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, often making 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!


Best Random Questions To Ask

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

Why It's Great: Finding out which invention is the least popular among your friends can lead to an intriguing discussion. You can start by discussing what life would be like without that technology. Can you imagine how difficult it would be without cell phones today?

When to Ask It: Random questions to ask are great when you want to draw your friend's attention. If you notice everyone staring at their phones, use this to start conversations that might turn into a fun debate with your friends.

2. If you opened a business, what kind of business would it be?

Why It's Great: Asking your friends about their dream business is a great way to learn more about their passions!

When to Ask It: While this is perfect for throwing out in regular conversations, you should ask this one of your more ambitious friends. It can start a pretty in-depth discussion about money and business.

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

Why It's Great: Boring conversations can put you to sleep. But then again, some people would rather sleep than eat their least favorite meal. Both punishments are harsh, but the subject makes for a fun and intriguing discussion. Make sure to ask your friends why they made their choice.

When to Ask It: Questions like these are ironically great. Talking about boredom eases boredom. Talking about your least favorite things to eat could also make you hungry. Crazy, huh?

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

Why It's Great: It's interesting to discover what people first notice about someone, as it can reveal much about them. You can then ask your friends how they felt when they first met you. What did they find was your most attractive feature?

When to Ask It: You can bring this up when discussing dating preferences or asking random questions about attraction.

5. What would you do with 10 million dollars?

Why It's Great: No argument; it's a life changer. You'll hear all about the wacky things your friends have in store if they get that kind of ludicrous money. Would they try to own their favorite brand? Perhaps they might buy into a business. Or would they relax on some deserted island?
When to Ask It: This is another good random question you can throw out almost any time of day. We've all dreamed about winning the lottery, so many people will be able to answer this instantly.

6. What ran through your mind during your first kiss?

Why It's Great: You can ask a significant other about their first kiss. Was it with you? Either way, it's a great way to bask in the nostalgia of first loves and first moves.

When to Ask It: Use this as a conversation starter with a long-term partner. You can even bring it up when you're talking about your earlier years with your friends.

7. Never have I ever stalked my ex.

Why It's Great: In this modern age, almost everyone has looked in on their exes, even just online. Seeing them spend their favorite holiday without you on social media could be upsetting, though. Or, maybe nice?

When to Ask It: Games like "Never Have I Ever" are a great way to learn more about your friends and keep things interesting. Ask this one in a group setting or even when you're just conversing with someone one-on-one. 

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

Why It's Great: "Friends" is a beloved show many have watched. There might be people who would say that it's not that special, though. What do you think?

When to Ask It: This is a great topic to throw in when talking about things that you like. Or when talking about TV or movies. You can also ask them about their favorite season of the show.

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

Why It's Great: This conversation starter can reveal much about someone. They might share memories from when they were a child or perhaps when they were in high school. When I asked my friends, they answered prom night, and we had a great talk walking down memory lane. We had lots of laughs about things we used to lose our minds over!

When to Ask It: Ask when everyone's reminiscing or when the topic is about childhood stories.

10. What do you think is your guilty pleasure?

Why It's Great: A guilty pleasure can be anything. Some of your friends might even think your guilty pleasure is entirely innocent, while others might find it shocking. You might be surprised that your friend enjoys something you consider to be the weirdest thing.

When to Ask It: Conversations get going with questions like these. They can also strengthen your friendship. If you want to get closer to someone, try asking more personal questions like this.

11. What do you wish your phone could do?

Why It's Great: Your phone can do many new tricks. Unfortunately, apps can do only so much and some ideas haven't been invented yet. Your friends might have unique ideas that they wish their phones could do. This one will entice a creative exchange.

When to Ask It:When conversations fall flat. Another great time is when everyone is looking at their phones. Bring this topic up.

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

Why It's Great: This is unique and hilarious. Picture any historical figure, good or bad, and picture them getting a wedgie. The possibilities are endless, and this strikes for some of the most random and funny conversations.

When to Ask It: You can ask this whenever you want to be whimsical, fun, and lighthearted. After all, could this be any more random?

13. What’s your favorite number? Why?

Why It's Great: Funny enough, numbers have held significant cultural and psychological importance for some people. There are various superstitions and beliefs surrounding them. Like the number 13 being considered unlucky. Who knows, your friends might even have a unique story about that number!

