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, scrub every inch of your body before a first date, and freak out before meeting her parents the first time.

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

When you enter a novel situation with a stack of interesting questions to ask you allow the people you meet to talk about their favorite subject: themselves.

Asking a person questions about him or herself is an even better way to make a positive first impression than directing their focus on your own charm or sociability. Make use of these fun questions to help new people open up, feel comfortable, and walk away remembering how good you made them feel.

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


10 Fun Conversation Starting Questions to Ask

There’s nothing more awkward than meeting someone new and panicking to find something to talk about.

Small talk will last you a minute or two, but what you need at that moment are conversation starters that will lead you towards an fun, fascinating conversation. Before you know it you and your new friend will feel at ease and open, and the conversation will flow naturally.

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

On either end of the scale, parents are a great source of stories.

2. Who was your worst teacher? Why?

Bad teachers are the stuff of nightmares.

3. Who was your favorite teacher? Why?

Great teachers can change a student’s life forever.

4. What was your favorite toy growing up?

Childhood toys keep their sentimental value for life.

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

First stop: wherever Mary McFly got his Nike’s.

6. What’s your best childhood memory?

Tapping into childhood memories is a great conversation starter.

7. What’s your pet peeve?

People can be annoying, but venting helps.

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

Everyone has a natural tendency that has caused them trouble in the past.

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

Good advice works best when it’s shared.

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

Some names seem to fit certain personalities.

10 Best Fun Questions to Ask

What are some fun questions to ask? Well, the best fun questions to ask all have a few things in common: they focus on positive ideas and memories, they are great segues for fun stories, and they show your interest in the person you’re speaking to.

Use these questions next time you’re with someone riding in the car, sitting down to lunch, or grabbing drinks.

11. What accomplishment are you most proud of?

Everyone loves a chance to brag a little bit.

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

A person who can recognize greatness in others is the type of person you want to keep around.

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

This is a great way to begin a conversation about travel.

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

All societies needs both types.

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

Moments of true courage are rare and inspiring.

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

Everyone needs a feel-good ritual.

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

Which method of self-medicating is most important?

18. What is your favorite Wikipedia article?

No matter what your teachers said, Wikipedia is the ultimate collection of mankind’s knowledge.

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

It might be time to try out that old favorite again.

20. Can I get you another drink?

Everyone’s favorite question.

5 Fun Would You Rather Questions

Would you rather questions are like the multiple choice section of a test. You still have to think about your answer, but you have options to choose from.

The best thing about these questions is that there’s no wrong answer, and the questions are all fun.

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

Either way, good luck in the dating scene.

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

Some of us already make this choice when we’re running late.

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

I guess the answer depends on what else happens in bed.

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

Either one will seriously impact your social life.

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

Laughter requires less clean up but can land you in hot water in the wrong setting.

7 Incredibly Funny Questions to Ask

There’s something about funny people. They’re magnetic. They lift the moods of everyone around them. They make great first impressions.

Whether you’re a naturally funny person or someone who’s comedic skills could use a little work, this list of funny questions to ask will draw smiles and laughter from your conversational partners and endear you to them from the very first encounter.

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

You always ask who’s a good boy, but what about how’s a good boy?

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

People watching is the new national pastime.

28. Do you think cats have any regrets?

Do those jerks have any remorse?

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

Pants: the napkin you wear.

30. What are your movie theater popcorn habits?

How many previews before you need a refill?

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

What happens in the Chamber of Secrets stays in the Chamber of Secrets.

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

Yes, there is a right way.

10 Fun Questions to Ask a Girl

There is a time for deep questions, there is a time for serious discussions, but there is also a time for fun.

This list of fun questions to ask a girl is designed to keep things your interactions with the ladies light and interesting.

They’re the type of questions that are answered with a laugh and that light touch on the arm that lets you know things are going well. Pick your favorites from this list before a night on the town or a date with your lady and be prepared for sparks to fly.

33. What would your perfect Saturday be like?

Take notes and plan accordingly.

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

Sequels are notoriously disappointing.

35. What would your perfect vacation entail?

Mountains, beaches, or exotic lands?

36. What’s a great book you’ve read recently?

Literary tastes are a good signal of personality traits.

37. What’s the one food you could never bring yourself to eat?

Remember the show Fear Factor?

38. What’s your dream job?

Imagine money wasn’t an issue, what would she want to be doing?

39. Cake or pie?


40. Who is the kindest person you know?

Just thinking about the person is likely to put a smile on her face.

41. What fictional character do you wish you could meet?

It’s amazing how much a made up person can impact real life.

