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250 Questions to Get to Know Someone, Not Interview Them

Piercr··19 min read
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250 Questions to Get to Know Someone, Not Interview Them

Key takeaways

  • The best questions to get to know someone are concrete, not clever. Something they can actually answer beats a hypothetical about unlimited money every time.
  • A list of questions becomes an interrogation the moment you work through it in order. The people who get this wrong describe their own conversations as job interviews.
  • In a study of over 2,000 speed dates, asking one extra question per date across twenty dates earned one extra yes. Follow-ups did the work, not openers.
  • Answer your own question before you move on. Disclosure is what turns questioning into conversation.
  • Deep questions land better than you think. Across twelve experiments, people expected them to be awkward and they were not.

In This Post

Why Most Questions to Get to Know Someone Fail

Not because they are bad questions. Because of what happens around them.

Left alone, conversation has a default setting, and the default is narrow. Pew asked more than 5,000 American adults what they discuss with their closest friends. Work came top at 58%, family life at 57%, current events at 48%. That is what people talk about with the people who already know them best. With someone new it collapses further, into work, weather, and where you live.

What people already talk to their closest friends about

So a list helps. The trouble is what people do with a list.

Go and read any forum where people ask how to get better at this and you find the same confession over and over, in almost the same words. One person describes their own method as peppering someone with questions. Another realised, years in, that every conversation they had felt like a job interview. The most upvoted response to that is always some version of the same correction: a question-and-answer format is for interviews and quizzes, and you are not on a fact-finding mission.

That is the failure mode. Not the questions. The sequence.

The second failure is subtler and it is the one every question listicle causes. Abstract questions feel deep and answer badly. Ask someone what they would do with unlimited money and you get a pause, then a shrug, then something they do not mean. Not everyone thinks in extremes, and the ones who do have already answered it. Ask what they spent money on last month that they do not regret and you get a real answer, because it happened.

Concrete beats clever. That rule cuts about a third of the questions on the internet.

The Rule That Stops It Feeling Like an Interview

Answer your own question before you move on.

That is it. It is the difference between an interrogation and a conversation, and it costs nothing. They tell you they moved here for a job they have since left. You say the thing that happened to you, briefly, then ask the follow-up. Now two people are talking.

Drake meme rejecting twenty questions in a row and approving you answer one first

The research backs the follow-up part hard. Harvard researchers coded over 2,000 speed dates and found that asking one extra question per date, across twenty dates, earned one additional yes. The top third of question askers got the most second dates. Of the questions people actually asked, 44% were follow-ups, and those were the ones doing the work.

1 extra yesWhat one additional question per date earned across twenty speed datesHarvard Business School

Alison Wood Brooks, who ran that research at Harvard Business School, is specific about which questions count.

Follow-up questions are an easy and effective way to keep the conversation going and show that the asker has paid attention to what their partner has said.
Alison Wood Brooks, Professor, Harvard Business School · source

Read the list below as ways in, then stay where something interesting happens. One good question you stayed with beats nine you got through.

How to Read the Answers, Not Just Collect Them

Most lists stop at the question. The useful half is what the answer tells you, and it is usually not the content.

What you noticeWhat it usually means
They answer in one line and hand it straight backPoliteness, not disinterest. Go smaller and more specific.
They give you more than you asked forYou hit something they care about. Stay there.
They answer the easy half and skip the restThe skipped half is a boundary. Do not chase it.
They laugh and deflectNot a no. Ask the same thing later, sideways.
They ask it back immediatelyThey want the conversation, not the interview. Answer properly.
Their answer contradicts what they said earlierNot a lie. Two true things. That gap is the interesting part.

Three answers into any of the sections below and you will know which one to keep pulling.

Best Questions to Get to Know Someone

The general-purpose set. These work on a coworker, a date, or someone you met an hour ago.

  1. What did you do last weekend that you would happily do again?
  2. What is something you have changed your mind about in the last year?
  3. What did you want to be when you were ten?
  4. What is the last thing you got properly obsessed with?
  5. Who do you talk to most in a normal week?
  6. What is something you are better at than most people expect?
  7. What is your most-used app that is not social media?
  8. What did you spend money on recently that you do not regret?
  9. What is the best thing that happened to you this month?
  10. What do you do when you have a free Saturday and no plans?
  11. What is something you own that you would replace immediately if you lost it?
  12. Where did you grow up, and did you like it?
  13. What is the last thing you finished, a book or a show or anything?
  14. What is a small thing that instantly improves your day?
  15. What did you think you would be doing by now?
  16. What are you better at than you were a year ago?
  17. What is the most useful thing you learned from a job?
  18. What do people usually get wrong about you at first?
  19. What is something you have never got round to trying?
  20. What is the last photo you took?
  21. What is a strong opinion you hold about something trivial?
  22. What do you do that you would never post about?
  23. What is the longest you have stuck at anything?
  24. Who taught you something that stuck?
  25. What is something happening in your life right now that has nothing to do with work?

What the answers tell you: the give. Some people answer at exactly the length you asked and stop. Some overrun. The overrun is your map.

