Having fun questions to ask in your repertoire is a must!

Why do you need them?

First impressions last.

It’s why you you wear your best clothes to an interview and scrub every inch of your body before a first date.

The key to making a great first impression? Knowing fun questions to ask the people that you meet.

When you have a stack of interesting questions to ask, you allow the people you meet to talk about their favorite subject: themselves. That's where my expertise in conversation comes in. My works have been published on Brit+Co and Elite Daily, so you're in good hands.

Asking a person questions about him or herself is a great way to make a positive first impression. Make use of these fun questions to help new people open up. And walk away remembering how good you made them feel.

Let's begin!


Best Fun Questions to Ask

1. What accomplishment are you most proud of?

Why It's Great: This is a fun question since everyone loves a chance to brag a little bit. It's an opportunity to tell others what they're proud of without sounding like a show-off.

When To Ask It: Talking about personal achievements might not always come around. But you can use this as a positive icebreaker for a change to help give people the ego boost they deserve!

Who to Ask It To: The best part about this great question is that everyone will benefit when asked!

2. Can I get you another drink?

Why It's Great: Plenty of fun conversations can be had with a simple question like this. Sometimes, you only need a little 'spirit' to initiate a fun conversation.

When To Ask It:Ask this when you're out with people in a bar. Make sure to use this golden question to keep the conversation going.

Who to Ask It To: You can ask anyone interested in talking to you. Just make sure that you know that this person actually likes having you around!

3. If you had to pick a new name for yourself, what name would you pick?

Why It's Great: Some names seem to fit certain personalities. Names make up our identities. But if you had the chance to choose a name for yourself, would you pick one based on what you like or what sounds cool to you?

When To Ask It: Any topic that involves making a big change will work with this kind of question.

Who to Ask It To: This question is perfect for almost any person that you meet! Almost everyone has an option in their mind if they have no choice but to change their name!

4. Do you feel like a leader or a follower?

Why It's Great: Some people might think that being a leader means you're the greatest person in the group. But some strong followers make a great leader. This question will have you pondering based on the answers you hear when you ask this question.

When To Ask It: Deep questions about society can be beneficial. This question can help determine the value of a responsible leader and a loyal follower.

Who to Ask It To: Ask this question to any team member, such as at work or school to help establish roles early on.

5. What’s the most courageous thing you’ve ever done?

Why It's Great: Breaking through your comfort zone is scary but rewarding in the end. Accomplishment stories can help bolster your self-confidence. It can also give them a nice ego boost.

When To Ask It: If you need to cheer someone up, this question can help make their day. You can also add this question when there's a topic about doing something new for the first time.

Who to Ask It To: Any good friend who is down and needs cheering up is perfect for this question.

6. When you’re having a bad day, what do you do to make yourself feel better?

Why It's Great: Finding out what each person does to cheer themselves up is interesting. And it can also give you an idea to brighten their day in the future as well.

When To Ask It: Sad conversations can bring the entire energy down. Make sure to use this question to help make the mood a little lighter!

Who to Ask It To: Ask this to have an idea of how to cheer someone close to you up. They could be your close family member, friend, or even partner.

7. What are your movie theater popcorn habits?

Why It's Great: Popcorn is what almost everyone eats when watching their favorite movie. However, you might find out that some people have different theater popcorn habits. Aren't you curious to know about them?

When To Ask It: Any conversation that involves going to the cinema is a good time to ask a question like this.

Who to Ask It To: Ask this question to a friend or your partner to know what to expect! That way, you won't be surprised, especially if you're going to share it with them.

8. What is your favorite Wikipedia article?

Why It's Great: Wikipedia is the ultimate mankind's collection of knowledge. I'm sure when you were in high school; you visited Wikipedia at least once or twice to research your homework. At least I did. That's why a lot of folks can relate to this fun question.

When To Ask It: Ask this while doing an assignment or a task together. Having a little break now and then won't hurt.

Who to Ask It To: Perfect question to ask any team member from school or work.

