115 Interesting Questions To Ask – Spark Fun and Unexpected Conversations

Entertainment By James 

115 Interesting Questions To Ask – Spark Fun and Unexpected Conversations

Entertainment By James 
Show Contents Hide Contents
Contents

When was the last time you had a truly interesting conversation? Think about it for a minute because they tend to be few and far between, right? Well, perhaps the problem is that you’re not asking the right questions. If you ask the same old boring questions all the time like “how was your day” and “how are you doing,” you’ll end up having the same old boring conversations. On the other hand, if you ask unexpected and different questions, you’ll end up having fun and unique conversations. Admittedly, some of these will be a little weird and unusual to ask, but here are 115 interesting questions to ask to spark an unexpected and memorable conversation.

 

Out of This World (14)

 

1. How long do you think you would survive in a zombie apocalypse?

Like it or not, this is something you’ll have to think about sooner or later. You might as well start the conversation now.

 

2. If you knew it could support human life, would you accept a one-way ticket to Mars?

This isn’t as farfetched as it sounds, and if there’s ever a time when living on Mars becomes possible, there probably won’t be any coming back.

 

3. What’s your opinion on self-driving cars becoming a thing during your lifetime?

How could this question not prompt an interesting discussion? Plus, if you’re aware of the latest developments in self-driving cars, you’ll know that they could be here sooner than you think.

 

4. Name three famous people, living or dead, you would invite to a dinner party.

Sure, this would be a small dinner party, but that would just make it easier to talk to all three. Just make sure your three guests are people who will get along with one another; otherwise, your dinner party could soon turn into a disaster.

 

5. If there was a day in your honor, what would people do to celebrate?

This definitely isn’t a question you hear every day. Just think about it as if the rest of the world is a puppet that you’re controlling.

 

6. What’s your plan to take over the world?

Come on, everyone has secretly thought about what it would be like to take over the world and how you would do it. Now’s the time to share your plan.

 

7. What fictional planet do you most want to live on?

Let’s see, you could choose Tatooine or the Planet of the Apes or just about any other world that’s ever been envisioned.

 

8. What would you choose as the 8th wonder of the world?

Quick, do a Google search so you can confirm what the other seven wonders of the world are; that’ll make it easier to come up with something that’s not already on the list.

 

9. What dead historical figure would you like to bring back as your invisible friend?

The key part here is that your new friend will be invisible, which could actually work to your advantage because you wouldn’t have to explain his or her presence to everyone.

 

10. What’s one fact about the universe that blows your mind?

There’s gotta be one thing about the universe that’s always left you puzzled. This is your chance to explain why it blows your mind.

 

11. What’s one question you would like to ask any religious deity?

We’ll be all inclusive with this one, so you can ask God, Allah, Buddha, or any of the hundreds of Hindu deities. Just keep in mind that you only get one question.

 

12. Should Pluto be considered a planet?

For the record, I’m not sure whether or not Pluto is currently considered a planet or not. But now is your chance to weigh in with your opinion on the matter.

 

13. What’s one safe assumption you can make about the world in 25 years?

This is actually a tough question but it should prompt an interesting conversation. Of course, we’re making the assumption that the world will in fact still be around in 25 years.

 

14. What Sci-Fi book or movie created a world you wish you could live in for real?

There’s plenty of flexibility with this one, so the possibilities are endless. Just know that Animal Farm doesn’t technically count as sci-fi, so don’t think you’re going to suddenly turn into a farm animal and become a George Orwell character. On the other hand, 1984 is on the table.

 

 

Your Personal Taste (17)

 

1. If you got in a bar fight, what song would you want playing on the jukebox?

If you’re accustomed to getting into bar fights, this question should be easy to answer. If not, just think about a song that either gets you really pumped up or makes you want to punch something.

 

2. How important is your family?

Do you and your family a favor and answer this question with more than one or two words.

