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81 Random Questions to Ask - Fun & Great Questions You Need To Ask

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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 Dai ...
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by | September 7th, 2021


Why should everyone want to know random questions to ask that can be found in this post?

Because random things to talk about work so well. They throw your audience off-balance in a discussion, which often makes people give more honest and genuine answers.

I've written lots of blogs about questions to ask to help keep talks interesting, and these ice breaker questions can shock and jostle your talking partners into really interesting talks.

Let's start!

Contents

5 Best Random Questions That Are Great Conversation Starters

If you want to throw out a curveball, 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. No need for a random question generator. Just try a few of these.

Here are the best 5 random questions:

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

What invention has caused the most misery? What invention can we live without?

2. What do you think is your guilty pleasure?

Some people's guilty pleasures are food, some a good movie, or even dancing. There's nothing wrong with finding something that would make you happy as long as you're not hurting anyone.

3. If you were given a chance to change your career, what could be your dream job?

Everyone wanted to be an astronaut at some point. But realistically, what job would you like to take if given the chance?

4. What's your opinion on fate?

Deep questions like this open up better opportunities to get to know each other better. If topics about the cosmos and the universe can't tell you what kind of person is in front of you, I don't know what will.

5. Who do you look up to as a role model?

People often role model those whom they admire. You might be shocked to hear their answers to this, but it's refreshing to understand why your friends act this way or that, finally.

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5 Funny, Unique Questions to Ask

One excellent thing about random funny questions is that they often get laughter. 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 surprising chuckles, as well as some outright guffaws.

Here are 5 random, funny questions to ask:

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

Let them decide then make them live by it for ten minutes. Try conversing with them, but they only have to use this word and some non-verbal cues. It's bound to get hilarious!

7. What was the best thing before sliced bread?

Have fun finding out the history of sliced bread first. But the universal answer's to this funny question is Betty White. That's right, Betty White is older than sliced bread.

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

The mental image of Hitler with a wedgie is enough to justify this interesting question. Imagine Hitler getting a wedgie in his shorts. Ah, that's a sight.

9. How many pennies would fit into this room?

Pull out a penny and start speculating. Better remember your volume formulas right now. If you're in a rectangular room, try out length times width times height to find out the volume.

10. What's the wildest thing you've ever done in a hotel room?

You know, some people do more than sleep in those places. For example, some people hold pretty wild rave parties in their hotel rooms.

5 Random Would You Rather Questions You Can Ask Someone

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?

Here are 5 random would you rather questions:

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

Do you want to spend the rest of your life among animals or thrilling rides? Pick your fun place (the one you won't get sick of).

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

Copy+Paste and Undo are extremely helpful when it comes to using the computer. Find out if the person defines themselves by missed opportunities or mistakes. Do they want to undo their biggest regret?

13. Would you rather have a boring conversation or eat your least favorite food?

Boring talks can put you to sleep, while some people would rather sleep than eat their least favorite food. Can you stomach either?

14. If you could only choose one thing, would you rather read your favorite book or snack all day?

Choosing between unlimited snacks versus reading your favorite book freely for an entire day? This is a pretty tricky question, honestly speaking.

15. Would you rather have an introverted boyfriend or with a lot of sense of humor?

It's a trick question! Plenty of introverted people have a great sense of humor. It's just they prefer a small company over many people.

5 Atypical Questions To Ask A Girl

Let's be honest. If there's anyone you want to have some exciting and unique speaking sessions 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 5 atypical questions to ask a girl:

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

Does the inheritance include fuel, flight crew, insurance, and allowance? If not, the best course of action is to sell it. Owning a jet can be VERY expensive.

17. 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. It's also time for you to assess how you treat your friends.

18. 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? The environment of their childhood years? The way their parents treat them?

19. Do you recycle?

How much does your friend care about the planet? Aside from recycling, what other ways do they help the planet out?

20. What makes someone a hero?

The term "hero" gets thrown around a lot. However, actually defining what makes a hero is difficult and complex. What actions or beliefs make you a hero?

5 Casual Questions To Ask A Guy At Any Random Situation

The right questions to ask a guy are often random because 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 5 questions to ask a guy:

21. Have you ever cried at a movie?

Men like to pretend they don't cry, and it's the strangest thing for a girl. If he admits he has, it shows he's comfortable being sensitive.

22. Who from your past do you really wish you'd stayed in contact with?

Bonds are important when it comes to friendship so is communication. Who's that special someone that got away for him?

23. 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, a woman as well. What attractive traits do you notice first?

24. Do you have tattoos?

Tattoos always bring up strong opinions one way or the other. Also, some tattoos have deep meanings, so it's a pretty good deep discussion opener.

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

Cars, trips, tickets to his favorite sport? His favorite thing: what's the thing he desires most? What would he buy?

5 Questions To Ask Your Girlfriend That Are So Random

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.

And knowing the best things to talk about with your girlfriend can make your relationship stronger. Use some of these questions to ask your girlfriend to make sure she's still giving you her full attention.