9. What’s your favorite cheesy pick-up line?

Why It's Great: Cheesy lines are often overrated to the point that no one wants to use them anymore. However, they're well-used for a reason, and that's because they can work. Ask around what favorite cheesy pick-up line they like to hear or even use.

When To Ask It: Dating scenes are some of the best examples of when you can throw this question.

Who to Ask It To: Friends and your partner are the ideal people that would respond best when asked this question.

10. Which of your friends are you proudest of? Why?

Why It's Great: A person who can recognize greatness in others is the person you want to keep around. There's nothing wrong with showing appreciation to people that you care for!

When To Ask It: Use this opportunity to help your friends know you are cheering them on!

Who to Ask It To: A close group of friends is ideal when asking this question. It's also great if the person you're complimenting is with you in the conversation!

11. On a scale of 1-10, how strict were your parents?

Why It's Great: Since you give people a choice on a scale, you can usually hear funny examples of how strict their parents are. Parents are a great source of stories on either end of the scale.

When To Ask It: Ask this when you're talking about childhood experiences. It'll be fun to talk about things you could and couldn't do as a little kid.

Who to Ask It To: Ask this when you're out with your buddies near your age, reminiscing about the good old days.

12. Who was your worst teacher? Why?

Why It's Great: Bad teachers are the stuff of nightmares. I still remember that day when my teacher asked me to do the most embarrassing thing I could think of. She made me 'butt-spell' my name in front of the other class. Yes, I was a little bit silly back then.

When To Ask It: Great to ask when you're just hanging out with your friends anywhere! This is one of the good questions to ask to start a fun conversation.

Who to Ask It To: Best to ask this question with your former classmates! You may have the same teacher in mind.

13. Who was your favorite teacher? Why?

Why It's Great: Great teachers can change a student's life forever. This is one of the random questions you can ask that can lead to meaningful conversations. I still connect with some of my teachers through social media. Because without them, I probably won't be here, where I am.

When To Ask It: This is a good follow-up question to the question above. Ask this when you're at a class reunion!

Who to Ask It To: Best to ask this one with your former classmates or workmates.

14. What was your favorite toy growing up?

Why It's Great: Childhood toys keep their sentimental value for life. This reminds me of my favorite childhood movie- Toy Story. This is a good open-ended question to make someone think about their favorite memory.

When To Ask It: Perfect to ask during a family reunion or a little get-together with friends. Everyone can relate since we all once were a child.

Who to Ask It To: Ask this question to any of your friends or family member. Your aunt could've been the one who gave you that toy!

15. If you could time travel, when would you go?

Why It's Great: There are so many places and time periods to go from. A question like this can have an infinite amount of answers. It's always interesting to know which period people would first go to.

When To Ask It: Anytime someone talks about what it's like to live in this or that time. Or, you can wait until the conversation talks about time travel itself.

Who to Ask It To: You can ask anyone without needing to have a special relationship with them.

16. What’s your best childhood memory?

Why It's Great: Tapping into childhood memories is a great conversation starter. We normally don't appreciate things when we're kids until we're older. Find out what childhood memory is their favorite to understand their character.

When To Ask It: Throw in this question when you hear a conversation about childhood experiences.

Who to Ask It To: A close friend or lover is the ideal person to talk about this kind of personal question.

17. What’s your pet peeve?

Why It's Great: Whether we like to admit it or not, everyone has a pet peeve that can really get on our nerves. Find out others' pet peeves to make sure you don't accidentally get on their bad side in the future.

When To Ask It: Ask this question to break the ice during a get-together or a family reunion. Know the dislikes of the people close to you to stay on their good side.

Who to Ask It To: People that you want to know better are fair game to be asked this question. Just make sure that you try to remember when they tell you about their pet peeves.

18. What personality trait has gotten you in the most trouble?

Why It's Great: No one is perfect, but there are always things about us that can land us in trouble with others. This question opens up more about one's weaknesses. Learn a thing or two from their stories.

When To Ask It: Topics about self-reflection are rare, especially with a group of friends. However, you can always use this question to start the conversation! Make sure to start with yourself to ensure that the others don't feel pressured to answer!