When to Ask It: This one is tame, so ask away. What number makes your friend's life luckier?

14. Which is more important, having a great car or a great house? Why?

Why It's Great: Whether you're a car lover or house décor enthusiast, investing in one of these is an important thing. You'll have long discussions about this topic because there are so many things to consider. 

When to Ask It: There are many random questions to ask. But ones like these are important in life because they prompt us to reflect on our values and priorities. They provide insights into what matters to us about comfort, lifestyle, and personal satisfaction. 

15. Do you care about reviews?

Why It's Great: It's funny to learn that some people value strangers' opinions on the internet. If you ask this, you can find out if your friends are one of those people. 

When to Ask It: You can use this when discussing anything currently trending on social media or if there is something new to see. Ask if you want to learn whether reviews will influence your friend's opinion.

16. How many pennies would fit in this room?

Why It's Great: Thinking of a sudden puzzle is a great way to get everyone into deep thought. It's always funny to see how people justify their solution, even if it's wrong.

When to Ask It: When you find yourself bored with your buddies in an unexpected location. Make sure it's in an enclosed space or room so it makes sense.

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

Why It's Great: We all know what goes on in hotel rooms, or do we? Some people do more than sleep. It might surprise you what your friends have done in their hotel rooms. Why not find out?

When to Ask It: Wild vacation stories are some of the most fascinating tales to hear. Ask this when someone has just returned from a vacation and discover all the wild things they have been up to.

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

Why It's Great: Both experiences are engaging in their own right. Roller coaster parks are thrilling, but a zoo has many creatures (possibly your favorite animal) that you can always watch. The choice is yours, and this makes for a good bonding session!

When to Ask It: This is always fun to ask almost anyone. Feel free to use it whenever you like, whether it's a one-on-one convo you're having or in a group.

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

Why It's Great: It's a fun one! These unique superpowers have significant repercussions. It would be hard to choose one over the other. So make sure to ask your friends why they think having one or the other is better. 

When to Ask It: This is best left when your conversations have become stagnant. Use this when you want to make things more interesting.

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

Why It's Great: Everyone had an idea of what they wanted to do in life, but not everyone had the chance to chase it. Life is funny like that. So, ask this to learn where their true interests lie. It might surprise you that your writer friend wanted to be a doctor!

When to Ask It: If you want your friends to open up more about themselves, that's when you use this. I got to ask a family member and they surprised me when they told me they would've been a theatre actor instead of an office manager.

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

Why It's Great: It's a hard decision. Endless snacks or reading your favorite story for the entire day? Book lovers may believe this decision is obvious. But I bet the foodies believe that snacks are the only option. By asking questions like these, you'll figure out who's who.

When to Ask It: "This or that" questions are always good for starting or continuing conversations. If there's a lull in talking, break this out to bring back the fun.

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

Why It's Great: It's one of those trick questions! Plenty of introverted people have a great sense of humor. This one can help you find out which is their preference. Even if introverted people can still tell jokes, some people might favor those who are more comfortable in large crowds.

When to Ask It: Dating talk is always juicy! Finding out what someone's dating preference is is always an eye-opening topic.

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

Why It's Great: These are excellent for delving deep into a hypothetical situation. How many random scenarios can you come up with?

When to Ask It: Almost all your pals will enjoy a nice, feel-good "what if" debate about possessing a lot of money! Or, in this case, taking advantage of a private jet.

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

Why It's Great: Forming close bonds with your friends is vital. Knowing what your friends value the most can help you figure out ways you can be better buddies in the future. It's also time for you to assess how you treat your friends! This is my favorite way to see if my pals and I share and have more things in common. After all, we appreciate people who have qualities we like.

When to Ask It: There's no better place to ask this than when you're with a group of friends. That way, you can get as many answers as possible.

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

Why It's Great: Everyone has a part of their history that they don't feel particularly good about. To find out more about someone, it's a good idea to ask them what they would change about their past. Anything about life is always a good, usually deep, topic.

When to Ask It: When discussing someone's childhood, it's an excellent time to use this. Life has many ups and downs, so sharing past experiences is a good way to deepen a bond. If you're with someone you want to get to know better, this would be another perfect time to ask it.

26. Do you recycle?

Why It's Great: It's always intriguing to discover how far your friends will go to recycle. Some may do the bare minimum, while others have become stewards of the planet. Being conscious about what we can do for the environment is a great topic.

