never have i ever questions

Never have I ever questions can get a little bit boring but when you have random questions up your sleeve, the answers are sure to be hilarious.

Here are 3 random never have I ever questions: 

106. Never have I ever hidden cigarettes so my parents wouldn’t know I was smoking.

Everyone was a teenager at some stage in their lives, so it stands to reason that a lot of people have done this.

107. Never have I ever been fooling around in a car and accidentally honked the horn.

A little bit naughty and very funny, this is one of the best never have I ever questions to ask.

108. Never gave I ever been electrocuted.

This question always comes with some hilarious answers.

3 random truth or dare questions

Do you want to make a conversation really exciting? Then make sure you ask some truth or dare questions! You never know what might happen.

Here are 3 random truth or dare questions: 

109. If you could create your own job title, what would it be?

It’s amazing the type of job someone will make up.

110. How many pancakes have you eaten in a single sitting?

The answer to this question can be both hilarious and genuinely impressive.

111. Do you lick your plate?

If it was socially acceptable to do so? Always.

3 random first date questions

If you are sick of asking the same first date questions, having some funny random questions as your disposal will help you make the date exciting.

Here are 3 random first date questions: 

112. Do you have a special place you like to visit regularly?

Whether it’s to clear your head or to have fun, everyone has their favorite place.

113. What is the reason you are most grateful in your life?

Gratitude is a great way of reflecting on life. So why not ask this question?

114. Do you think Friends is a bad TV show?

This is the ultimate controversial question.

3 random interesting questions

When you’re getting to know someone, sometimes the devil is in the details. That’s why you need to ask some more interesting questions.

Here are 3 random interesting questions: 

115. Favorite day of the week?

Spoiler: It’s never Monday.

116. What life lessons would you pass on to your children?

The answer to this question can be really insightful and inspiring.

117. Do you feel like the good time outweigh the bad?

This is a really deep question, but it’s always a good one to ask.

5 random personal questions

The same old questions can get a little boring. But with some carefully picked random personal questions, you can make the conversation both informative and fun, all at the same time.

Here are 5 random personal questions: 

118. Who or what inspires you to be a better person?

We beat that if someone is always a little inspired, it’s because they are inspired by someone amazing.

119. What time do you normally go to bed?

They say that having a good sleep routine is important but let’s face it, who really goes to bed on time?

120. What is the best and worst part of your personality?

When you ask someone what they think are their best and worst qualities, you will be surprised at their answer.

121. What spells fun for you?

If they answer F-U-N, it probably best to ask another question.

122. Do you believe in Bigfoot?

The world is divided into two types of people. Those who believe and those who don’t.

random questions to ask a new friend

When you’re thinking of questions to ask a new friend, it can be easy to get pressured because you want to make sure to ask them the right questions. Don’t get caught up in thinking of questions and just let it go. The more random the questions, the more fun you can have.

Here are 9 random questions to ask a new friend: 

123. What takes up too much of your time?

There are just some things in life that we put too much unnecessary time into.

124. What’s your favorite part of the day?

So that you know when it’s best to ring your new friend up.

125. Do you find clowns creepy?

Is their target market really kids?

126. What’s the longest time you had to wait for something?

Sometimes, waiting so long for something is really just worth it.

127. What do you do when no one is around?

The things we do in secret are definitely a thing to be talked about.

128. Do you sometimes talk to yourself?

The best conversations are those that we have with ourselves.

129. What’s the scariest dream you’ve ever had?

You can both proceed to interpret the dream. Maybe it means something?

130. What’s the most ticklish spot on your body?

Word of Advice: Don’t tickle them there.

131. What’s the first movie that made you cry?

Give it a watch. You might cry, too.

How to Ask Random Questions

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.

Here is how to ask random questions:

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 and Printable List of Random Questions To Ask

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

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.

About The Author

Jasper

Jasper is our expert conversationalist and wordsmith. He loves coming up with questions, jokes, and topics designed to create natural conversation. His work has been featured on Marriage.com, iHeart Media, Elite Daily, and The Urban List. Jasper lives in Georgia with his new bride.

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