200 Questions to get to know someone

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Whether it’s a coworker, acquaintance, or just someone you want to get to know a
little better, it can be hard to make a connection with people. Not to worry though, I’m
here to help with more than 200 questions to get to know someone.

Questions to get to know someone

• The first set of questions on this page are perfect for getting to know someone you
just met or someone you don’t know well. They are casual yet interesting. If you are
looking to get to know someone even better, you can jump to the next set of
questions.

• The next set of questions is a little more personal or in-depth. You probably wouldn’t
want to ask these questions to folks you just met, but they are perfect for friends you
want to get to know a little better.

• The last few questions are very personal. They are perfect for getting to know
someone you already know well. You can ask them to close friends and people you
are in a relationship with.

Whichever level of question you choose, these 200 questions to get to know
someone are perfect for learning more about someone. Remember to ask follow
up questions to their answers to find out more!

We’ve also got a PDF and an image of all the questions at the bottom of the page!

Casual questions to get to know someone

These questions aren’t too personal and are great for getting to know casual
acquaintances better. But they can also be fun to ask folks you already know pretty
well.

1. What shows are you into?

Probably at least one or two shows they mention will be shows that you’ve seen and
can talk about, and even if not, then you can get them to explain what the shows are
about and what they like about them.
2. What’s your claim to fame?

Most people like talking about themselves, and what better question to get them to
talking than letting them talk about something they are proud of?

3. How often do you play sports?

If they are into sports, this one can be good, but if not, you might want to pass on to
another question.

4. Are you usually early or late?

An odd question, but it can be a good one if you are going to get to know them and
see them again. At least next time you meet you’ll know when to expect them to
arrive. If they are usually early and you are usually late, you might want to make a
special effort to be on time.

5. What quirks do you have?

This is another uncommon conversation question, but it can often tell you a lot about
the person, and it can be a good way to get them talking about themselves.

6. How often do you people watch?

Some people enjoy people watching, others not so much. It often depends on
whether they live in a small town or a big city.

7. What’s your favorite drink?

It can be alcoholic or nonalcoholic, but everyone enjoys talking about the things they
love. And if you ever want to buy them a drink, you’ll know what to get them.

8. What do you hope never changes?

A very open-ended question that can lead to a lot of different types of answers, some
more interesting than others. It all depends on what direction they want to take it.
9. What’s your dream car?

Another question for getting them to talk about what they love and who knows, it may
be a car you’ve also had your eye on, and you can get into a conversation about
cars.

10. Where would you rather be from?

Most people have a special place in their hearts from their hometown, but a lot of
people would rather have been born somewhere else.

11. What songs have you completely memorized?

You probably don’t want to pressure them to sing it unless they’ve got a mind to, but
it will give you a good idea of what type of music they like and can lead easily into a
conversation about music.

12. What would you rate 10 / 10?

Always a great question to get some good recommendations. And most likely some
very good topics for conversation.

13. What job would you be terrible at?

Flipping the common question of their dream job, this question will help you find out
what they think they are not good at or at least what they dislike.

14. What are you absolutely determined to do?

This one looks at some of their dreams or goals and lets you know what they
consider to be a priority in their life. And it can lead to some great conversations
about whatever they are looking to accomplish.

15. What skill would you like to master?

Another question that looks at what they are into or at least what they would like to
get into.

16. What website do you visit most often?

If it’s one that you also visit a lot, you can swap things you found there. If you don’t
really use that site, you can always ask what they like about it.

17. What would your perfect room look like?

Another question that is a little odd but can really tell you a lot about the person.
Their perfect room tells you what their ideal environment is and where they feel most
themselves.

18. What movie title best describes your life?

This one can be a lot of fun, especially if you are both into movies. But if you are at a
loss, there is always IMDB. Lots of funny answers to be had here.

19. What age do you want to live to?

It can get a bit morbid, but it doesn’t have to. Plus, it helps you to see how they view
old age and their place in the world.

20. What kind of art do you enjoy most

Don’t feel limited to what is typically considered to be art, stuff to be put in museums.
Anything that requires creativity can be considered art.

21. What takes up too much of your time?

This will tell you a little bit about what they don’t like to do, and probably a bit about
what they would rather be doing.
22. What do you wish you knew more about?

We all wish we knew more. The subject might depend on the person. But we all have
gaps in our knowledge we’d like to fill.

23. What’s the best way to start the day?

This will definitely tell you a lot about their routines, or at least the routines they wish
they had.

24. What mystery do you wish you knew the answer to?

Will it be a personal mystery? A famous mystery? An unsolved case? Only one way
to find out.

25. How different was your life one year ago?

With this question, you can find out a little about their past, a little about their
present, and probably what they think about how their life is going.