When to Ask It: The ideal time to bring up this issue is when discussing greenery or the environment in general. You never know; you might learn a new trick or two about recycling.

27. What makes someone a hero?

Why It's Great: Everyone's definition of a hero is different. Some might imagine a super-powered being with feats of strength, while others think it's only if they help their community. Learning what makes a hero in their eyes might influence your own thoughts.

When to Ask It: Casual but essential questions like this are good to ask when discussing possible role models or people you admire. Whether you talk about heroes from your favorite films or real life, these topics are interesting.

28. Have you ever cried at a movie?

Why It's Great: Everyone has a favorite movie they can't help but cry to. It doesn't matter how tough that person thinks they are; there'll always be a movie that makes them tear up. Questions that expose someone's sensitive side are good for getting to know each other deeper.

When to Ask It: If you want to grow closer with a group of friends, then random questions like this will do the trick.

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

Why It's Great: Questions like this might bring up regrets but can also be comforting as you dive into and share your memories. Prepare for some bittersweet stories, though! 

When to Ask It: Save this discussion for closer friends and family because there's always a chance that it will turn quite serious. 

30. What's your opinion on fate?

Why It's Great: If deep questions 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.

When to Ask It: Keep this one handy and use it when you want deep and personal conversations with your friends or family.

31. Do you have tattoos?

Why It's Great: Tattoos always bring up strong opinions one way or the other. Whether you have tattoos or not, discussing them is always fascinating. Each tattoo has a story; asking about it will bring it to light.

When to Ask It: If you think someone has some hidden tatts, ask away. Most people are proud of their art pieces and will be happy to share their stories.

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

Why It's Great: Money makes the world go around. It's always interesting to see what your pals would buy first if they had unlimited resources. Cars, trips, tickets to their favorite sport, something from their favorite brand?

When to Ask It: Ask questions like these at any point during your conversations. They're also simple enough to ask anyone. Even a child will have a list of things they'd want to buy if they had access to endless cash.

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

Why It's Great: You can unlock great conversations with this. A ten-year plan exposes what your friends and family want most in life. You might learn a thing or two about them by asking. This may seem simple, but the answers might be deeper than ever imagined. 

When to Ask It: Use this when discussing the future. Be sure to give each other time to think; even the most superficial answers may have more to them.

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

Why It's Great: We've all had moments where we go out of our comfort zone to do something we'd never thought we would try. Hearing everyone's stories is always refreshing! And you learn a little something new about them. How wild are your friends, really?

When to Ask It: This is one of those funny random questions you can ask when you've gotten closer but want to know more.

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

Why It's Great: What someone frequently runs out of might reveal something about them. It could be a favorite food item or brand of shampoo. It may seem lame to talk about, but let's be honest; we all want to know what strange things end up on our shopping lists. Next time, you can even buy it for them.

When to Ask It: When you're shopping, of course! A group shopping trip is ripe for conversations like these.

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

Why It's Great: Consider this an easy way to start a humble brag contest between friends. Rock star, singer, scientist? You can all enjoy a little friendly boast.

When to Ask It: This can boost your friends' self-esteem if you feel they could use more positivity. Give them the floor; let them brag a bit!

37. What about us makes you smile?

Why It's Great: Talking about what makes us smile sparks lighthearted conversations. Shared laughter, support, or the little moments that create unforgettable memories. Take time to appreciate each favorite thing that improves your relationship dynamic.

When to Ask It: If you want sweet and loving conversations with your partner, ask this. Whether alone in bed, cooking a meal together, or out for a jog, this is a nice one to ask.

38. What chore do you absolutely hate doing?

Why It's Great: What's the worst thing on your chore list? Everyone has something they avoid doing. You might bond with someone over disliking doing the same thing. A friendship born over complaining about something can be just as good as any other!

When to Ask It: It's fun to ask random questions like these to continue getting-to-know-you conversations. Bring this out, and expect a few playful groans from you both.

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

Why It's Great: This is a good question to find out the most beautiful place they've been to. Your friends will transport you to a location with their vivid descriptions.

When to Ask It: Bring this up during conversations about new places, be it for vacation or work. It's a wonderful way to learn more about their favorite destinations and immerse yourself in the details of those special places.

