85 Fun Questions To Ask To Spark An Engaging Conversation

Entertainment By James 

85 Fun Questions To Ask To Spark An Engaging Conversation

Entertainment By James 
Show Contents Hide Contents

When you meet someone for the first time or you’re looking to show someone a good time, it’s usually not a good idea to bog them down with heavy and serious questions. Instead, you want to spark a pleasant and engaging conversation by asking fun or somewhat silly questions. Yes, there’ll be time for all of that later, but when you want to spark a fun conversation, here are the questions you should be asking.



All About You (25)


1. What was your favorite toy growing up?

Who doesn’t love taking a stroll down memory lane? This isn’t the most conventional question, but everybody will enjoy remembering their favorite toy.


2. What’s your favorite childhood memory?

While we’re talking about toys, why not ask about a favorite childhood memory. Even if you can’t remember much, something must stand out.


3. What’s the best piece of advice you’ve ever received?

In a way, you’re asking the other person to give you advice. However, it can be interesting to compare the kind of advice both parties have received in life and whether or not it seems to be working.


4. If you could give yourself a nickname, what would it be?

Everyone deserves the chance to give themselves their own nickname, don’t you think? Forget about whatever nicknames other people have bestowed upon you and let’s start brainstorming some new and exciting nicknames.


5. What’s your proudest accomplishment?

What could be more fun than taking a few minutes to brag about yourself? It doesn’t sound like the worst thing in the world, right?


6. How do you cheer yourself up during a bad day?

This could be an interesting topic. Everyone has a bad day every now and then and it never hurts to talk about what you do to turn things around.


7. Are you more likely to survive without coffee or without alcohol?

There’s no easy answer to this, which should spark a great conversation and perhaps even a lively debate about which one would be easier to live without.


8. How many days in a row will you wear a pair of pants before washing them?

Admittedly, this question is a little on the gross side. That being said, everyone is free to their own opinion and their own hygiene choices, which should lead to a good discussion.


9. What’s your favorite snack?

We always seem to talk about favorite meals and restaurants, but why do we always ignore snacks? There’s an infinite number of choices, which should lead to a spirited debate.


10. What’s one food you’ll never eat no matter what?

You don’t want to make a habit of bonding over things you don’t like, but food is always the exception. You can go a long way talking about broccoli, kale, and rabbit stew.


11. What was your favorite book as a child?

Yes, we’re back to talking about your childhood, but there are so many great children’s books out there, and they deserve to be talked about.


12. If you could only shop at one store for the rest of your life, what would it be?

You don’t want to get to know someone based solely on hypothetical questions, but finding just one store to buy your goodies the rest of your life could be an interesting topic.


13. What household chores do you secretly enjoy?

Anytime you can get someone to tell you a secret, you’re on the verge of an interesting conversation, even if it’s about doing chores.


14. What sports would you be more likely to watch if the players were forced to play drunk?

Again, this is a hypothetical question, but one that allows the imagination to run free. It’s not like you’re going to actually be playing the sport drunk, so there’s no harm in discussing it.


15. What conspiracy theory are you certain is true?

Come on, who doesn’t love talking about conspiracy theories. Anyone who doesn’t is probably the most boring person on the planet. Even if two people can’t agree on conspiracy theories being true or not, the debate should be fun.


16. If whipped cream was being renamed, what would be your suggestion?

You don’t have to be a marketing executive to come up with a good suggestion. Also, there’s no rule saying you can stop at just one idea, so this conversation could last a while.


17. What’s your favorite inside joke?

Obviously, telling someone an inside joke is going to take some explaining, but if it’s a good inside joke, it’ll be worth the long story.


18. What’s the strangest dream you ever remember having?

Is it just me or do people not talk about their dreams often enough? Well, at least the kind of dreams you have at night. Sure, it’s a little personal, but it’s bound to lead to an interesting conversation.


19. What’s your most unpopular opinion?

We all have things we believe that nobody seems to understand. This is a good chance to state your case with a fresh set of ears who hasn’t heard your wildly unpopular opinion before.


20. What’s your favorite outfit?

You don’t have to be fashion forward to have a favorite outfit. There’s nothing wrong with telling someone why you like a particular T-shirt or the special meaning behind your favorite pair of jeans.


21. What item on your bucket list will be the most difficult?

Everyone has a bucket list, and let’s be honest, some of the things on there are going to take a lot of work, money, and luck to accomplish. But this is your chance to explain how you’re going to make it happen and why it’s so important.