26. What’s the best single day on the calendar?

It could be a holiday, it could be an anniversary, it could be their birthday. Whatever

it is, I’m sure there is a reason why they like it and are probably pretty pumped to tell
you about it.

27. What are some things you’ve had to unlearn?

This is a great way to learn about what misinformation or mistaken beliefs they’ve
had to overcome.

28. What’s your favorite genre of book or movie?

A classic conversation starter, but sometimes those are the best. This is sure to get
them talking about a subject they love, and you might even find you have some
interests in common.
29. What’s the farthest you’ve ever been from home?

We are the same person we were 5 years ago except for the people we’ve met, the
books we’ve read, and the places we’ve been. Time to hear about some of the
places they’ve been!

30. What TV or YouTube channel doesn’t exist but really should?

There are channels of just puppies, fireplaces, and squishing things with hydraulic
presses. What other niche channels haven’t made their way into the world?

31. Where is the most interesting place you’ve been?

Another question that is sure to bring out some interesting travel stories. You might
even get a tip for somewhere to go on your next trip.

32. What fad or trend do you hope comes back?

There are no shortages of fads and trends, now it’s time to find out which old trend or
fad they remember fondly.

33. What city would you most like to live in?

And if they say they don’t like living in cities, you can ask what kind of countryside or
town they would like to live in.

34. When was the last time you climbed a tree just for fun?

Time to see how much of a free spirit they are. As people get older, the number of
trees climbed per year drops at an alarming rate.

35. What do you consider to be your best find?

It could be something they bought, somewhere they went or some amazing

restaurant they ate at. Whatever it is, it’s probably worth checking out or at least
hearing about.
36. What is special about the place you grew up?

Everywhere has something unique, something special about it. It doesn’t matter
whether it’s a person, a place, or a thing, I’m sure there is something about the place
they grew up that they cherish.

37. What age do you wish you could permanently be?

This is a fun question because it leads to some interesting answers, but also, very
often, the age that they pick is usually when they were the happiest. Make sure to
ask what is so special about that age.

38. What’s worth spending more on to get the best?

Whether it’s food, clothing, or something else entirely, this question will get to the
heart of what they value most. Or at least give you an idea of something to upgrade
in your life.

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

Very few people become famous, but everyone has the potential to be. And it
doesn’t necessarily have to be something positive. Lots of people are famous
because they screwed something up.

40. What fictional place would you most like to go?

Books, movies, video games, nothing is off-limits. The fictional world is their oyster.

41. Where is the most relaxing place you’ve ever been to?

Time to do a little digging for great vacation spots! And make sure you ask a lot of
details because I’m sure they will have a lot to talk about.

42. What have you only recently formed an opinion about?

Many people don’t think about how and when they form opinions. So, it’s often
interesting to hear how and why they formed their most recent opinion.

43. What is the most heartwarming thing you’ve ever seen?

Something from reality would be best, but if they can’t think of anything, they can dig
into movies as well.

44. What’s the most interesting piece of art you’ve seen?

It doesn’t necessarily have to be good, because there are a lot of people who aren’t
into art. Just as long as it’s interesting. You might even be able to pull it up on your
phone if they remember enough about it.

45. What’s something you like to do the old-fashioned way?

Sure, modern conveniences are great, but sometimes the old ways are best.

46. Would you rather go hang gliding or whitewater rafting?

This is a good one to judge how into adventure they are and can easily transition into
a good discussion about extreme hobbies.

47. Who has impressed you most with what they’ve accomplished?

We all have people we look up to, finding out who they look up to will let you know
what they consider to be important work, and it makes for an excellent conversation
starter.

48. How do you relax after a hard day of work?

How someone spends their downtime often tells you more about who they are than
what they do for their work.
49. What popular TV show or movie do you refuse to watch?

Whether it’s for moral reasons or they just don’t like the genre, it’s good to know
where they draw that particular line and why.

50. What job do you think you’d be really good at?

There is so much wasted talent in the world from people doing jobs they aren’t well
suited to. Now you can find out what they think they are best at.

51. What pets did you have while you were growing up?

Most people had at least a couple of pets while growing up, even if it’s just a goldfish
or a hamster. Remember to ask follow up questions to keep the conversation going.

52. Where would you spend all your time if you could?

It might be a favorite vacation spot, a favorite bar, or even a movie theater. This
question will tell you a lot about what they enjoy and where they like to spend their
time.

53. What would be the most amazing adventure to go on?

Everyone’s idea of adventure is different. Some people lean to the more extreme,
some to the more mundane. But, however the person you are trying to get to know
leans, you’ll soon find out.