Fun Questions That Are Not Cringe

Light does not have to mean juvenile. These are the ones that make people laugh and still reveal something.

  1. What is the worst haircut you have ever had?
  2. What food do you defend that everybody else hates?
  3. What is the most useless skill you are weirdly good at?
  4. What is a song you know every word to and are not proud of?
  5. What is the pettiest thing you have ever fallen out with someone about?
  6. What is the dumbest thing you have ever been genuinely scared of?
  7. What is your worst injury and how boring was the cause?
  8. What did you get in trouble for most as a kid?
  9. What is the strangest job you have ever had?
  10. What is your most irrational deal breaker?
  11. What is the worst film you have watched all the way through?
  12. What are you always late for?
  13. What is your go-to karaoke choice, or your reason for refusing?
  14. What is the weirdest thing in your fridge right now?
  15. What was your phase, and how long did it last?
  16. What is the most money you have wasted on something you used twice?
  17. Which conspiracy theory is the funniest to you?
  18. What is a compliment you got that you still think about?
  19. What is the worst haircut, outfit or phase you have photographic evidence of?
  20. What is your most controversial food combination?
  21. What would your sport be if you had to compete in the Olympics tomorrow?
  22. What is the last thing that made you laugh out loud on your own?
  23. What is your useless superpower?
  24. What is the most embarrassing thing in your search history that you would still admit to?
  25. What is something everyone loves that you find exhausting?

What the answers tell you: whether they can be unimpressive on purpose. People who can laugh at themselves early are usually easier to know later.

Deep Questions to Get to Know Someone

The ones people avoid because they assume they will be awkward. The research says otherwise, and there is a whole section below on why.

12 experimentsFound deep conversations between strangers were less awkward than the people having them predictedJournal of Personality and Social Psychology
  1. What is something you are still working out?
  2. When did you last change your mind about something that mattered?
  3. What do you worry about that you never say out loud?
  4. What did your family teach you that you have kept?
  5. What did your family teach you that you have dropped?
  6. What are you most proud of that nobody would guess?
  7. Who do you miss?
  8. What is the hardest thing you have done that you would do again?
  9. What do you want that you feel silly wanting?
  10. What is something you used to believe about yourself that turned out not to be true?
  11. When do you feel most like yourself?
  12. What decision are you still not sure about?
  13. What do you do when things get hard, honestly?
  14. What is a compliment you cannot accept?
  15. What are you avoiding right now?
  16. What would you tell yourself at nineteen?
  17. What is something you have forgiven someone for?
  18. What is something you have not?
  19. Who knows you best, and what do they know that others do not?
  20. What is a version of your life you think about that never happened?
  21. What do you need more of at the moment?
  22. When did you last feel genuinely proud of yourself?
  23. What do you spend the most time thinking about?
  24. What has been the best year of your life so far?
  25. What would have to be true for you to say your life is going well?

What the answers tell you: how much they trust you already, which is usually more than you assume. Ask one of these, then answer it yourself, then stop talking.

Questions for a New Friend

Friendship needs a different set. You are not assessing compatibility, you are finding overlap.

  1. What do you do that you wish more people wanted to do with you?
  2. Are you a plan-it-weeks-ahead person or a text-me-at-six person?
  3. What do you never say no to?
  4. What is a thing you have been meaning to go to and never do alone?
  5. How do you feel about phone calls?
  6. What is your Sunday usually like?
  7. Are you better in a group or one to one?
  8. What is something you would happily be dragged along to?
  9. What do you cook when you cannot be bothered?
  10. Which of your friendships has lasted longest and why?
  11. What is a hobby you are bad at and keep doing anyway?
  12. What do you do when you have not seen anyone in a week?
  13. What is your friend group like?
  14. How far will you travel for good food?
  15. What do you need from a friend when things go wrong?
  16. Are you a texter or a voice-note person?
  17. What is the last new thing you tried?
  18. Do you like being invited to things you will probably decline?
  19. What is something you know a lot about that never comes up?
  20. What kind of plans do you always regret saying yes to?
  21. What do you do on your birthday?
  22. Who introduced you to something you still love?
  23. What would you want more of if time and money were not the problem?
  24. How do you feel about being asked for help?
  25. What would make you say yes to something on a Tuesday?

What the answers tell you: logistics, mostly. Most friendships die of scheduling, not of incompatibility. The two questions about plans are the most useful ones here.

Questions for a First Date

Concrete, easy to answer, and none of them are an interview about their five year plan. If you want the longer version we broke this down in questions to ask on a first date.

  1. What made you say yes to this?
  2. What did you do today before this?
  3. What is your week normally like?
  4. What is something you are looking forward to?
  5. What do you do that you would still do if it paid nothing?
  6. What is the best thing you have eaten recently?
  7. Where do you go when you want to be somewhere else?
  8. What did you think you would end up doing?
  9. What is the last thing you booked?
  10. What are you into that you cannot explain to people quickly?
  11. What is your relationship with your phone like?
  12. What do your friends come to you for?
  13. What is something you have got noticeably better at?
  14. What was the last thing that annoyed you?
  15. What did you do the last time you had a whole day free?
  16. How do you know your closest friend?
  17. What is something you would do more of if you were braver?
  18. What is the most spontaneous thing you have done that worked out?
  19. What is your idea of a good Sunday?
  20. What are you reading, watching or listening to right now?
  21. What do you miss about being younger?
  22. Where have you been that you would go back to tomorrow?
  23. What is something small that you are very particular about?
  24. What is the nicest thing anyone has done for you recently?
  25. What would you want to do next time?