Who to Ask It To: Tight-knit friends are the ones you want to ask this question. Their advice and perspective can help the most!

19. What is the best piece of advice you’ve received?

Why It's Great: Good advice works best when it’s shared. You never know when another person's advice can change your life. There's a chance that you might also affect another person's life with a single piece of advice!

When To Ask It: Ask this one when talking about your past or things that you have learned over the years.

Who to Ask It To: Role models such as your parents or close friends are excellent choices. You can be sure that they'll never wish you ill-fate.

20. What’s the most beautiful place you’ve ever been?

Why It's Great: The world is full of wonders and experiences. You might find a new location to add to your bucket list after hearing answers from other people. Who knows, it can be your new favorite place!

When To Ask It: Ask this whenever a conversation about travel happens around your group.

Who to Ask It To: Your partner and close friends are perfect for this question. They have a higher chance of going into detail about why that place is beautiful for them.

21. Would You Rather burp every time you lean in for a kiss or drool every time you talk?

Why It's Great: Dating is nerve-wracking enough. If you add these stipulations, then it'll make it almost impossible. However, seeing what others will choose if they have no choice is interesting.

When To Ask It: This question is a fun way to turn a rather boring dating question into something more daring!

Who to Ask It To: It's fun to ask close friends or your partner how they'll react to being forced to choose one over the other.

22. Would You Rather not brush your hair ever or your teeth?

Why It's Great: Some of us already make this choice when we're running late. We've all skipped either brushing our hair or teeth at some point in our lives. But if you have to choose one to skip, that's where the conversation can turn things interesting.

When To Ask It: Ask this during lunch break at work or school. Talking about this will be fun, especially when somebody was late.

Who to Ask It To: Friends or acquaintances you have either in school or work are the best to ask this question.

23. Would You Rather sleep wearing handcuffs or a bike helmet?

Why It's Great: Both situations can be very uncomfortable, but that's the whole point of this question. It's fun to hear the different reasons why someone would prefer one option over the other.

When To Ask It: Random choice questions like this are best done when there's a large group of people to talk.

Who to Ask It To: A large group of friends or family, or else the question won't get much traction for conversation.

24. Would You Rather embarrass yourself at a party or get caught making out with your best friend’s sister?

Why It's Great: This question is entertaining because you have to choose between two hard options. Either one will seriously impact your social life.

When To Ask It: This kind of question is best used during a drinking game or group gathering with a bunch of other people.

Who to Ask It To: Keep this question to only your closest friends. Or else it'll be one awkward conversation with anyone that you're not tight with.

25. Would You Rather be uncontrollably laughing for the rest of your life or uncontrollably crying?

Why It's Great: Everyone you ask this question will either have a quick response or take a long time. Either way, you can be sure to hear a follow-up explanation once they make their decision.

When To Ask It: Random questions like these are great to ask when passing the time with your buddies.

Who to Ask It To: Your friends are your best bet to spend the most time thinking about a solid answer.

26. If you could ask your pet 3 questions, what would they be?

Why It's Great: It would be something if your pet can talk back to you- that would be the craziest thing! Come to think of it, we still ask them questions even though we know they can't talk back. This is good for small talk with other pet lovers.

When To Ask It: When you find yourself in a pet or dog park, you better have some funny questions to ask. They'll come in handy when you want to have small talk with a fellow pet lover.

Who to Ask It To: I bet this won't be the weirdest thing a fellow pet lover has ever heard. They might find the question funny, and you'll leave them with a good impression.

27. What is the funniest thing you have ever seen a stranger do?

Why It's Great: People-watching is the new national pastime. Asking open ended questions like this allows someone to have unlimited responses. That gives you more topics to talk about. Besides, watching other people is like watching a movie slowly unfold.

When To Ask It:The perfect time to ask is when you're just hanging out with your friends or family by the mall. Something entertaining may happen right in front of you. You just have to be observant!

Who to Ask It To: Who's better to ask than your goofy and fun-loving friends and family? Or anybody whose hobby is to observe people.