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

Why It's Great: You get to learn who those role models are. You also get to know what qualities they admire in people they look up to. It can be surprising to understand their answers to this. But it's also refreshing because you get to know your friends on a deeper level.

When to Ask It: When nothing's going on, this is a great way to start an interesting conversation. Whether you're out and about or relaxing together at your favorite place, this is a good one.

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

Why It's Great: This question prompts a discussion about one's fondness for a specific country. And because language is closely linked to culture, there are a lot of ways these conversations can go.

When to Ask It: This works best when discussing travel plans or places you want to visit. Often, these topics involve encountering different languages in various countries.

42. Do you get along with your parents?

Why It's Great: Not everyone is close to their parents, while others keep their parents up to date on their daily activities. It's interesting to see how different people bond with the people who raised them.

When to Ask It: When discussing a topic involving family, particularly one's childhood or upbringing, ask this. It's ideal for a meaningful conversation.

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

Why It's Great: This sparks discussions about a life free from financial worries. It can ignite some wild imaginations and creative ideas, too. It's an opportunity to explore what matters to each person.

When to Ask It: This is perfect for lighthearted and positive conversations with friends. It allows everyone to share their dreams and aspirations in a world without limitations.

44. What habits are holding you back from success?

Why It's Great: This is a good opportunity for everyone to admit their weaknesses. You can suggest changes to break through those problems.
When to Ask It: This is great when you're having a heart-to-heart. A rousing discussion of self-improvement can lift your spirits.

45. What's your personal image of God?

Why It's Great: Talking about God can bring you closer to others who share your beliefs. The concept of God is a sensitive subject, and everyone has their own interpretations of how it connects to their life. Just make sure to be respectful of everyone's opinion when talking about this subject.

When to Ask It: Only ask this when everyone in the group feels safe enough to say what they think. Keep this one for people you feel close to.

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

Why It's Great: Age can shape our priorities, and this one prompts contemplation about long-term aspirations and desires. This will make everyone think about what they want out of life.

When to Ask It: This is best suited for when you're discussing life goals and plans with your friends or family. It encourages everyone to reflect on what truly matters in the grand scheme of things.

47. What do people do too much of today?

Why It's Great: It fosters camaraderie as we find common ground discussing behaviors we dislike in others. Sharing these thoughts among like-minded individuals can deepen bonds.

When to Ask It: Bring it up when your conversation naturally drifts towards discussing other people's actions or habits. It can lead to interesting and relatable discussions.

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

Why It's Great: This sparks intriguing discussions about different perspectives on friendships between genders. It's interesting to hear why some think it's possible while others don't. I once asked a family member this question. They said they believe platonic friendships with the opposite sex are viable and maintainable as long as both of you are mature. I thought they had a valid point!

When to Ask It: Save this interesting question for a time when your group includes a diverse group of people. That way, you can get various responses and insights.

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

Why It's Great: This is one of the questions that foster deep and honest conversations. It allows people to share seldom-discussed aspects of themselves while learning more about each other.

When to Ask It: Choose a private and trustful moment, like with a family member, to ask this question and learn more about each other on a deeper level.

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

Why It's Great: This funny random question will get everyone to think about what word they'll pick. There are so many options, so they'll spend time thinking it over. Then, you can turn it into a game where they can only use their word and some non-verbal cues to answer questions. It's bound to get hilarious!

When to Ask It: You can ask this at any time. You can slip it between small talk or when you're spending some intimate time together.

51. With who did you make your last phone call to?

Why It's Great: Although many of us now prefer texting over talking to someone on the phone, we still make calls now and then. Whoever you ask this to is bound to have an answer. 

When to Ask It: Try this one when you're talking about connecting with people in this digital age. Especially if you notice them scrolling on social media with their phone, use it during a small talk to avoid a boring conversation.

52. What is your all-time favorite song?

Why It's Great: With millions of songs out there, it's impossible to find someone who doesn't have a favorite. You might also discover a new singer or band that you'll love too!

When to Ask It: When you're asking someone about their interests and hobbies, throw this one into the mix. Another time to ask is when you're both listening to music.

53. Would you be a hero or villain for a day?

Why It's Great: There are many reasons to be a hero or a villain. A great way to learn more about someone is to find out whether they want to be good or bad in a hypothetical setting. This could lead to questions about their favorite hero franchises and discussing superpowers!