 

3. Name one pet peeve you have that you wish didn’t bother you so much?

It’s not easy keeping your home spotless or correcting everybody’s grammar, is it? Imagine being able to let those things not bother you.

 

4. If you have 30 minutes to kill before you have to go somewhere, what do you do?

In other words, what’s your favorite thing to do that takes 30 minutes but only 30 minutes. Just try to keep it PG-13, okay?

 

5. What’s one thing that gets far too much coverage on the news?

You watch the news, right? Checking to see what’s trending on Twitter doesn’t count. Anyway, there’s probably something that you’re sick of hearing about.

 

6. What’s the most spontaneous thing you’ve ever done?

That has to be a good story behind this, right? If not, you’re probably doing something wrong with your life.

 

7. Describe your family in one word.

Okay, now is the time that you can spend just one word on your family. Just make sure it’s a nice word, huh?

 

8. What makes a person beautiful in your eyes?

Everyone is entitled to their own personal definition of beauty, now’s the time to explain yours.

 

9. When was the last time you truly felt alive?

This isn’t a particularly weird question but it’s one that is so rarely asked. It’s also a great question to get to know someone a little better.

 

10. Do you believe things happen for a reason?

Do you ever roll your eyes when people say that they believe “everything happens for a reason?” Somehow, if you ask someone that instead of letting them volunteer that information, it’s less annoying.

 

11. What’s one restaurant you’re ashamed to admit you like?

Hey, Applebee’s has some tasty items on the menu and you don’t have to be ashamed to admit it anymore?

 

12. Describe yourself using only three words?

“Hard-working, alpha-male, jackhammer,” – Dwight Schrute. You’re probably not going to top that, but you should give it a try anyway.

 

13. What’s something you do differently than other people?

This doesn’t have to be a weird thing like eating cereal with water instead of milk, but there has to be something that separates you from the crowd, and surely it’s worth talking about.

 

14. How willing are you to talk to strangers?

This would actually be a great ice-breaker at networking events when you’re in a room full of strangers. At the same time, it’s also a way of asking someone how trusting they are of people they don’t know.

 

15. What do you want your legacy to be after you’re dead?

This is definitely a loaded question but one that everyone should consider at some point in their lives. Sometimes it requires being asked about it to make it happen.

 

16. What’s one thing that you’re irrationally afraid of?

Okay, you can’t say heights or clowns in response to this question because those things are legitimately scary. However, admitting a weird fear to someone is an interesting conversation waiting to happen.

 

17. What’s one piece of advice you would give to someone half your age?

Feel free to take a minute to think about this question because it’ll require taking a long, hard look at your own life and what mistakes you might have been able to avoid with some better guidance.

 

 

Digging Into Your Past (16)

 

1. What’s the weirdest thing you did as a child?

Don’t be afraid to be honest here; no one’s going to judge you for being weird as a kid. Plus, it should be entertaining to talk about it.

 

2. Name one thing that was cool when you were young but isn’t cool anymore.

This is another question that will require a little bit of thinking. Hopefully, that leads to an interesting conversation that you’ve never had before.

 

3. What do you miss most about being a kid?

Everything has that one thing they wish they could still do, even if it’s just going days without bathing. Of course, that won’t be everybody’s answer, so it should be fun to compare.

 

4. What’s your funniest childhood memory?

Just so you know, funny can be a synonym for embarrassing. That doesn’t mean your funny childhood memory has to be embarrassing, but it’ll probably help.

 

5. What’s the biggest favor another person has ever done for you?

This is not a question anyone will be expecting. It will also force you to think about how other people have helped you, which isn’t a bad thing to think about every now and then.

 

6. What was your first job? Also, what was the first job you actually liked?

It’s time to re-live that summer job at the ice cream stand or working as the nighttime janitor at some department store. It’ll also be telling to think about what job you actually liked.

 

7. What was your favorite meal growing up?

If you had a nice, normal childhood, the answer to this will obviously be dinosaur chicken nuggets with macaroni and cheese. If it’s not, something may have gone horribly wrong.