28. Do you think cats have any regrets?

Why It's Great: Cats are the greatest manipulators of all time. They'll come to you when they want something. And when they're done, they act like they no longer know you. Cats are unique in their own ways, which is why there are many cat lovers out there. It'll be entertaining to talk about cats and how they conspire against humans!

When To Ask It: Ask this when you go to a pet park or cat cafe. Many other pet lovers will find this question funny.

Who to Ask It To: Ask any cat lovers out there. They'd love to share their own theories.

29. How many days do you wear the same pants in a row before it becomes a problem?

Why It's Great: There's no use hiding it. Everyone has worn the same pair of pants more than they actually wash it. But how many times is too enough? That's what you're asking to find out!

When To Ask It: Topics about hygiene or weird habits are perfect when you're having a good time with pals.

Who to Ask It To: Funny questions are best used with people you're close to you. They won't hesitate to share their embarrassing habits with you.

30. Which would be harder for you to give up: coffee or alcohol?

Why It's Great: Which method of self-medicating is most important? For some people, coffee is the most important thing in their morning ritual. But who could resist the temptation of alcohol on Friday nights? This can lead to a hilarious conversation, and I can almost see some debates.

When To Ask It: Ask this funny question during a get-together with your friends in a bar or coffee shop. Make them think of which one they can give up while drinking one of the choices.

Who to Ask It To: The perfect conversation starter to ask friends, colleagues, or family members.

31. Which room in Hogwarts would you most want to have sex in?

Why It's Great: Dirty questions are always interesting cause they'll bring in unique answers from people. Adding Harry Potter locations to the mix only shows how daring some of your friends might be.

When To Ask It: The perfect time to throw in this curveball of a question is when you want to turn the conversation spicy!

Who to Ask It To: Harry Potter fanatics will get a kick out of this question. So make sure to reserve this topic for the biggest of fans to have more interesting results.

32. Do you put the toilet paper roll on the right way or the murderer's way?

Why It's Great: The people you ask this question might not know what the murderer's way is. But if they say they place it inside out, you know there's something weird about them.

When To Ask It: Anytime the conversation goes about habits they make in their homes. Toss in this question to see if anyone puts their toilet paper in the "wrong" way.

Who to Ask It To: The wording of this question might be weird to others. Save this question for those with the same sense of humor as you.

33. What would your perfect Saturday be like?

Why It's Great: Relaxing on a Saturday and doing whatever you want is perfect. However, you might discover that some people like to do specific things to call it a perfect Saturday!

When To Ask It: Talk about this on a Friday to boost people's energy. Remember their answers if you plan to spend weekends with them.

Who to Ask It To: Co-workers or classmates you see regularly are perfect for this question.

34. Which movie sequel do you wish you could erase from history?

Why It's Great: Nothing's worse than seeing something you love destroyed by a poor sequel. Who knows? You might get a good movie recommendation from the people you ask. (Just as long as you avoid the dreadful sequels.)

When To Ask It: Ask this when you need some ideas to watch on a movie night.

Who to Ask It To: Cinephiles are your best choice to ask this question if you want a detailed answer. Of course, you can always ask your friends for their opinions as well.

35. What would your perfect vacation entail?

Why It's Great: Imagining going to your perfect vacation destination is always fun and exciting. It's nice to see how everyone you ask will start to think about what makes them happy the most, even if it's only for a second.

When To Ask It: Vacation planning or even topics about having free time are perfect for a question like this.

Who to Ask It To: You can ask anyone this question from your friends and family. But your partner might appreciate being asked this personal question the most.

Ultimate List of Fun Questions To Ask

Question Categories

Fun Questions to Ask

Sometimes, all you need is a good list of fun random questions to ask that hits on all kinds of topics. They're perfect conversation starters if you want to have  casual small talk.

No matter the context of your conversation, you’ll find a question here to keep things flowing.