54. What would be your ideal way to spend the weekend?

This is another question that tries to get at what they truly enjoy doing. And everyone
loves talking about things they are passionate about.

55. What’s the best way a person can spend their time?

This simple question can tell you a lot about their world view. The person might say
something like helping the poor, or they might say it’s improving one’s self, or it might
just be having fun. Whatever their answer, it will help you to get to know who they
really are.

56. What one thing do you really want but can’t afford yet?

Everyone has a list of things they would love to have but are a little out of reach.
Always makes for an interesting conversation starter because they already have an
interest in whatever it is.

57. What is the luckiest thing that has happened to you?

While some are luckier than others, we’ve all had a bit of luck come our way. Now
you can find out their good luck stories.

58. What are some small things that make your day better?

It’s the little things that make life worth living, and I’m sure they’ll have plenty to say
about their favorite indulgences.

59. What’s the best thing that happened to you last week?

Always good to keep it positive, and if they can’t think of something specific last
week, feel free to stretch it out to last month or this year so far.

60. What are you looking forward to in the coming months?

Similar to the last question, but this time, we are talking about the future. Find out
what cool plans they have coming up.

61. What’s your favorite piece of clothing you own/owned?

We all have some threads that were exceptionally awesome or held some great
memories, so I’m sure they will too. Hopefully, there will be some stories about the
clothing as well.
62. What is the most annoying habit that other people have?

It’s strange how everyone has certain things that really annoy them. While other
people aren’t bothered by it at all. Now you can find out what not to do around the
person you are getting to know.

63. What game or movie universe would you most like to live in?

This one is a good jumping-off point into what types of media they enjoy. And make
sure to ask them a lot of questions about why they chose that specific universe.
Maybe spin it around and talk about the worst universe to live in.

64. What is the most impressive thing you know how to do?

We’ve all got skills of some sort or another. It doesn’t have to be something jaw-
dropping, just something interesting.

65. What was the best book or series that you’ve ever read?

Great for getting tips for a new book or series to check out but also a good
conversation starter.

66. What question would you most like to know the answer to?

Something big, something small, something personal, or something universal. So

many questions. Whatever they choose, it will definitely tell you a little more about
them and hopefully spark a good conversation.

67. What are you interested in that most people haven’t heard of?

Another one to get some tips for good stuff to check out, and you’ll get to learn
something new about them.

68. Why did you decide to do the work you are doing now?
Whether it’s their dream job or something they just fell into, there is always a story
behind why someone is working in the field they are.

69. What state or country do you never want to go back to?

Traveling is great but every experience can’t be perfect, so what terrible experiences
have they had while traveling?

70. Where do you usually go when you have time off?

It might be a favorite vacation spot or just a spot on the couch. It’s always
enlightening to hear what they do with their time off.

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

It might be something major or something personal, whatever it is, it is probably

something they care a lot about.

72. What is the most annoying question that people ask you regularly?

It might be something based on their looks or accent or a tired and worn out
conversation starter. Let’s hope you haven’t asked it already.

73. If you suddenly became a master at woodworking, what would you make?

This is a pretty off the wall question, but often you’ll get some interesting and
creative answers if you give them enough time to think about it.

74. What could you give a 40-minute presentation on with absolutely no preparation?

Whatever the topic is, they are probably an expert in it. And if they are an expert in a
topic, well, that’s a great thing to know if you are trying to learn more about them.

75. What amazing thing did you do that no one was around to see?
This one can be a bit of a mixed bag. Sometimes they can’t think of anything, but
sometimes it’s something truly amazing.

76. What hobby would you get into if time and money weren’t an issue?

Find out what hobbies they are interested in, and then you can transition into what
hobbies they have now.

77. If you didn’t have to sleep, what would you do with the extra time?

This is an interesting question because even though it seems simple enough, it gets
to the heart of what they truly would like to be doing with their time if given a chance.

78. When people come to you for help, what do they usually want help with?

What problems are the person you are trying to get to know good at solving? Tech?
Fashion? Cars? Something else entirely? Time to find out!

79. What is something you think everyone should do at least once in their lives?

It definitely can be more than one thing, they’ll likely have a few. And it can tell you a
lot about what experiences in their life they consider to be significant.

80. What’s something you’ve been meaning to try but just haven’t gotten around to it?

We all have that list of things floating around in our head that we’ve yet to get to.
Now you can find out what’s on their list!

81. If all jobs had the same pay and hours, what job would you like to have?

Another question that helps you understand what work they feel would suit them
best. It’s a great way to find out what they love to do most.

82. Who’s your go-to band or artist when you can’t decide on something to listen to?
A slightly different take on the classic “What music are you into?” conversation
starter. This one is great for finding out what music is their bread and butter.

