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21 Questions to Get to Know Someone

All-purpose conversation starters for anyone

One set that works on everyone: a new friend, a first date, a coworker at the team lunch. These move from easy favorites to values and stories, so the conversation deepens on its own.

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21 Questions
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Question #1

What is the story behind your name?

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All Questions

105 questions
#1
easy

What is the story behind your name?

Follow-ups: Who chose it? • Do you like it?
#2
easy

What is one thing most people get wrong about you?

Follow-ups: Why the mix-up? • Do you correct them?
#3
easy

What is your favorite way to introduce yourself?

Follow-ups: Why that way? • What do you leave out?
#4
easy

What is the best part of your typical day?

Follow-ups: Why that part? • What ruins it?
#5
easy

What is one thing you could talk about for hours?

Follow-ups: Where did it start? • What is your hot take?
#6
easy

What is a small pleasure you never get tired of?

Follow-ups: Why does it work? • When did you last enjoy it?
#7
easy

What is the most interesting place you have ever been?

Follow-ups: Why there? • Would you go back?
#8
easy

What is one thing you are oddly good at?

Follow-ups: How did you learn it? • Have you shown off?
#9
easy

What is one thing you are hilariously bad at?

Follow-ups: How bad are we talking? • Do you avoid it?
#10
easy

What is your favorite question people ask you?

Follow-ups: Why that one? • What is your standard answer?
#11
easy

What is a question you wish people asked you more?

Follow-ups: Why that one? • Answer it now?
#12
easy

What is the best year of your life so far?

Follow-ups: Why that year? • Could it happen again?
#13
easy

What is one thing you are looking forward to right now?

Follow-ups: Why that? • When is it?
#14
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What is a habit you have that you think is rare?

Follow-ups: Where did it come from? • Would you recommend it?
#15
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What is your favorite smell in the world?

Follow-ups: Why that smell? • What memory does it unlock?
#16
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What is one thing that instantly makes you feel at home?

Follow-ups: Why that? • Where is home right now?
#17
easy

What is the best gift you have ever received?

Follow-ups: Why did it land? • Who gave it?
#18
easy

What is the best gift you have ever given?

Follow-ups: Why did it work? • What was their reaction?
#19
medium

What is one thing you changed your mind about this year?

Follow-ups: What changed it? • Was it hard?
#20
medium

What is something you are certain you will never change your mind about?

Follow-ups: Why so sure? • Has it ever been challenged?
#21
easy

What is your favorite thing about your best friend?

Follow-ups: How did you meet? • Do they know?
#22
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What is one thing you and your family have in common?

Follow-ups: Is it a good thing? • Who has it most?
#23
easy

What is one thing you are the complete opposite of your parents in?

Follow-ups: Why the difference? • Is it for the better?
#24
easy

What is the most important lesson your family taught you?

Follow-ups: Who taught it? • Do you pass it on?
#25
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What is one tradition you hope you pass on someday?

Follow-ups: Where did it start? • Who gets it next?
#26
easy

What is your favorite memory from school?

Follow-ups: Why that one? • Who was there?
#27
easy

What is one subject that changed how you think?

Follow-ups: Why that subject? • Who taught it?
#28
easy

What is the best trip you have ever taken?

Follow-ups: Why was it the best? • Who came with you?
#29
easy

What is one place you never want to visit again?

Follow-ups: What happened? • Was it that bad?
#30
easy

What is your dream trip that you have not taken yet?

Follow-ups: Why has it not happened? • When is it?
#31
easy

What is one food you think everyone should try once?

Follow-ups: Why that food? • Where is the best version?
#32
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What is one food you will never understand the hype about?

Follow-ups: Why the hate? • Have you tried it enough?
#33
easy

What is your go-to order at a restaurant?

Follow-ups: Why that order? • Do you ever switch?
#34
easy

What is one meal you could eat forever?

Follow-ups: Why that meal? • What is the drink?
#35
easy

What is your favorite thing to cook?

Follow-ups: Why that dish? • Who is your taste tester?
#36
easy

What is one thing you refuse to cook?

Follow-ups: Why the refusal? • Who cooks it for you?
#37
easy

What is your favorite book that you recommend to everyone?

Follow-ups: Why that book? • Has anyone read it?
#38
easy

What is one movie that everyone should see once?

Follow-ups: Why that movie? • What is the takeaway?
#39
easy

What is a show you finished in one weekend?

Follow-ups: Why could you not stop? • Was the ending worth it?
#40
easy

What is one song that always gets you moving?

Follow-ups: Why that song? • Where do you dance to it?
#41
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What is your favorite lyric of all time?

Follow-ups: Why that line? • What song is it from?
#42
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What is one album you would take to a desert island?

Follow-ups: Why that album? • What is track one?
#43
easy

What is your favorite podcast or radio habit?

Follow-ups: Why that one? • When do you listen?
#44
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What is one thing you listen to that would surprise people?

Follow-ups: Why the surprise? • Do you hide it?
#45
easy

What is your favorite way to exercise or move?

Follow-ups: Why that? • When do you do it?
#46
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What is one sport you love watching?

Follow-ups: Why that sport? • Who is your team?
#47
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What is one sport you would love to try?

Follow-ups: Why that one? • What is stopping you?
#48
easy

What is your favorite outdoor activity?

Follow-ups: Why that? • Where do you do it?
#49
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What is one thing you do to take care of yourself?

Follow-ups: Why does it work? • How often do you do it?
#50
easy

What is one thing you do that you know is bad for you?

Follow-ups: Why keep doing it? • Will you ever stop?
#51
easy

What is your favorite holiday?