Here are 5 questions to ask your girlfriend:

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

Does she want to be married? Have kids? Start a new career? Does she want to own a successful business? Does she wish to live away from society?

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

Hear a great story and learn how daring she is. If she hasn't done anything, both of you can plan a daring adventure. It's a good thing to look forward to.

28. 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. Remember what food to bring her to make her happy.

29. 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. Does she want to become famous for her delicious homecooked meals or her fantastic dance skills?

30. What makes you smile about us?

Use this good question to start a conversation about what you both like about being together. You might even find yourselves adorably smiling from ear to ear.

5 Random Questions 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 random questions to get to know someone along to get a few honest take-ups next time you're meeting someone new.

Here are 5 random questions to ask to get to know someone:

31. What chore do you absolutely hate doing?

This is a fun question. Vacuuming, dishes, trash? Which is the worst task to do in the house?

32. 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. Also, ask them to describe the place in detail so that you'll get the idea.

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

Early memories are formative. Sometimes, childhood memories shape the way people look at life as adults. This conversation starter will say a lot about the person.

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

You'll find out what culture the person is really interested in. Perhaps, you'll even learn a new thing about this culture.

35. Do you get along with your parents?

Love 'em or fight with 'em. They're crucial to how we see ourselves and important in our upbringing.

5 Random But Deep Questions to Ask

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

Deep conversation topics involve questions to get to know someone deeply. When you have deep questions to ask, you don't have to build up to them constantly. Sometimes it's better to be random.

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

Here are 5 random, deep questions to ask:

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

This is the chance to discuss the meaning of life without having to worry about money. What would you really want to do?

37. What habits are holding you back from success?

How are you your worst enemy when it comes to your success? Would you like to redo some things?

38. What's your personal image of God?

There are a lot of ways that people envision God. If someone believes in God, that image is central to their identity and life.

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

Another way of asking what really matters in life. Does family matter most? Money? Friendship? Love life?

40. What do people do too much of today?

What bad habit is keeping us all back? What do you wish people do less? Why this activity?

5 Quirky 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? Relationship questions can definitely do the job. Conversation starters for couples should involve some questions for couples, obviously!

Here are 5 quirky questions for couples: 

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

Some people do, and some people don't. Do you believe that men and women can have platonic friendships?

42. What's one thing no one knows about you?

This question requires absolute honesty. But of course, you should still give them the privacy they need if they do not wish to answer.

43. What ran on your mind on our first kiss?

This is such a great question to ask. You can be nostalgic about your first kiss and share a smile on the memory.

44. With who did you made your last phone call?

What was the call for? How long did you talk to them? Do you call this person often?

45. What is your all-time favorite song?

Get to know their music taste better. What about this song makes them feel happy?

6 Random At The Same Time Weird Questions To Ask

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

Here are 6 random and weird questions: 

46. Hero or villain for a day?

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

47. Which way should toilet paper hang, over or under?

We all know the answer to this one. Toilet paper is actually made to hang up or over. It's even patented.

48. Pineapple or Anchovies on pizza?

If these two are the only options, please say "Neither." Just kidding! What's their taste on pizza?

49. Green or red grapes?

What's the difference even? Crunch? Color? Taste? Do you prefer one over the other?

50. Bathroom singer or dance in the shower?

Dancing in the shower is a dangerous sport. So if they're more of a dancer, tell them to be careful when they unleash their skills in the shower.

5 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 5 random never have I ever questions: 

51. Never have I ever imagine myself as one of the main actors fighting in a zombie apocalypse.

Alright, this is a random yet very specific inquiry. However, paired with creative imagination, you can further the conversation into a full-blown story writing session.

52. Never have I ever been banned in a public place.

This is such a fun topic. If you or the other person has been banned from going somewhere, make sure that you spill the details.

53. Never have I ever stalked my ex.

C'mon, everyone has already stalked their ex on social media at one point. It's nice to be updated sometimes, especially because they've been a part of your life.

54. Never have I ever chose someone over my best friend.

Choosing other people over your best friends can happen. But best friends will always be there, no matter what.

55. Never have I ever faced my biggest fear.

Now's the time to learn about what they fear most. You can end up having a deep talk because of this one.

5 Unusual 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 5 truth or dare questions: 

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

The answer to this one can be both hilarious and genuinely impressive. It's exciting to know how many pancakes one person can eat in one sitting.

57. What's the craziest thing you did as a kid?

Kids are ultra-hyper and creative and always do the weirdest thing. Get ready for a possibly weird tale following the answer to this one.

58. Who would you want to be with on a desert island?

Some people would say some famous TV character. But realistically, you'd want to be someone who's resourceful.

59. What's the most embarrassing thing you have ever done?

There are plenty of things that we're embarrassed to have ever done. Why not share some of them and get laughs in return?