 

8. Where did you go on your most memorable road trip?

Just so you know, the most memorable road trip isn’t necessarily about the destination. Remember, the journey is what should be memorable, especially if you never actually made it to the destination.

 

9. What’s the nicest compliment you’ve ever received?

We don’t spend enough time talking about all of the good things, so it’s worth it to ask this question and create a little positivity.

 

10. What’s the best city you’ve ever visited?

Now is the time to talk about your favorite vacation destination. If you truly enjoyed your visit to a city, you can probably talk about it for hours on end, huh?

 

11. What job did you want to have when you were growing up?

It probably isn’t the job you have now, but everyone loves reminiscing about the dreams and career goals they had when they were young.

 

12. Name a time when you feared for your life the most?

Admittedly, this is a weird question to ask someone out of the blue, especially if you don’t know them well. But on the chance that someone has a fascinating story to tell, it’s worth asking.

 

13. What’s something you got away with as a child that nobody in your family knows about?

This sounds like a great way to brag about something you did as a kid. Plus, the world needs to know exactly what you buried in your yard that your parents still haven’t found out about.

 

14. How did you meet most of your current friends?

At a certain point, most of us forget how we met our friends, so this can be a topic worth exploring. Also, if there’s a weird story like you met them on MySpace or Friendster year ago, that’s a story worth telling.

 

15. What’s one family tradition that you hated growing up?

This is the perfect time to vent about something you hated as a kid while also saying something bad about your family.

 

16. Who was your biggest arch-nemesis growing up?

Come one, even kids can have enemies. Even if you tried to be nice to everyone, there’s somebody that you never got along with growing up who you consider an enemy. Well, now’s the time to share all of the dirty details.

 

 

Only Hypothetical (21)

 

1. If you could know the truth about one thing, what would it be?

This is a question you have to think about carefully and should lead to an interesting discussion. It could be aliens, the JFK assassination, or the Bermuda Triangle, just don’t forget that you only get to pick one.

 

2. Name one historical figure you would want as your personal mentor?

This question depends on your field. If you’re a writer, you could choose Hemingway or Shakespeare. If you’re a businessman, imagine learning from Henry Ford or Steve Jobs.

 

3. If you were arrested, what crime would your friends and family assume you committed?

This question is all about how your friends and family see you and what kind of person you are. Plus, isn’t it kind of fun to imagine yourself committing a crime without actually committing one?

 

4. If you were a mad scientist and weren’t concerned about money or ethics, what would be your first crazy experiment?

There’s definitely a chance to score points for creativity here. Imagine unleashing a monster on the world or developing a secret potion that turns everyone’s skin green. On the other hand, you could be boring and be a mad scientist who wants to help people.

 

5. What would you do if you were gifted 1,000 acres of land?

To be honest, I don’t know how big an acre is, but 1,000 is definitely a lot of land. Are you building your dream home or maybe building a track for go-kart racing? Either way, that much land should prompt an interesting discussion.

 

6. If you could hack one person’s computer, who would it be?

This is your chance to admit how badly you want to look at your significant other’s computer. But if that’s not your jam, maybe you’d like to break into the computer of a politician or world-renown drug dealer? Just spitballing here.

 

7. If you were forced to flee the country, where would you go?

It’s actually a good idea to have this discussion at some point. After all, you’ll want to be prepared just in case the day comes when you really do have to flee the country for some reason. But don’t worry, there are plenty of great options.

 

8. What do you think you’ll be nostalgic about in 40 years?

It’s not easy looking 40 years into the future. However, if you can do it, you’ll have a window into what really matters to you in the present, which could spark an interesting chat.

 

9. If you could get anything you wanted for free from one store the rest of your life, what would it be?

Obviously, you’re not going to choose the Dollar Store, but there are plenty of high-end stores that would be wonderful to shop at for free. You just have to weigh the pros and cons of each and only pick one.