42. What’s the first thing you do when you get home from a trip?

After kicking off her shoes, of course.

10 Fun Questions to Ask a Guy

Men’s minds work differently than women’s. We can argue whether or not that’s a good thing, but the truth is that we tend to think about different things in different ways.

What are some fun questions to ask guys? Well, the following list of fun questions to ask a guy is designed to hit the topics that men think and talk about and is sure to come in handy whether you’re meeting someone new or hanging out with the crew.

43. What was the funniest way that you have been injured?

Goofy injuries are just part of being a man.

44. If your life was a movie, what songs would be on the soundtrack?

This question will tell you about his musical tastes and personality.

45. What TV catch phrase do you most enjoy using?

Catch phrases may be a thing of sitcoms past, but they’re still hilarious.

46. What terrible movie do you love?

There’s a certain pleasure to be found in awful movies.

47. What song do you have to sing along with when you hear it?

Get the answer and find a karaoke bar, stat!

48. What game are you really good at?

Drinking games, card games, board games… everyone excels somewhere.

49. Which movie do they need to make a sequel to?

So many great movies have left us wanting more, what would he like to see?

50. What’s the right age to get married?

It’s amazing how much the answer will change from person to person.

51. What’s your favorite childhood book?

Berenstain Bears conspiracy aside, those books were great.

52. If you could choose your own nickname, what would it be?

People usually have no say in their nicknames, give him the power to choose his own.

7 Fun Questions to Ask to Get to Know Someone

Getting to know someone, to really know them, can be a challenge.

It’s a process that requires time and dedication, but as you know from the close relationships you already have, getting to know people is worth the effort.

These get to know you questions are a fun, easy way to set off on the path towards friendship. Just because it takes some effort, doesn’t mean it can’t be fun.

53. What are your 3 favorite movies?

Shared taste in movies is a surprisingly good basis for a friendship.

54. If you had to live in a different state, what would it be?

Every state has something to offer, it just depends on what you’re looking for.

55. As a child, what did you wish to become when you grew up?

So few people actually become what they wanted to be, but it’s fun to reminisce.

56. What extracurricular activities were you involved in during high school?

This question will give a quick peek into what someone was like in the most awkward time of life.

57. Are you spiritual or religious in any way? If so, how?

Spirituality can be central to a person’s identity.

58. Do you think of yourself as being naughty or nice?

The price of fossil fuels is going down, but some people embrace the naughty lifestyle anyways.

59. Are you old-fashioned?

This question is pretty broad, let them interpret however they choose.

9 Fun questions to ask a new friend

Asking questions to your new friend shouldn't feel like an interview. You should also have some fun questions to ask a new friend to give a more relaxed environment for your friend.

60. What songs have you completely memorized?

And then get ready for them to sing the whole song.

61. What movie title best describes your life?

Would it be as dramatic as The Notebook or as crazy as The Hangover?

62. As the only human left on Earth, what would you do?

There are endless possibilities as to what they can do as the only person on Earth. This is definitely a fun question to talk about.

63. What is one of your favorite smells?

With the abundance of smells in the world, it's impossible not to choose one.

64. Ever tried putting a bunch of glue on your palm and then peeling it off?

The real question is... who hasn't?

65. If you had to change your name, what would your new one be?

You might get some ideas on what to name your kid in the future.

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

Let them share it with you. It might be the funniest one you'll ever hear, too.

67. Who would you trade places with someone for a day and why?

If you want a fun question, this one should be in your options. Dive into why one person's life is so interesting to live.

68. Do you love pineapples on pizza?

The never-ending debate.

9 Fun, Random Questions to Ask

This list of fun random questions to ask hits on all kinds of topics.

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

69. If you could have dinner with anyone from history, who would it be?

History is full of people who would make great dinner dates.

70. Who would play you in a movie of your life?

Be sure to ask if that casting decision is based on appearance or personality.

71. If you could shop for free at one store, which one would you choose?

Whether the person chooses pragmatically or

72. What’s the worst thing you did as a kid?

We do terrible things before we know better, and those things make great stories.

73. If you could marry a fictional character, who would it be and why?

Everyone has fallen for someone who doesn’t actually exist.

74. What television show do you plan your day around in order to see it live?

We live in the golden age of TV

75. Which is better—a novel or a movie?

Both mediums offer something that the other can’t.

76. If you could read minds, whose would you want to read?

The girl at the coffee shop? The boss at work? So much snooping to do!

77. If you were told you only had one week left to live, what would you do?

What dreams would he or she fulfill with that ultimate motivating factor?