When to Ask It: This is another great conversation starter that can lead to more extended topics later, so keep it handy. It's great for lighthearted or comic exchanges. 

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

Why It's Great: This is an ongoing debate! Start asking, and people will wonder more about things they typically don't think about.

When to Ask It: This funny question is excellent because it can bring out how passionate some people are about their TP. Start the small talk with this and watch how you become strangers to close friends.

55. Pineapple or Anchovies on pizza?

Why It's Great: These two toppings are the most controversial options a person has to choose from when it comes to pizza. Watch how it becomes the funniest thing to discuss as some of your friends struggle to defend their answers.

When to Ask It: These good random questions are hilarious yet informative at the same time. Next time you order pizza with your friend, be armed with the knowledge of whether to get extra pineapples or anchovies.

56. Green or red grapes?

Why It's Great: It may seem unimportant, like your favorite color, but it's good for random convos. Be surprised how many people will realize that they don't know if there are any differences between them, apart from their color that is. 

When to Ask It: If you want to learn more about your friend's preference, this is another topic you can keep with you!

57. Bathroom singer or dancer in the shower?

Why It's Great: This is extremely relatable and funny. While dancing in the shower might be a little dangerous if you're breaking out big moves, the sprinkler might work. Singing is usually the favorite thing, though. 

When to Ask It: Make sure only to ask this funny random question to friends. Plenty would rather not talk about their shower time with strangers.

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

Why It's Great: With all the zombie apocalypse movies out there, everyone will surely have their own action plan. Just think of your favorite season of a zombie series and consider what you'd do if you were one of the characters stuck in that situation. It's interesting to hear what people would do to stay alive! 

When to Ask It: Ask this one during or after watching a zombie movie or show. You can start a creative discussion with this topic as everyone shares their brilliant ideas.

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

Why It's Great: Hearing some big, controversial reasons for why it happened sets the mood for good old storytelling. And who knows, they might just surprise you!

When to Ask It: Ask away over a few drinks, but it's best to keep this funny question for people you know well. Some people might not feel safe telling their embarrassing secrets to strangers.

60. What was the best thing since sliced bread?

Why It's Great: We've all heard the saying, "The best thing since sliced bread." Now, you get to answer what you think it is. Go wild!

When to Ask It: There's no wrong time to ask this—only incredibly right times. Random questions to ask like these will become your favorite type of questions because you can't go wrong with them.

61. Never have I ever chosen someone over my best friend.

Why It's Great: You'll get some surprising answers. It also reveals fascinating insights into a person's loyalty, priorities, and decision-making process.

When to Ask It: Ensure that their best friend or significant other is in a separate room to avoid any potential issues. Otherwise, feel free to ask away!

62. Never have I ever faced my biggest fear.

Why It's Great: Your friends might have fears you're unaware of. Conversation starters like this get them to open up and help you build trust with them.

When to Ask It: Ask this if you want to learn more about your friends and not just about surface-level things. You can end up having a deep conversation because of this one.

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

Why It's Great: Who doesn't love pancakes? This will show how much of a pancake lover your friends are. The answer to this one can be both hilarious and genuinely impressive.

When to Ask It: Anytime! Random questions to ask about a favorite food memory and the crazy things we're ready to do to get those wonderful meals make for fun conversations.

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

Why It's Great: Kids are ultra-hyper, creative, and always do the weirdest thing. Oh, the days when we could be young and naive! You might find out some absurdly odd stories about your friends. We sure were little rascals as kids, weren't we?

When to Ask It: When everyone's talking about their childhood and reminiscing, add to the nostalgia by asking funny questions like this.

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

Why It's Great: Some people would say famous TV characters. But you'd want them to be resourceful and capable. This will create some fun discussions. Just make sure that they explain why they chose that person.

When to Ask It: This is a tremendous hypothetical question to pop anytime. Maybe even over margaritas. 

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

Why It's Great: Everyone should reveal an embarrassing thing they did to the group for this challenge. Who knows, it might recall a favorite memory. Or one you've been wishing to keep hidden.

When to Ask It: When you ask the right question at the right time, it can create the best atmosphere when hanging out with friends. This one is good when you're all having a good time, maybe even over a game of truth or dare.