 

10. If you had to bury a treasure chest, where would you hide it?

Not enough of us ever think about what it would be like to be a real-life pirate. It’s a weird topic, but it definitely warrants a discussion.

 

11. What would you do if someone gave you a one-minute commercial to fill during the Super Bowl?

Think about it, you have one minute to say anything you want in front of everyone watching the Super Bowl. There are so many possibilities to discuss.

 

12. If you could master what sport, what would it be?

To be clear, this doesn’t have to be a sport you’ve actually played. It’s more so what skills you wish you had and what athletes you’d like to emulate the most.

 

13. If tomorrow was your last day on earth, what would you do?

Sure, this may sound a little morbid, but there’s a lot you can do in a day, giving you a lot to talk about.

 

14. If you could snap your fingers and learn a language, what language would you learn?

There’s actually a lot to discuss here. Do you want to learn a language that’s difficult to learn or do you want to learn a language that can be the most useful to you?

 

15. What’s one law you wish you could create?

Okay, you’re not exactly an emperor, but you do get to pick one law to impose on the world, so discuss and choose carefully.

 

16. If you could swim in any liquid, what would it be?

Ever wonder what it’d be like to swim in a pool of coffee or orange soda? Me neither, but let’s talk about it anyway.

 

17. If you could make war illegal, how do you think countries should settle disputes instead?

There’s really no wrong answer to this, which is why it should prompt an interesting debate. Personally, thumb wrestling among world leaders would be fascinating to watch.

 

18. Name one thing you’d like to eliminate from your daily schedule?

This one has so many options that an interesting discussion seems inevitable. Just try not to be gross and choose going to the bathroom, not that one could argue against it.

 

19. What’s the first thing you would buy if you won the lottery?

There’s no wrong answer to this, but there can definitely be a difference of opinion that will lead to a good discussion.

 

20. If you had to share your name with a city, state, or country, what would it be?

Surely you’ve met people with names like Montana and Georgia before, but now is the time to flex your creativity muscles and come up with a name like Armenia or Tuvalu.

 

21. If you had to subsist off of one candy bar the rest of your life, what would it be?

Snickers and PayDay may be your best options, as the peanuts will be a good source of protein. But isn’t there a better option you’d like to eat non-stop the rest of your life?

 

 

Cause I Want to Know (16)

 

1. What “old person thing” do you like to do?

Don’t act like you don’t know what “old person thing” means. Maybe you like eating dinner at 4:30 or secretly enjoy a glass of prune juice every now and then. Perhaps you’re secretly good at Mahjong. Whatever it is, it’s time to share it with the world.

 

2. What’s the most unprofessional thing you’ve ever done?

Unless you’re having a conversation with your boss, this should be a safe space, so it shouldn’t matter how you answer this.

 

3. What’s one thing you learned but only after it was too late?

The answer to this is probably going to be embarrassing. But everyone has something, so this question should lead to a good talk.

 

4. If you were in a cult, would you want to be a follower or a leader?

“You have more fun as a follower but you make more money as a leader” – Creed Bratton. Keep this in mind when you answer. Also, don’t lose sight of the fact that we’re talking about a cult that will probably end with a mass suicide.

 

5. What was the last thing you re-gifted to someone?

Don’t pretend like you’ve never re-gifted something, so just come clean about it and we’ll have a good laugh.

 

6. Name one thing that puzzles you every time you think about it.

The world is a confusing place, so there has to be something that you just don’t get. Well, now’s your time to talk/complain about it.

 

7. What’s your most ridiculous life goal?

Look, bucket lists aren’t meant to be completed. What’s the fun if everything on there is so easy to accomplish? There has to be something that’s too crazy to be accomplished.

 

8. What’s the meanest thing you’ve ever done to someone?

Sometimes it’s good to talk about a moment that wasn’t your proudest. This could be a difficult thing to talk about, but it should be a conversation worth having.