7 Fun Interview Questions

When you're choosing candidates for your team, you'll need some fun interview questions to go along with the regular interview questions.

78. What's something that's true that almost nobody agrees with you on?

We all have something we take seriously and believe in strongly and it's the rest of the world that needs to wake up to our brilliance.

79. If you were starting a company tomorrow, what would the top 3 core values for your company be?

How well can the candidate articulate their core values?

80. How do you feel about sharing your password with your partner?

This would depend on the kind of information that's available behind the passwords and how balanced the partner is and the level of trust the two individuals feel safe cultivating for each other.

81. Do you judge a book by its cover?

Don't we all? And don't we feel better to know exactly how others do?

82. If a genie granted you 3 wishes right now, what would you wish for?

Wildest dreams or practicalities? Selfish wishes or Manifestations for the world and ending suffering? This shows how far outside of their own survival your candidate is willing to consider.

83. What’s something that people think makes them look cool but actually has the opposite effect?

How strong is your candidate's sense of irony and ability to choose authenticity over masking? If someone's trying for cool and it's backfiring there's definitely some masking and insecurity going on. Can the candidate sniff those things out?

84. How does someone politely end a conversation with a person who won't stop talking?

Tact is one of the most valuable talents out there.

10 Fun Ice Breaker Questions

Get everyone giggling with these witty ice breaker questionsGet everyone feeling friendly with some next-level ice breaker games.

85. What wastes the most time in your day to day life?

A person's boundaries around time-wasting say a lot about their emotional burdens and self-discipline. On the other side, what's considered a waste of time by one person is not for another. And some people are really hard on themselves and consider self-care a waste of time because they struggle to value themselves.

86. Why do they call them "Free Gifts"? Aren't all gifts free?

There's an oxymoron to wade through like quicksand and taffy. Hopefully, the answerer enjoys this sort of quandary.

87. If a criminal turns himself in, shouldn't he get the reward money?

This is a gauge for compassion. Many criminals aren't inherently bad. Wouldn't everyone who can't get employment fast enough or due to discrimination be driven to steal in order to provide for their child whom they love?

88. Why does a round pizza come in a square box?

If you've seen the octagonal shaped boxes that some pizzas come in, you'll notice they're more complicated to construct than a square box...

89. Do they bury people with their braces on?

This brings up how most people braces aren't of typical age for dying which makes this question kind of sad actually.

90. Why is the man who invests your money called a broker?

What exactly has broken here?

91. Why are dogs noses always wet?

Do they come up with something witty or do they go the nerdy science route?

92. Can you cry underwater?

Has a tree still fallen if nobody hears it crash?

93. How old are you before it can be said you died of old age?

Is old age a cop-out? Does it just mean there was no ravaging disease present?

94. If I had my legs amputated, would I have to change my height and weight on my driver's license?

With prosthetics available, this is an interesting question.

5 Fun Never Have I Ever Questions

If you're ever hanging out and connection reaches a lull, you might want to play the game, never have I ever questions.

It's sure to create space for everyone to feel good sharing.

95. Never have I ever tasted cat food

The good quality organic stuff is no different than canned meat for people although not everyone realizes that.

96. Never have I ever believed there was a ghost under my bed

You'll get an idea of how anxious they were as a kid.

97. Never have I ever eaten something past its expiration date

Those dates are just for legality's sake. If you want to know whether food is good or bad to eat, smell it. Duh.

98. Never have I ever tasted Himalayan salt

Not sure why this pushes people's edge, but this salt is pink, and beautiful and has healing properties.

99. Never have I ever eaten anything uncooked

Salmonella is serious, but there's a lot of paranoia around it.

How to Use Fun Questions to Ask

You know how important it is to make a good first impression, and you now you know dozens of fun questions to ask in order to ensure that 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.

1. 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.

2. 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.

3. Be open

Fun conversations depend on equal participation. Be prepared to answer your own questions and to share your stories when asked.

Downloadable and Printable List of Fun Questions to Ask

Here is a downloadable and printable jpg/pdf list of fun questions to ask (right click the image and select Save Image As...):

More Fun Questions to Ask

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

  1. This or that Questions - Lightning round questions that lead to fun questions.
  2. Weird Questions to Ask - Sometimes you just gotta get weird.
  3. Interesting Conversation Topics - The Dos Equis guy approves.

In Conclusion

Meeting new people can be intimidating, especially if you don’t come prepared with fun questions to ask the people you strike up conversations with.

Keep this list of 90 Fun Questions to Ask handy and you’ll have the ultimate resource to make a great first impression, be it with new friends or new romances.