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

Why It's Great: It's always interesting to hear what your friends' preferred superpower is and what they plan to do with it. Whether they want to fly, be invisible, or protect others from harm with a super shield, the options are endless. I would choose teleportation. There's no traffic that way.

When to Ask It: This question is a great icebreaker for starting a meaningful conversation with your friends. Be prepared for the exchange to get animated, as discussing what powers and drawbacks you'd have can get lively.

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

Why It's Great: Finding out where your friends like to go to relax is a great way to learn what makes them happy. Ask them what they like about the place.

When to Ask It: When people start talking about what they like, this is a good time to ask to have a meaningful conversation.

69. What are you most grateful for in life?

Why It's Great: Taking the time to be thankful for the things you have in life is essential. Sharing the things we're grateful for makes us, in turn, appreciate them more. See if your friends and loved ones practice daily gratitude. 

When to Ask It: If your friends need positivity or cheering up, you can use random questions like this to help make them feel better. It highlights everything they have and what they might be taking for granted.

70. What's the strangest thing in your refrigerator?

Why It's Great: I'm sure we all have something weird in our fridge. But ask your friends what's the strangest item they have in their fridge, and you might have some unexpected answers.

When to Ask It: A perfect, funny random question when discussing food with friends. Segue nicely, and you'll have a funny moment where you all top each others' weird fridge contents.

Ultimate List of Random Questions To Ask

Question Categories

Random Questions To Ask A Girl

Having random questions to ask a girl is a great way to get her attention and keep it, because with these questions to ask a girl, she'll never know what's coming next. Use these to have the best possible conversations!

  • Whose advice do you always listen to?
  • What about yourself, do you find the most pride in?
  • What’s your favorite place in the world?
  • Would you enjoy a vacation away from all of your technology?
  • What is your version of “There’s two types of people in this world…”?What’s the weirdest thing you’ve ever bought?
  • If you could only eat one food for the rest of your life, what would it be?
  • If you could only own a few things, what would they be?
  • What product would you seriously stockpile if you found out they weren’t going to sell it anymore?What’s your biggest fear?
  • What’s your biggest regret
  • What’s your favorite memory?

Funny Random Questions to Ask a Guy

One excellent thing about random funny questions is that, because they're so unexpected, they make people 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 surprising chuckles, as well as some outright guffaws!

  • If the roses are red, why are violets blue?
  • Can you share your biggest DIY fail story?
  • How do you hang toilet paper: over or under?
  • Have you ever gone to a corner store and stolen a candy bar?
  • What was the most embarrassing thing you did on public transport?
  • How many beers do you think I'd be able to consume?
  • Describe the funniest thing you’ve seen someone doing in Walmart.
  • Do you still sleep with a stuffed toy?
  •  What’s the craziest thing you’ve ever done after getting really drunk?
  • What would you do if you got invisible for a day?
  • What’s your preference: to be buried or be cremated?
  • Describe the funniest smell you have ever smelled.
  • Do mermaids have live babies or lay eggs?

Random Questions That Are Great Conversation Starters For Couples

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. There's no need for a random question generator; just try a few of these!

  • Who is your favorite musician or band?
  • Where did you last travel to?
  • What's your favorite song?
  • When did you last take a flight?
  • What's your favorite type of food?
  • Where is your favorite place to get a drink?
  • What's the best book you've ever read?
  • What is your favorite place to vacation?
  • Who is your favorite author?
  • What is your favorite place to vacation?
  • What book are you reading now?
  • What is your favorite place to vacation?

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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

Move beyond the mundane and aim to have great conversations with everyone. Let me help you unlock a world of meaningful connections!

How do you 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 0ne-two. That's it: two steps.

  1.  Choose your questions. Pick one that fits the audience you're talking to. If it's your boss, don't talk about absurd or scandalous things. If it's your friend, pick questions 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 your great questions, ones that 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!

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 conversations interesting?

Any conversation can be made more interesting by asking the right interesting questions. Ensure you use the ones on our list or any of the many other articles on Mantelligence?

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

It's the same way that you ask follow-up questions. Ask open-ended ones, and just go from there! Avoid questions that can be answered with a yes or no.

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 about them. The timing may be random, but the topic should suit her.

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 talking about an insightful topic. You can also ask about her biggest pet peeve to get her riled up. If you ask these with the right body language, it becomes more compelling than the topic itself.

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. We bet they can't answer them!