83. If you were dictator of a small island nation, what crazy dictator stuff would you do?

Dictators get up to some crazy stuff. With this hypothetical, you can see what
mischief they would get into with nearly unlimited power.

84. What is something that most people consider to be a luxury, but you don’t think you
could live without?

Might be some special brand. Or perhaps some piece of tech. Possibly something
like a massage. There are lots of luxuries out there that we feel like we need.

85. What would be your first question after waking up from being cryogenically frozen for
100 years?

This one can be a lot of fun if the person you are talking to is creative or can just be
a straightforward question. Bit of a hit or miss, but you can give it a shot.

86. What is something that a ton of people are obsessed with, but you just don’t get the
point of?

When everyone is jumping on the bandwagon, where do they draw the line? What
part of pop culture do they choose to opt-out of?

87. If you could turn any activity into an Olympic sport, what would you have a good
chance at winning a medal for?

This is a fun question to find out more about what they are good at. Whether it’s
something silly or something serious, it’ll tell you more about the person you are
talking to.

88. What piece of entertainment do you wish you could erase from your mind so that you
could experience it for the first time again?
A great question for finding out what they really love. Maybe you share their
enthusiasm for that piece of entertainment, or maybe not. But either way, it will tell
you more about them.

89. If you had unlimited funds to build a house that you would live in for the rest of your
life, what would the finished house be like?

Will it be a mansion or something simpler? This is a great question because it tells

you a lot about what they value.

Somewhat personal questions to get to know

someone
This next set is great for people you’ve known for a while and have a pretty good
relationship with but would like to get to know them better.

90. What gets you fired up?

Everyone is motivated by different things. It might be a social cause, exercise, or

money. There are a ton of possible answers to this one.

91. What makes a good life?

There is a ton of philosophy behind this simple question. Sometimes the shortest
questions are the biggest.

92. What risks are worth taking?

Find out how risk-averse they are. Are they willing to take big swings for big gains, or
are they more on the cautious side?

93. What do you take for granted?

We all take things for granted. It’s part of being human. It can be enlightening to see
what they think they take for granted.
94. Who inspires you to be better?

When you find out who inspires them, you find out who their heroes are, as well as
what they aspire to be.

95. What do you have doubts about?

This is a very open-ended question that can lead to some interesting answers.

96. When do you feel truly “alive”?

Chances are what they are doing when they feel truly alive is what they are meant to
be doing, or at least what they love doing. And that is always a good thing to know
when you are getting to know someone.

97. What fact are you resigned to?

Bit of a downer question, so feel free to skip it if you are looking to keep a light mood.
But it can be worthwhile to learn about what bums them out.

98. What book impacted you the most?

They say you are the same person you were 5 years ago except for the places you
been, the people you’ve met, and the books you’ve read. So which books have they
read? Or are they not much of a reader?

99. What’s the best thing about you?

If the person is humble or doesn’t have a lot of self-esteem, it might be hard to get an
answer out of them. But most folks will have an answer, even if they have to think
about it a bit.

100. What would a mirror opposite of yourself be like?

This is another question that is a bit bizarre but can be pretty enlightening. Both for
you and the other person. It’s another way to try to understand one’s self.
101. What irrational fear do you have?

So many phobias. Surely, they’ve picked up at least one irrational one along the long
path of life. Perhaps clowns, the dark, or something more unique, like chickens.

102. What would be your spirit animal?

There’s a good chance you’ll get some lame overplayed ones like wolf, eagle, or
dolphin. But sometimes, when they really think about it, they’ll come up with
something good.

103. What would be the scariest monster you could imagine?

Another one that forces them to be a bit creative. We are all scared by different
things, and their answer can tell you a lot about them or at least what they are afraid
of.

104. What’s the hardest lesson you’ve learned?

Most lessons worth learning are learned the hard way. Now you can find out what
they’ve taken away from their hard knocks in life.

105. What’s something you are self-conscious about?

Whether it’s something to do with their appearance, how they talk, their past, or their
present, almost everyone is self-conscious about something. And sharing
weaknesses is a great way to get closer to someone. Just remember to be
supportive.

106. What is one or two of your favorite smells?

It might be something that reminds them of happier times, or perhaps just a pleasant
smell. Either way, emotion, and memory are linked closely to smell and so there are
probably some memories that they’ll want to talk about after naming some of their
favorite smells.
107. Have you ever given to any charities?

If they have, you can see what kinds of charities they think are worth giving to. And if
they haven’t, at least you know they aren’t the type of person to give to charities.