  • What’s something that people think makes them look cool but actually has the opposite effect?
  • Have you ever counted your steps while walking?
  • How does someone politely end a conversation with a person who won't stop talking?
  • If you have a million, what are the things you wouldn’t spend?
  • What is the best excuse for being late you’ve heard or used?
  • What is the worst/most annoying catchphrase?
  • What is the best color in the rainbow?
  • What is the best Wi-Fi name you've ever seen?
  • Do you like dipping your Oreo in milk?

Interesting Questions to Ask

Nothing is more awkward than meeting someone and not finding something to talk about.

Small talk will last you a minute or two. You need conversation starters that'll lead you toward a fun conversation. Before you know it, you and your new friend will feel at ease and open, and the conversation will flow naturally.

  • Do you ever sing in the shower?
  • Tell me about the worst pickup line you've ever gotten.
  • What is your favorite celebrity scandal right now?
  • If you were immortal for a day, what would you do?
  • Do you think you’d survive a zombie apocalypse? Why or why not?
  • What weird conspiracy theory do you believe?
  • If animals could talk, which animal would be the rudest?
  • Which Hogwarts house do you belong in and why?
  • If you could talk in your sleep, what would you say?
  • What old person tendencies do you have?
  • What’s the worst thing about peanut butter and jelly sandwiches?

Unique Questions to Ask

Have everyone giggling with these witty ice breaker questions. They're unique for a reason! You might be the first person to ask them these questions. And because of that, you'll probably be an unforgettable companion.

Get everyone feeling friendly with some next-level ice breaker games.

  • Which is better—a novel or a movie?
  • If you could read minds, whose would you want to read?
  • Is soup something you eat or drink?
  • Are you embarrassed of your Google search history?
  • What's the funniest insult you can come up with?
  • If you were told you only had one week left to live, what would you do?
  • Who wins a fight between Superman and Batman?
  • What's your favorite dinosaur?
  • Can you touch your nose with your tongue?
  • What's your cringiest drunken moment?

Fun Questions To Ask Video

99 Fun Questions to Ask - Spark engaging conversations (Animated)

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Downloadable and Printable List of Fun Questions to Ask

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Frequently Asked Questions

How to use fun questions to ask?

You know how important it is to make a good first impression. And there are dozens of fun questions to ensure you’re remembered positively. Even though it’s hard to go wrong with these questions, I have a few tips to help you get the most out of them.

  • Adapt. Even though this list has questions for every scenario, not every question is best for every setting. Choose the questions that make sense for the context you’re in.
  • Listen. If you want people to open up about themselves, you’ll have to show them that you’re listening. Ask follow-up questions and show interest in the person you’re speaking with.
  • Be open. Because fun conversations depend on equal participation. Be prepared to answer your own questions and to share your stories when asked.

What is a playful question?

Playful questions is a fun and casual way of getting to know someone without the pressure of having a  serious talk. The impression that you want to leave is that you're fun, interesting and easy to be with. Funny, random, flirty and weird questions can fall into the category of playful questions.

What fun topics should I ask?

It depends on who you talk to because we all have different definitions of fun. You can start with any of the questions we listed above and see which one sparks their interest. If they keep talking or laughing about that topic, try to focus on that until you learn more about them.

What are fun questions when you are bored?

My favorites are Would you rather questions and Weird questions to Ask. Some of those questions will make you laugh just by hearing them. But what makes it more fun is the potential answers people can give you.

What's the funniest joke you've ever heard?

This is the funniest joke I've heard.

A young wife admonished her husband at a party, "That's the fourth time you've gone back for ice cream and cake. Doesn't it embarrass you?"

"Why should it?" answered her spouse. "I keep telling them it's for you."

It made me laugh hard because I did it in real life! If you want to keep laughing, we have a list of funny jokes to tell a girl you like.

More Awesome Fun Questions to Ask

Looking for even more fun conversations to ask? Check out these great posts.

  1. This or that Questions are best to use when getting to know a new acquaintance. Short and direct to the point but also quirky and funny.
  2. If your conversation is going dry, Weird Questions to Ask will come in handy. It can shake up your small talk to make it interesting.
  3. You should know Interesting Conversation Topics to get a good first impression.