 

9. Would you break the law in order to help a loved one?

To be fair, there are a lot of variables with this question. Technically, jay-walking is breaking the law. But wouldn’t it be fun to talk about just how much you’re willing to skirt the law to help your friends and family.

 

10. What’s the craziest thing a boss has ever asked you to do?

Okay, so this question feels like it could lead to talking about a lawsuit or a criminal complaint. But maybe you can think of something that was fun-crazy that your boss asked you to do.

 

11. What’s the weirdest dream you ever remember having?

There’s nothing to be embarrassed about here because dreams are out of your control. They also tend to lead to fascinating conversations.

 

12. What’s the weirdest conversation you’ve ever overheard?

Don’t pretend like you’ve never eavesdropped before. There has to be something you overheard once that completely blew your mind in either a shocking or hilarious way.

 

13. What was the most awkward moment of your life?

Look, we’ve all been to middle school before so no one’s going to judge because we’ve all been there before.

 

14. What social or political issue do you feel strongest about?

This one may not lead to a funny conversation but there’s nothing wrong with expressing your opinion on something.

 

15. What is the biggest regret of your life?

We’re not trying to lead you down a dark road with this question. However, it sometimes helps to share these things with someone else.

 

16. What’s one secret you’ve kept without telling anybody?

Ironically, this won’t be a secret much longer. Even if you’ve kept a secret for a long time, sometimes it’s good to get these things off your chest.

 

 

Pop Culture Stuff (18)

 

1. What movie can you quote from start to finish?

Time to prove it. Roll opening credits and take it away…

 

2. What cartoon did you watch as a kid that you still watch?

Either you were watching inappropriate cartoons as a kid or you never grew up and still childish cartoons. Either way, you have some explaining to do.

 

3. What’s your favorite fairy tale?

It doesn’t matter how old you are, there’s always a fairy tale that’s stuck with you.

 

4. What Simpsons character do you most closely resemble?

There are plenty of options here, which should lead to a good discussion. However, there are few characters on The Simpsons that are actually worth emulating.

 

5. Name one movie you could watch on a loop for 24 hours straight.

No matter how much you love a movie, watching it for 24 hours straight could make you sick of it. Your best bet could be a long movie because you’ll have to watch it a few less times.

 

6. What life event have you lived through that would make a great movie?

No one’s saying you have to write the screenplay yourself but make your pitch.

 

7. Who would you want to play you in a movie about your life?

Look, we’d all like the best-looking actors to play us in a movie, but you also have to explain why that person would be the right choice to play you.

 

8. What was the weirdest book you’ve ever read?

This kind of questions always requires an explanation, which is why it should lead to a good conversation.

 

9. What classic book do you absolutely hate?

If you’ve ever actually read all 500-plus pages of Moby Dick, that’ll probably be your answer. Otherwise, there’s probably some other classic that you just hated.

 

10. What’s one podcast you couldn’t live without?

In today’s world, it’s only pertinent that we take some time to discuss podcasts. Hope you have some good recommendations.

 

11. What was the last movie that made you cry?

There’s nothing wrong with crying at a good movie. However, unless the movie is a bonafide tearjerker or chick flick, you may have some explaining to do.

 

12. Who are you most ashamed to follow on Twitter or Instagram?

If you follow any of the Kardashians online, now is the time to come clean.

 

13. What celebrity do you inexplicably have a crush on?

We all have our own unique tastes, so just try to put yours into words.

 

14. What song do you make sure you listen to at least once a day?

There’s probably a few wrong answers to this question, but more than anything it’s just something that’ll be interesting to learn about someone.

 

15. What’s your favorite all-time painting?

Come on, think, you know the name of at least one painting, right? Your fall back can be the Mona Lisa, but is that really your all-time favorite?

 

16. What’s your least-unfavorite Shakespeare play?

Okay, nobody is going to force you to like Shakespeare, but there has to be at least one play that you dislike a little less than the others. Not to influence you or anything, but Hamlet has a skull in it.