108. What’s the last adventure you went on?

Big or small, who doesn’t love a good adventure?! And usually, people are excited to
talk about their adventures, which makes it a great question for getting the
conversation going.

109. What are three interesting facts about you?

Sometimes you’ll get people who will rattle off three facts as quick as can be. But the
vast majority of people will take their time and really ponder this question.
Sometimes it can be a bit hard to slip into a conversation casually, but it does make
a good question to get to know someone.

110. What was the best compliment you’ve received?

This one is fun because it lets you know what achievements they are most proud of
and gives you a glimpse into what they might consider to be important in life.

111. What chance encounter changed your life forever?

It’s often been said that life turns on the smallest of chances and seemingly
insignificant occasions. I’m inclined to agree. Now you can find out what small
chances changed their life.

112. What do you want your epitaph to be?

This question can be a bit morbid, but then it can also be pretty enlightening. You
might be able to find out what they view to be important or perhaps how they view
death.

113. What are you really good at, but kind of embarrassed that you are good at it?
Sharing embarrassing things often brings people together, unless it’s really
disturbing and puts you off. But opening up generally is great for getting closer, just
remember not to tease them too much about it or act too grossed out.

114. What is the “Holy Grail” of your life?

What lofty goal do they want more than anything else? Finding out what a person
wants can tell you a lot about them.

115. What do you like most about your family?

Family can be a bit of a touchy subject. But at least with this question you are
keeping it on the lighter side.

116. What do people think is weird about you?

Everyone has their quirks, and sharing them can be a great way to grow closer to
someone and get to know them a little better.

117. What is something you will NEVER do again?

We all make mistakes. They’ve probably learned tough lessons from some of their
bigger mistakes. And who knows, maybe you can learn from their mistakes as well!

118. Who is/was your most interesting friend?

Everyone has at least one friend who is either a bit different or has lived an amazing
life. This one is great for finding out what kinds of stuff the person you are talking to
finds interesting, and to hear some good stories as well.

119. What are you most likely very wrong about?

Just like you, the person you are talking to probably has some doubts about what
they are doing or perhaps even what they believe. And if they don’t, then at least you
know they are the type of person who has no doubts.
120. What’s the most immature thing that you do?

Another question that might help the other person to open up a bit and gives you a
way to show them that you aren’t going to judge them.

121. What stereotype do you completely live up to?

It’s hard to buck all the stereotypes. There are a lot of stereotypes out there, and
chances are some of the ones that are aimed at you hit the mark. The person you
are talking to is probably in the same boat. Embrace some of the lighthearted or
positive stereotypes and have a laugh about them.

122. What is the biggest lesson you NEVER learned?

Another question that can tell you a lot about a person and what they value, or at
least how stubborn they are.

123. What dumb accomplishment are you most proud of?

This question can be a lot of fun. We’ve all done a lot of ridiculous things in our lives
and some of them we can be proud of, even if they might not be the most prestigious
accomplishments.

124. What was the most memorable gift you’ve received?

Lots of possible answers to this one. Everything from something extremely

thoughtful, to childhood presents, to ridiculously generous presents.

125. What chapters would you separate your autobiography into?

This is a great question to lead you into a discussion about their and your own past
and how each of your pasts has shaped you into the person you are today.

126. What do you hope your last words will be?

Sure, it might be a bit morbid, but it makes for a conversation question that they’ve
probably haven’t heard before. And a lot of times you’ll get some really interesting
answers.

127. What do you spend the most time thinking about?

I love this question because it gets to the heart of what the person is most occupied
with. It could be work, a hobby, insecurities, or any number of things. Whatever their
answer is, it will tell you a lot more about the person.

128. What is something you can never seem to finish?

We all have a seemingly never-ending to-do list. Find out what is on theirs. Or
perhaps they’ll take it in a different direction and talk about books, movies, or games
half-finished.

129. What mistake do you keep making again and again?

We all make mistakes, and most of us make a select few again and again. A lot of
times there will be a few you have in common and you can commiserate together.

130. What’s the best thing you got from your parents?

It might be something physical, it might be money, it could be a lesson or even just

genetics. Whatever it is, it can tell you a lot about what they value and find to be
important.

131. What is the strangest thing you have come across?

This one is great because you never know what they’ll answer with, and however
they answer this question, it’s bound to be interesting.

132. If you could make a 20-second phone call to yourself at any point in your life present
or future, when would you call and what would you say?
I love this question because there are so many possible answers, and so many
different directions this question can be taken. Maybe it would be something to make
money or avoid a mistake, or something completely off the wall.

133. What’s the best and worst thing about getting older?

We are all getting older. Find out what they are dreading, and what they are looking
forward to, and see if it matches up to your own thoughts.