22. What holiday do you wish the world would stop celebrating altogether?

No matter how much you love holidays, there’s always one that you can’t stand. Are you sick of being lonely on Valentine’s Day? Are you tired of the commercialism of Christmas? Maybe you just hate trees and can’t stand Arbor Day. Whatever it is, let it out.


23. What’s the spiciest thing you’ve ever eaten?

Compared to sweet or salty foods, spicy foods always seem to come with an interesting story. They’re just a little more intense than ordinary foods, so this is a great food question to ask.


24. Have you ever been in a food fight?

If the answer is “no,” you might as well stop talking right here and now. I mean, how boring can you get? Everyone who’s been in a food fight can tell you that they are both fun and messy, and anything that’s fun and messy will make for a great conversation.


25. What’s one secret you’ve never told anyone?

Once again, it’s time to get the other person to share a secret. Let’s be honest, there’s no such thing as a boring secret, so if you can get a confession out of the person, it’ll get the conversation flowing.


People, People, People (20)


1. How would you grade your parents on a scale of 1-10?

It’s not like your parents are going to be sitting there listening to you, so you’re free to be completely honest when talking about this subject. Also, the lower the score, the more interesting the conversation that will follow.


2. Who’s more likely to get arrested, your mom or your dad?

While we’re on the subject of parents, this should be a fun topic to explore. Most of us don’t think of our parents as lawbreakers, and unless one of them has a criminal record, it should be interesting to think about.


3. What school teacher did you dislike the most?

You could ask someone about their favorite teacher, but doesn’t it seem like more fun to trash talk a teacher that you didn’t like?


4. What personality trait of yours annoys other people the most?

It’s not always easy to put yourself in someone’s shoes, but just give it a try. You might find that it’s fun and useful to look at yourself through someone else’s eyes.


5. What are the three questions you’ve always wanted to ask your pet?

If you’ve ever owned a pet, you know there are things you’ve always wanted to ask it, like “Why don’t you just shut up?” and “How come you’re not eating?” Hopefully, you have more creative questions that are specific to your pet.


6. What’s the funniest thing you’ve ever seen a stranger do?

This one might take a little thinking, but surely there’s been a time when you saw a stranger fall into a fountain at a mall or yell and scream like a crazy person in public. Whatever it is, there’s probably an interesting story to tell.


7. Who’s the funniest person you know?

As long as you say the name of a person and not a dog, it’s a good answer. That should also open up a conversation about what makes a person funny.


8. If you could be best friends with a fictional character, who would it be?

So many times, we fantasize about being with a fictional character romantically, but just try to imagine a fictional character you want to hang out with every day like you two are BFFs.


9. If you could be best friends with a historical figure, who would it be?

Similar question, but think about famous historical figures. I mean, would Benjamin Franklin or George Washington be a cool best friend? Just know that if you pick a brutal dictator or war criminal that you’ll have some explaining to do.


10. If you could choose one person whose mind you could read, who would it be?

This could be a fun topic to talk about. If you can read a person’s mind, you can conceivably manipulate them or just stay one step ahead of them. Just keep in mind that you have to be ready to explain why you would do that to them.


11. What social norms confuse you?

To be fair, it’s going to take a little bit of bravery to discuss this topic with someone. But it’s a good way to express a little bit of confusion and frustration. For instance, why do we have to bring something to eat or drink when we’re invited to someone’s house? Why is it “weird” to eat certain things for breakfast but not dinner? Let’s call this an airing of grievances.


12. What’s the strangest piece of furniture you’ve seen in someone else’s home?

Unless that person is sitting within earshot, it’s perfectly fine to trash their taste in furniture. Let’s be honest, it’s fun to criticize sometimes, and this is a safe space, so let it rip.


13. What are the strangest nicknames you have for your friends?

If you have strange nicknames for your friends, there must be a funny story behind them. What could be more fun and entertaining than re-living how those nicknames came to be?


14. What’s the most ridiculous name someone you know gave to a child?

Let’s be honest, people these days are going crazy when it comes to giving their kids unusual names. We can deal with Khaleesi and Katniss being used for real people, but the line has to be drawn at Chairish or Hurricane, right? What weird example have you heard?


15. Name someone you know who you think should be in an insane asylum?

Yes, this is a little insulting, but if that person isn’t around to hear it, there’s no problem. Plus, we should be taking the stigma off mental illness, right?