 

17. What’s your favorite Taylor Swift song?

Don’t pretend like there’s not at least one Taylor Swift song that gets your juices flowing. In fact, the correct answer to this question is, “Don’t make me choose just one.”

 

18. What terrible movie do you think they should remake so they can get it right?

We’ve all seen bad movies that had potential. Now is the chance to share your pick.

 

 

Would You Rather (18)

 

1. Would you rather be in a real-life version of The Walking Dead or Game of Thrones?

Surviving in either of these worlds isn’t going to be easy, so good luck with this choice.

 

2. What you rather spend a night in a crowded dance club or have a small get together with a few close friends?

Oddly enough, this question can tell you just about everything you need to know about a person.

 

3. Would you rather be the worst player in the NBA or the world’s greatest cricket player?

It should be interesting to talk through whether you want to be the best at a sport so few places in the world care about or sit at the end of the bench in front of thousands every night.

 

4. Would you rather be Yoda or Darth Vader?

Yoda seems like the obvious choice because he’s the good guy. But it’s worth discussing because of the fear that Darth Vader commands. That’s gotta be worth something, right?

 

5. Would you rather work seven days a week and retire at 40 or work five days a week and retire at 60?

If you’re going to be a workaholic, it’s at least nice to know there’s a reward waiting for you at the end. Still, there’s nothing wrong with doing things the old-fashioned way.

 

6. Would you rather visit an amazing city but stay in a 2-star hotel or visit a boring city but stay in a 5-star hotel?

If you visit a truly terrible city, you could probably spend the entire time inside the 5-star hotel, but is that really the point of traveling?

 

7. Would you rather have a surprise birthday party or plan out every single detail of your birthday party?

This is a good chance to explain why you’re either a control freak or why you prefer to just go with the flow. Of course, the other option is that you’re just too lazy to plan things.

 

8. Would you rather spend a week traveling back in time or traveling forward in time?

There’s no wrong answer here, which is why it’ll be a good topic of conversation.

 

9. Would you rather exercise constantly but eat whatever you want or watch your diet carefully but never have to exercise?

Again, there’s no right or wrong choice, but you should be able to back up your answer and convince your conversation partner why you’re right.

 

10. Would you rather be rich and lonely or poor and happily married?

This is a classic “would you rather” question that almost always prompts an interesting conversation.

 

11. Would you rather be blind or unable to speak?

We’ve added a little twist to the blind vs deaf debate. You’ll still be able to hear, which is fun, but keep in mind how frustrating it can be to not be able to communicate with people via speaking.

 

12. Would you rather be the first or the last to die among your group of friends?

Sure, this is a little morbid. But it’s at least worth the discussion whether or not you want to watch all of your friends pass away one by one just so you can live a little longer.

 

13. Would you rather have three wishes now or 10 wishes 10 years from now?

Ah, the genie paradox. This when you explain to someone why you’re willing to wait 10 years in order to get three times as many wishes.

 

14. Would you rather spend a year in jail or a year being homeless?

it’s easy to say you’d choose anything over jail, but being homeless is actually a lot of work, so this question is more difficult than you think and worth talking about.

 

15. Would you rather take cold showers for a week or not shower at all for a week?

Exactly how long do you think you can get by before people start to notice you haven’t been showering?

 

16. Would you rather have your flight delayed 12 hours or the airline lose your luggage?

Even if you’re good at killing time in an airport (i.e. going to the airport bar), 12 hours is a long time. But how does it compare to the inconvenience of losing your luggage?

 

17. Would you rather play games knowing you’ll never win or never play games again?

Admit it, you don’t really play games just for the fun of it, do you?

 

18. Would you rather be a vegan or only be allowed to eat meat?

This is how nature works. Most animals eat either only plants or only meat. No matter how much you like meat, this is a question you actually have to think about and discuss.