134. If you could have a never-ending candle that smelled like anything you wanted, what
fragrance would you want it to be?

This one is mostly a fun thought experiment, but hey, they can’t all be serious right?
What would be the fun in that?

135. What is something you are certain you’ll never experience?

It might be something that is totally against their nature or perhaps something that
they think will never happen. But whatever it is, make sure to ask lots of follow up
questions about why they chose that one.

136. What challenging thing are you working through these days?

This question borders the very personal line, so if you want to save it for when you
know them better, feel free. But if you do decide to ask this question just listen with a
sympathetic ear don’t try and give them solutions unless they ask for them.

137. What’s one responsibility you really wish you didn’t have?

The older we get, the more responsibilities we seem to accumulate. Find out which
ones they wish they could shrug off with this question.

138. What do you wish your brain was better at doing?

Whether it’s math, being creative, being social, or whatever, we all wish our brains
were a little better at doing one thing or another. Just remember if your brain isn’t
performing how you want it to, you can train it, the brain is a wonderfully malleable
organ!

139. If your childhood had a smell, what would it be?

Memories are linked so closely to smell. I bet if you start playing back some
childhood memories, you might remember some of the smells from your childhood. If
not, you can always get creative and guess at the smell.

140. In your group of friends, what role do you play?

Which one are you and which one are they? The planner, the responsible one, the
crazy one, the funny one, the quiet one, the smart one, the driver, or do you fill a
different role? Either way, the role a person plays with their friends can tell you a lot
about the person.

141. Which of your scars has the best story behind it?

A lot of scars have some good stories behind them, and everyone loves swapping
stories!

142. What have you created that you are most proud of?

It can be something big, something small, something physical, or something

immaterial. But everyone has something they are proud of if they think hard enough
about it.

143. What do you strongly suspect but have no proof of?

This is another question that can be taken in a lot of different directions. Whether
mundane or profound, it’s always interesting to hear someone’s answer to this
question.

144. What were some of the turning points in your life?

Sometimes life turns on a seemingly insignificant decision, and sometimes it’s a
decision that we know will change our lives forever. Sometimes it’s not our decision
at all, but life or the people around you blindsiding you with something that changes
your life forever.

145. What bends your mind every time you think about it?

While the vastness of space is a popular answer to this one, you never know what
kind of interesting thing the person you are talking to might come up with. And why
waste the chance to go “whoa.”

146. What’s the title of the current chapter of your life?

This answer depends a lot on their current mood and how they are looking at the
world at that moment, but it’s good to know what they are going through.

147. Among your friends or family, what are you famous for?

Perhaps an amazing talent? Maybe a unique character trait? Possibly even

something that isn’t true. Whatever the answer, it’s sure to be something fun to
discuss.

148. What is something that your friends wouldn’t believe was true about you?

Often a person’s reputation doesn’t completely live up to reality. Find out what their
friends think about them and what the real story is.

149. What’s something horrible that everyone should try at least once?

It could be a food, activity, place, or something completely different. Whatever it is

they choose, it’s bound to be interesting.

150. If you had a personal flag, what would be on it?

I like this one because it forces you to think outside the box. It also tells you a lot
about the person’s aesthetic and probably a little about their personality or what they
value.

151. If your life was a book, what would its title be?

Another one that is more entertaining the more creative you get with it. It can be a lot
of fun trading titles back and forth and discussing why you chose the title you did.

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

Who doesn’t love a good post-apocalyptic story! And what they think they would do
can tell you about their personality and what they think is important.

153. What stats for your life would you most like to see?

It can be anything. Steps walked. True loves passed on the street. Percentage of the
World seen. You can get as creative as you want with this one.

154. What did you think you would grow out of but haven’t?

It might be something positive that they are happy they held onto or perhaps a
negative habit that has persisted. Whatever they come up with will probably tell you
something about who they are now and possibly who they want to become.

155. What are three of the most significant numbers in your life?

This one is great because it’s a fun and creative way to learn more about the person.
I would suggest they tell you the number, and you guess what it refers to, but there
are way too many ways that could go wrong. So, steer clear of that little game.

156. What are some of your personal “rules” that you never break?

Everyone has rules for themselves that they try to follow. Find out which ones they
follow most diligently.
157. What’s the best and worst piece of advice you’ve ever received?

A great question to ask because you might just pick up some excellent advice. And
it’s always good to ponder previous advice you’ve been given as well.

158. What song or artist do you like but rarely admit to liking?

Ah, the guilty pleasure songs or artists. We all have some songs or artists that are so
cheesy or cringe-worthy that we are a little embarrassed that we like them. But I say
embrace them!