60. If you could have a superpower of a fictional character, what would it be?

This one may need some thinking. What superpower would you really want to have? Be it flight, invisibility, invincibility, or control of the weather, all of these superpowers are cool.

5 Random First Date Questions That'll Help You Keep The Conversation Going

If you are sick of asking the same first date questions, having some funny random questions at your disposal will help you make the date exciting. Never run out of things to talk about on a first date with these first date conversation starters.

Here are 5 random first date questions: 

61. 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. Ask them what they like about this place?

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

Gratitude is an excellent way of reflecting on life. So why not ask this question on your first date? You'll see if they revel in the little things.

63. Do you think FRIENDS is a bad TV show?

This is the ultimate controversial question. Although there are some jokes on there that didn't age well, it's an entertaining show, nonetheless.

64. What is your favorite movie you could watch all over again?

If you could watch a movie for the first time all over again, which would you pick? A drama? Action movie? Or a series of movies?

65. If you could only eat one food for the rest of your life, what would you choose?

This is such an adorable topic when you're on your first date. You can even use the answer here on your second date.

5 Random Yet 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.    Interesting things to talk about and interesting conversation topics can bring out important information about the person you want to know more.

Here are 5 random yet interesting questions: 

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

The answer to this one can be really insightful and inspiring. Also, it's in connection with the upbringing subject.

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

This is a really deep question. It makes you think. But it's always a good one to ask.

68. Who was your first celebrity crush?

Everyone has a celebrity crush. Remember the moment you saw this famous person on TV or on the big screen?

69. What is the best candy flavor?

Are you a sweets connoisseur? What candy is always at the top of your list? Chocolates? Hard candy? Gummy bears?

70. What's the largest amount of money you've had to borrow off of a friend or family member?

This might be a touchy subject for some people. But it's interesting for small talk, nonetheless. It gives you an idea of their generosity.

5 Random Questions That Are Also Personal To Ask

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

Here are 5 random personal questions: 

71. 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?

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

When you ask someone this personal question- what they think are their best and worst personality traits, you will be surprised at their answer. Get ready.

73. What's your favorite hobby?

Some people are lucky enough to have spare time to enjoy their favorite hobbies. What's yours? What activities do you enjoy?

74. Where is your dream vacation?

It's your chance to know the only place in the world they'd go on a vacation if given the chance. Maybe you can set an actual trip there on your favorite holiday.

75. What is your secret talent?

Avoid any awkward silence with this topic. Are you secretly a singer? Can you rap the entirety of "Rap God" with ease? Can you play an instrument?

5 Random Questions To Get To Know Your New Friend Better

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 5 random questions to ask a new friend: 

76. What takes up too much of your time?

There are just some things in life that we put too much unnecessary time into. Only a minority of these activities are really worth the time and effort.

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

You can both proceed to interpret the dream. Maybe it means something? Does the dream still haunt you today?

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

Perhaps this movie reminds them of someone special. Give it a watch. You might cry, too.

79. What’s the funniest name you can think of a pet?

Pets deserve the best name because they're the best. But naming a dog "Porkchop" or "Chicken" is the funniest thing.

80. What’s the worst thing you ate from a restaurant?

What restaurant would you give zero stars? Rant out your experience with your newfound friend.

81. What was the most interesting thing you have seen lately on social media?

There's always something new on social media that might pique your interest. Be careful about what you believe though.

Downloadable and Printable List of Random Questions To Ask

Here is a downloadable and printable jpg/pdf list of Random Questions To Ask (right click the image and select Save Image As...):

Frequently Asked Questions

More than just asking the usual questions like "What's your favorite color? Favorite restaurant? Favorite sports team?", create any great conversation with anyone. We'll help you with that.

What can I text randomly to a girl to make her day?

Random messages can make anyone's day. If you want to text the girl you like out of the blue, send her something that reminded you of her- a song, perhaps. Like this: "Do you know The Maccabees' song, Toothpaste Kisses? I don't know why, but it reminds me of you."

How do I keep our conversation interesting?

Any conversation can be made more interesting by asking interesting questions. Make sure that you use the ones on our list.

How to use good random questions to have a meaningful conversation?

It's the way that you ask follow-up questions. Ask ones that need a long answer and just go from there.

What random topics should I discuss with the girl I like?

These random topics or icebreaker questions should be interesting for her. For example, if she likes talking about the stars, go for topics surrounding them.

What should I say to get a girl's attention?

Sometimes, it's not about what you say but how you act when you're with her. Try an insightful topic. You can also ask about her biggest pet peeve to get her riled up.

How to Ask Questions Randomly

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 one that fits the audience you're talking to. If it's your boss, don't go too 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.

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 you want to know how to get your Valentine's date on another level, here are some Valentine's day questions to ask.
  3. Are you up for a challenge? Try these unanswerable questions with your peers.

In Conclusion

There's a lot of charm in being random, but pulling ice breaker questions 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 some random things to talk about can be a lot of fun, and you can learn a lot about them by how they answer your questions.

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