16. Who in your life would make a great clown?

Again, this could come off as a little mean, but is it really so bad to say that someone you know would be great at acting funny and entertaining kids? Plus, it’ll make for an interesting conversation while you try to explain why someone you know would be the perfect clown.


17. What character from literature would you most like to marry?

Okay, now is the time to start fantasizing about your romantic life. But let’s take celebrities off the table and focus solely on the people from books you’ve fallen in love with.


18. What makes you stand out among your group of friends?

This is a more subtle opportunity to brag about yourself. Of course, most friends have a lot in common, but there’s got to be something that separates you from the pack.


19. What’s the strangest religious belief somebody told you they had?

In other words, do you know any Mormons or Scientologists? If you scratch the surface of either one of those faiths, you’ll find a goldmine or weird religious stuff.


20. If you died and went to hell, who would be the first person you’d see?

Sure, this is a little grim, but this is really just a way of asking someone who the last person, living or dead, they would ever want to see face-to-face.



Oh, the Places You’ll Go (15)


1. If you could time travel, what year would you go back to?

There’s no such thing as a boring conversation about time travel. It’s a little weird to ask out of the blue, but once you get the ball rolling, there will be a lot to talk about.


2. What’s your favorite travel destination?

Even people who have been on a lot of vacations always have their favorite. So go ahead and make the case for why your favorite travel spot is the greatest place in the world.


3. What’s the best concert you’ve ever attended?

Any question that forces the other person to take a stroll down memory lane is a good conversation topic. Plus, everybody has that one concert from their youth that they’ll remember forever.


4. What is your ideal vacation?

Okay, this is a little different from asking about someone’s favorite vacation destination. There are no limits, so just let the imagination run wild with ideas.


5. What do you do when you get home from a vacation?

This feels like a rather odd question, but even vacations can be a little hectic and stressful when you consider the travel involved. Besides, you can’t just go from vacation back to work, so it’s interesting to learn how other people make that transition.


6. If you had to move to a different state, where would you move to?

There are plenty of options for this hypothetical, but almost too many options. Also, don’t just say Hawaii; obviously, we’d all go there if we could, so try to be creative if you want to spark a fun conversation.


7. What was the most disgusting place you’ve ever gone to the bathroom?

This topic is definitely a little out of left field, but sometimes that can be a good thing. The specifics may be a little gross, but if you have the right mindset, it can be a fun conversation, especially since you probably won’t be going back to that place anytime soon.


8. What amusement park would you most like to visit as the only person in the park?

This is another great question that forces the person you’re speaking with to use a little creativity. Disney World would be the obvious choice for most people. However, no one else there, so think long and hard about the answer.


9. What country or city’s accent would you most like to have?

No one’s saying there’s something wrong with your current accent or lack of accent, but there’s go to be some accent out there you’ve always wanted to emulate. You’ve probably never thought about this before, but that’s why it’s a great topic for conversation.


10. Where was the most beautiful sunset you’ve ever seen?

This is a simple enough question, but surely the answer is something that should be shared with someone.


11. What’s your favorite place to take a date?

Just don’t say dinner and a movie. Think about when you really like someone and you want to do something special or take them somewhere unique. What’s that place?


12. What foreign country are you dying to visit?

Traveling abroad isn’t easy or cheap, so most people haven’t visited the one country that’s always fascinated. But here’s your chance to share that dream with someone.


13. What is the most elegant and fancy hotel you’ve ever stayed?

Most of us aren’t staying in five-star hotels every time we leave home, but surely somewhere you’ve stayed once upon a time has had you in awe.


14. What was the longest road trip you’ve ever taken?

Even if most of the trip was spent sitting in the car doing nothing, something eventful had to have happened last some point. Remember, road trips almost always have great stories attached, which is why they’re great topics of conversation.


15. Are you more likely to spend a weekend at a 5-star resort or a cabin in the woods?

Part of the answer to this will be tied to a person’s finances, but you’re also finding out whether the person you’re talking to wants to be pampered or just wants to hang out in a secluded location away from everyone else.


What Are You Watching? (15)


1. What movie do you think should have a sequel but doesn’t?

If pressed, we can all name a movie that we liked so much that we wanted to see a sequel to it more than anything else.


2. Name one song that would be on the soundtrack of your life?

Let’s be clear, this isn’t necessarily your favorite song. Instead, these are the songs that encapsulate your life, for better or worse.