159. What annoys you most about the in-groups you are a part of?

A lot of people don’t really think of the in-groups they are a part of and how they
affect their lives and beliefs. Some examples of in-groups you might be in: a country,
a political party, a school, a fan of a sports team, a religion, a club, a race, a follower
of a hobby, a watcher of a TV show, etc. There are so many in-groups that we all are
a part of.

160. What small gesture from a stranger made a big impact on you?

It could be a kind word, a kind gesture, a piece of advice, or something else entirely.
And just remember, you can be that stranger that has a big impact on the lives of
others.

161. What do you regret not doing or starting when you were younger?

It can be interesting to talk about paths not taken and what might have been. And we
all wish that our earlier selves did something to improve our current self. Just
remember that in 5 years you’ll be looking back and wishing you had started
something. As they say, the best time to plant a tree was 10 years ago, but the
second-best time to plant a tree is today.

162. What’s the dumbest thing you’ve done that actually turned out pretty well?

You always have to love when you stumble into a good outcome after a bunch of
bad decisions. Sure, it doesn’t happen often, but when it does, it’s always satisfying.
163. If you had to change your name, what would you change it to?

The trick to this question is the “had to,” most people would just prefer to keep their
name. But it’s always interesting to hear what they would choose if they couldn’t
keep their current name.

164. When people look at you, what do you think they see/think?

I like this question because by explaining the gap of how they think the world views
them versus what they are really like, you get to learn a lot about them.

165. What can you not get right, no matter how many times you try?

A lot of times, we have something that we’ve tried and tried, but whether it’s from
lack of commitment or outside factors, we just can’t seem to nail it.

166. What question can you ask to find out the most about a person?

This is another question that I love because you learn something about them from
the question they choose to ask. And when you answer their question, they learn
more about you.

167. As you get older, what are you becoming more and more afraid of?

It’s odd how fears change when you get older. You slowly lose your fear of some
things while others take their place.

168. What lifestyle change have you been meaning to make for a while now?

No need to wait for New Year’s, any time is a great time to make a resolution. Find
out what some of their personal goals are and share some of your own goals as well.

169. In what situation or place would you feel the most out of place?
By talking about where they feel most out of place, you can often tell what kind of
place they feel most comfortable in. And if you can’t, well, that can be your next
question!

170. There are two types of people in this world. What are the two types?

Yes, I know there aren’t two types of people in this world. But it can be a lot of fun to
come up with examples. Even if there are always exceptions and you can’t truthfully
generalize like that, it can still be a fun question to answer.

171. What personality trait do you value most, and which do you dislike the most?

It’s funny how different people have different personality traits that they hate more
than others and other traits that they admire more than others. It’s almost like we
each are social puzzle pieces designed to appeal to some people and not to others.

172. When was the last time you changed your opinion/belief about something major?

This question is great for seeing how likely they are to change their opinions or
beliefs once they’ve settled on them.

173. What would you do if you knew you were going to die in one day?

This is a great one to ask yourself or others. It’s a great way of putting life into
perspective and letting you know what is important in your life to you.

174. What are some of the events in your life that made you who you are?

There’s no doubt that the events we’ve experienced have a huge effect on who we
are and how we view the world. It’s always good to know what kind of events shaped
the person you are talking to and how they chose to view those events.

175. If life is a game like some people say, what are some of the rules?
This can turn into a really long, fun discussion about the hidden rules that we all live
by. You can take it in a serious or a more playful direction, both are fun and
rewarding.

176. They say that everyone has a book in them. What would your book be about?

Fiction, non-fiction, autobiography, textbook? What kind of book do they think they
would like to put out into the world?

177. What could you do with two million dollars to impact the most amount of people?

The focus here isn’t necessarily impacting them positively or negatively, more about
the sheer volume of people. Could you do something that impacted every person on
the planet?

178. What would be some of the most annoying things about having yourself as a
roommate?

I love this one because it forces you to look at some of the less pleasant aspects of
your personality that you might not normally think about.

179. What do you want to be remembered for?

Very similar to the epitaph question, but while that question was more the short and
sweet version, this one is great for elaborating on what they think of as a good life.

180. If you could make one rule that everyone had to follow, what rule would you make?

Will it be something altruistic? Something selfish? Something silly? Only one way to
know!

181. What’s something that happened or something that someone said that changed how
you view the world?
As we get older, the way we view the world shifts and changes. Sometimes it’s
gradually and sometimes suddenly. Find out how they view the world by finding out
what changed that view.

182. If you were put into solitary confinement for six months, what would you do to stay
sane?

This question might let you know a little bit about how much they need social
interaction, it might also give you a clue into what brings them peace or purpose.