Follow-ups: Why that one? • What is your tradition?
#52
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What is one holiday tradition you could skip?

Follow-ups: Why skip it? • What replaces it?
#53
easy

What is your favorite thing about weekends?

Follow-ups: Why that? • What is your ideal Saturday?
#54
easy

What is one thing you do every single day without fail?

Follow-ups: Why that? • What happens if you skip?
#55
easy

What is your favorite time of year to travel?

Follow-ups: Why then? • Where is the best place?
#56
easy

What is one thing you always pack?

Follow-ups: Why that? • What is it for?
#57
easy

What is one thing you always forget to pack?

Follow-ups: Why that? • What do you do without it?
#58
easy

What is your favorite thing about your city or town?

Follow-ups: Why that? • What would you change?
#59
easy

What is one thing you would change about where you live?

Follow-ups: Why that? • Could it happen?
#60
easy

What is your favorite building or spot nearby?

Follow-ups: Why there? • When do you go?
#61
medium

What is one thing you believe strongly?

Follow-ups: Why that? • Has it been tested?
#62
medium

What is one thing you used to believe strongly?

Follow-ups: What changed? • Do you miss it?
#63
medium

What is a value you will not compromise on?

Follow-ups: Why that value? • Where did it come from?
#64
easy

What is one thing you think the world needs more of?

Follow-ups: Why that? • What do you do about it?
#65
easy

What is one thing you think the world needs less of?

Follow-ups: Why that? • Who is responsible?
#66
easy

What is the best compliment you have ever given someone?

Follow-ups: Why did you say it? • How did they react?
#67
easy

What is one thing you are grateful for today?

Follow-ups: Why today? • Has it been on your mind?
#68
medium

What is one thing that surprised you about adulthood?

Follow-ups: Why the surprise? • Was it good or bad?
#69
easy

What is one thing you miss about childhood?

Follow-ups: Why that? • Could you bring it back?
#70
easy

What is one thing you are excited to get better at?

Follow-ups: Why that skill? • How are you practicing?
#71
easy

What is your proudest non-work accomplishment?

Follow-ups: Why does it matter? • Who celebrated with you?
#72
medium

What is one thing you did that scared you but was worth it?

Follow-ups: Why was it scary? • Would you do it again?
#73
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What is one thing you would do differently if you started over?

Follow-ups: Why that? • What would change?
#74
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What is one thing you are saving up for?

Follow-ups: Why that? • How close are you?
#75
medium

What is one thing money has not been able to buy you?

Follow-ups: Why not? • Is it still possible?
#76
easy

What is your favorite way to meet new people?

Follow-ups: Why that way? • Where do you go?
#77
easy

What is one thing that makes you instantly like someone?

Follow-ups: Why that? • Has it ever failed?
#78
medium

What is one thing that makes you instantly distrust someone?

Follow-ups: Why that? • Has it ever been wrong?
#79
easy

What is the best first impression you have ever made?

Follow-ups: Why did it work? • Did it last?
#80
easy

What is the worst first impression you have ever made?

Follow-ups: What happened? • Did you recover?
#81
easy

What is one thing you do when you are nervous?

Follow-ups: Why that? • Do people notice?
#82
easy

What is one thing you do when you are excited?

Follow-ups: Why that? • Who sees it most?
#83
easy

What is your favorite way to celebrate a birthday?

Follow-ups: Why that way? • What is your best one?
#84
easy

What is one birthday you will never forget?

Follow-ups: Why that one? • What happened?
#85
easy

What is your favorite thing about getting older?

Follow-ups: Why that? • What do you not like?
#86
easy

What is one thing you are less worried about than you used to be?

Follow-ups: Why the change? • What replaced it?
#87
medium

What is one thing you worry about more than you should?

Follow-ups: Why that? • Does it help?
#88
easy

What is your favorite thing to do when you are alone?

Follow-ups: Why alone? • How often do you get to?
#89
easy

What is your favorite thing to do with a big group?

Follow-ups: Why that? • Who is usually there?
#90
easy

What is one thing you do better alone than with others?

Follow-ups: Why alone? • What is the difference?
#91
easy

What is one thing you only do with your closest people?

Follow-ups: Why only them? • When did it start?
#92
easy

What is your favorite thing to talk about late at night?

Follow-ups: Why then? • Who is your late-night person?
#93
medium

What is one thing you think about more than most people?

Follow-ups: Why that? • Does it help?
#94
easy

What is one thing you never think about?

Follow-ups: Why never? • Should you?
#95
easy

What is your favorite thing to daydream about?

Follow-ups: Why that? • Could it happen?
#96
medium

What is one thing you would love to be remembered for?

Follow-ups: Why that? • Are you on track?
#97
easy

What is one thing you want to do before this year ends?

Follow-ups: Why that? • What is step one?
#98
medium

What is one thing you want to do before you die?

Follow-ups: Why that? • What is in the way?
#99
easy

What is one thing you want people to know about you after this conversation?

Follow-ups: Why that? • Did it come across?
#100
easy

What is the best question you have ever been asked?

Follow-ups: Why that one? • What was your answer?
#101
easy

What is one question you hope I ask you next?

Follow-ups: Why that one? • Ask yourself?
#102
medium

What is one thing you learned about yourself recently?

Follow-ups: How did you learn it? • Was it a surprise?
#103
medium

What is one thing you want to learn about yourself?

Follow-ups: Why that? • How would you find out?
#104
easy

What is one thing you think we have in common already?

Follow-ups: Why that? • What else matches?
#105
easy

What is one thing you hope we disagree about so we can debate it?

Follow-ups: Why that topic? • What is your side?