3. What’s one phrase you say a lot that you’ve stolen from movies or TV?

Keep in mind that you will be judged for your answer to this question. It better be from an all-time great movie or TV show, and I don’t mean Clueless.


4. What’s your favorite guilty pleasure movie?

We know going in that this is your guilty pleasure movie, so you won’t be judged too harshly. That means you can just have fun with your answer, even if you have to defend your choice a little.


5. What TV show do you often plan your day around watching?

Unless your answer is re-runs of The Big Bang Theory, there’s no wrong answer to this question.


6. What movie ending would you like to change?

This question should definitely help to spark a lively debate. With so many movies, it’s tough to envision them ending any other way, which is why you have to be ready to defend your choice.


7. What children’s movie would you choose as the only movie you could watch the rest of your life?

This is definitely an odd question that will force you to do some soul searching. Could you be happy if you could only watch Frozen the rest of your life? Maybe you’d have to go with Babe: Pig in the City.


8. What was the last show you binge-watched from the time you woke up to the time you went to sleep?

We’re talking about doing absolutely nothing else that day but eat, sleep, and binge-watch a show, so you need a good answer. However, whether the person you’re talking to loves or hates your choice, there’ll be a lot to talk about.


9. What’s the funniest video you’ve ever watched on YouTube?

Do people still watch YouTube for the funny videos? Admittedly, this question could be a little dated, but there has to be some ridiculous video that you still remember.


10. If you could become a character in any TV show, what would it be?

The correct answer to this is Zack Morris in Saved by the Bell, but if you remain open-minded to other possibilities, it’ll lead to a fun conversation.


11. What canceled TV show would you love to get a reboot?

There are so many deserving shows out there, so whatever your choice, there’s bound to be a heated debate.


12. What game show would you most like to be a contestant on?

This is not only a good conversation topic, but it’s also a great way to get to know the person you’re talking to better. Let’s be honest, there’s a big difference between wanting to be on Jeopardy and wanting to be on Family Feud.


13. What reality TV show would you most like to be on?

Be careful what you pick here; there’s a lot of trashy shows out there that nobody should ever aspire to being on.


14. What movie makes you cry every time you see it?

There are plenty of acceptable movies for this question, just make sure you pick them or else a fun conversation turns into an inquisition.


15. What’s the longest book you’ve ever read?

Okay, this question is designed to let you brag a little bit. You can talk about your favorite books, and that’s fine. But why not complain about how long and boring Moby Dick was while bragging that you actually made it to the good parts at the end.


Would You Rather (10)


1. Would you rather burp every time you try to kiss someone or drool every time you talk?

Either option is going to put a major crimp in your social life, which is why it’ll make for a fascinating conversation, weighing the pros and cons of each option.


2. Would you rather never brush your teeth or never take a shower?

Again, this is going to force an interesting conversation about which option is easier to manage for your social life. Let’s be honest, either one is going to catch up to you sooner or later.


3. Would you rather sleep while handcuffed to your bed or sleep in a bed that’s too small?

How much do you value getting a good night sleep? Either way, your comfort level could be a little limited. Nevertheless, a choice must be made.


4. Would you rather uncontrollably laugh whenever someone talks to you or uncontrollably cry?

This is far from a conventional conversation topic, but you will learn about someone from the answer.


5. Would you rather eat a hot dog with no toppings or a burger with no toppings?

For the record, both of these options are blasphemous and an insult to grill masters everywhere. Alas, it should spark an interesting debate.


6. Would you rather fight one horse or 100 ducks?

There are a lot of variations of this question floating around the Internet, but let’s keep this simple. Going one-on-one with a horse sounds difficult and dangerous, but being surrounded by 100 angry ducks doesn’t sound like a picnic either.


7. Would you rather address everyone you speak to as “dumbass” or “babe?”

You might think taking “babe” is the safer approach, but would you really want to use that to address every relative and every stranger? It’s a tough call, which is why it’ll lead to a fun conversation.


8. Would you rather go to the bathroom outside or use a litter box in the middle of your living room?

Essentially, would you rather be a dog or cat when it comes to relieving yourself?


9. Would you rather give up texting or give up shopping?

Technically, you could still call people on the phone without having to give up shopping, which gives you an out. But we’re going to find out just how much you love texting.


10. Would you rather have a pet chimpanzee or have no pet at all?

Sure, people love pets, but is it really worth it to have a wild, untamed animal as a pet? It’s a tough call and a fun hypothetical.