183. If you could have a video of anyone event in your life, what event would you choose?

I love this one because it is so open-ended. It can be any event big or small. It could
be something momentous you don’t want to forget, or it could be to answer a long-
standing question about the event.

184. What incredibly strong opinion or belief do you have that is completely unimportant in
the grand scheme of things?

I mean, I guess you could say no opinion or belief is important in the grand scheme
of things, but let’s not get nihilistic here. This question is more about putting opinions
or beliefs into perspective.

185. What are the top three things you want to accomplish before you die? How close are
you to accomplishing them?

This one is a big question that everyone should probably ask themselves. And the
person you are talking to might not have an answer, but it’s also fun and enlightening
to brainstorm about possible things you both want to accomplish before you die and
try to narrow it down to three.

186. If you could convince everyone in the world to do one thing at one point in time, what
would that thing be?

Give them time to think about this one, it’s more interesting the more creative you get
with it. You could go in all kinds of different directions with this one.
187. If you had a clock that would countdown to any one event of your choosing, what
event would you want it to countdown to?

Most people will probably say their death. But some people don’t want to know when
they’ll die. You can also get pretty creative with it. When will humans colonize
another planet? When will you find the person you’ll marry?

188. What do you wish you could tell yourself 10 years ago? What do you think you’ll want
to tell your current self 10 years from now?

Similar to the question about what you regret not starting when you are younger, but
this one is a little more in-depth. Feel free to skip this one if you covered enough
regret ground in the earlier question.

189. If you were forced to relive one 10-minute block of your life again and again for all
eternity, what 10 minutes of your life would you choose?

Sometimes our lives spin on moments, and sometimes in those moments, we make
mistakes. What would be great to take back control of and fix the error you made.

Very personal questions to get to know someone

better
These questions can lead to some deep, sometimes painful discussions. Best to
save these questions for when you are both ready for a more serious discussion.

190. Have you ever saved someone’s life?

This one is a bit hit or miss. Most people haven’t. But if they have, it’s probably a
pretty impactful moment in their life. Just make sure they are comfortable talking
about it.

191. What are you addicted to?

While we all are addicted to something, some addictions are way more harmful than
others. So, you might want to be a bit wary about this question. It can easily slip into
dark places or it might not be something they want to talk about.
192. What keeps you up at night?

Existential dread? Daily stresses? Irrational fears? Internal chatter? All kinds of dark
avenues to turn down with this question.

193. What lie do you tell most often?

We all lie to ourselves; the trick is knowing that we do and spotting the lies. Hearing
the lies they tell themselves might help you face the lies you tell yourself.

194. What do you regret not doing?

We all have regrets, some of us have more than others. Some are small, and some
are life-changing. But what matters is if you can let go of them or do they still haunt
you? And just remember most people regret more the things they didn’t do than the
things they did do.

195. What gives your life meaning?

This is a pretty big question for all of us. It might be family, work, hobbies, or religion.
Or something else entirely. Whatever it is, it is sure to play a big part in who they are.

196. What are you most insecure about?

Our insecurities can be one of the hardest things to talk about and even harder to let
go of. If the person is being honest with you, tread carefully, it’s some emotionally
unsteady ground.

197. What bridges do you NOT regret burning?

Everyone talks about how they wish they hadn’t burned this bridge or that. But who
are the people they are glad that they cut out of their life?

198. What’s the most illegal thing you’ve done?

This one can often lead to some funny stories or some decidedly unfunny stories. It’s
a bit of a mixed bag, so I put it in the very personal section just to be safe.

199. How do you get in the way of your own success?

This is another question that can cut deep. A lot of people sabotage themselves
when they start doing well. And the reasons why they do are often deep-seated and
primal. Or sometimes, it’s just a personality trait.

200. What are you afraid people see when they look at you?

This is another question that attempts to get at deep-rooted insecurities but in a

roundabout way. It can be pretty effective in bringing out insecurities we didn’t even
know we had.

201. What’s the most surprising self-realization you’ve had?

This is another question that can go positive or go dark, and there is really no way of
knowing which way it will go. So, I decided to tuck it in this section just to be safe.

202. How do you hope you’ll change as a person in the future?

I like this question because it’s a positive way of talking about shortcomings. It
focuses more on improvement rather than just the bad side.

203. What’s one thing you did that you really wish you could go back and undo?

Another question that is all about regret. But it can be rewarding to think back on
what we regret and how we would do it differently now. It helps us make better
decisions in the present.

204. What do you most often look down on people for? What do you think other people
look down on you for?
This is a negative question in general, but it can help people realize their prejudices
and hopefully examine them and see if they hold up to scrutiny or if the prejudices
are just things sticking around because they haven’t been examined.