What the answers tell you: number 125 is the only one that matters for the outcome, and it is not a trick. Ask it and you will know. For what to do with the rest of the evening, what to talk about on a first date covers the middle stretch where most dates go quiet.

Questions to Ask Your Crush

Someone you like and do not know yet. The job is not to impress, it is to find out whether there is anything there.

  1. What is something you are into that I would never guess?
  2. What is the best thing that has happened to you this week?
  3. What do you do when you are procrastinating?
  4. What did you nearly do instead of what you are doing now?
  5. What is something you have wanted to try for ages?
  6. What is your most-played song at the moment?
  7. What is the last thing that genuinely surprised you?
  8. What do you do that puts you in a good mood every time?
  9. What are you funny about?
  10. What is the thing you would talk about all night if someone let you?
  11. What is your worst habit that you are not sorry about?
  12. What did you like doing at fifteen that you still like now?
  13. What kind of tired are you at the end of a good day?
  14. What would you do with a free afternoon and no phone?
  15. What is something you are secretly competitive about?
  16. What is your comfort watch?
  17. What is the last risk you took?
  18. What makes you lose track of time?
  19. What is a place you want to go for a reason that is not the obvious one?
  20. What do you notice about people first?
  21. What is something you would want someone to know early?
  22. What are you like when you are stressed?
  23. What is the nicest thing about your week?
  24. What do you want more of right now?
  25. What should I ask you that I have not?

What the answers tell you: effort. Someone interested gives you more than the question asked for, then asks something back. Someone being polite does neither. There is a fuller read on this in how to tell what a girl is into.

Generic versus specific, same person

Genericso what are your hobbies?
Specificwhat is the thing you would talk about all night if someone let you?

the first asks for a list, the second asks for enthusiasm

Generichow was your weekend?
Specificwhat did you do on Saturday that you would do again?

specific enough that fine is not an answer

Generictell me about yourself
Specificwhat is something you are into that I would never guess?

gives them a way in instead of a blank page

Questions for Work and Coworkers

Same principle, tighter boundaries. These get past name and job title without getting personal.

  1. What did you do before this?
  2. What part of your job would you keep if you could only keep one?
  3. What is the thing people always ask you for help with?
  4. How did you end up in this field?
  5. What is the most useful thing you have learned here?
  6. What do you work on that nobody sees?
  7. What would you be doing if you had gone the other way at some point?
  8. What is your most productive time of day?
  9. What is a tool or system you would not give up?
  10. What was your first job?
  11. What is the best manager you have had actually like?
  12. What is something you learned the hard way?
  13. What do you wish you had known starting out?
  14. What is the strangest thing that has happened to you at work?
  15. What does a good week look like for you?
  16. What do you do to switch off?
  17. What are you working on that you are actually interested in?
  18. What is something in this industry that everyone believes and you do not?
  19. How do you prefer to get feedback?
  20. What is the last thing you learned that was not work related?
  21. What is the project you are proudest of?
  22. What is your commute like, and what do you do during it?
  23. What do you do when you are stuck?
  24. What would you change about how we work if it were up to you?
  25. What is something you are trying to get better at?

What the answers tell you: number 168 separates people who think about their job from people who do it. Both are fine. Only one is interesting to talk to.

Questions That Work Over Text

Text kills long questions. These are short, easy to answer with one thumb, and hard to answer with one word.

  1. What is happening in your day?
  2. What is the last photo on your phone?
  3. What are you avoiding right now?
  4. Best thing you have eaten this week?
  5. What is playing?
  6. Where are you and what can you see?
  7. What made you laugh today?
  8. What is the plan for the weekend?
  9. What are you watching at the moment?
  10. What is the most annoying thing about today?
  11. What did you have for lunch and was it a mistake?
  12. What is on your list that you keep moving?
  13. What is the last thing you bought?
  14. Are you a morning person, honestly?
  15. What is one thing you want to do this month?
  16. What is your Friday looking like?
  17. What is something you are looking forward to?
  18. What are you doing that you should not be doing right now?
  19. What is the weather doing where you are?
  20. What is the best thing that has happened this week?
  21. What should I be watching?
  22. What is your controversial opinion about this place?
  23. What is the last thing that made you say no way out loud?
  24. What is your current obsession?
  25. What are you doing later?

What the answers tell you: speed and length. If the reply is shorter than yours twice in a row, ask fewer questions and say more things. How to never run out of things to say is the fix for the stretch after this one.

Two buttons meme: ask something specific, or ask how was your weekend

Questions That Get Past Small Talk

For when you have done the openers and the conversation is idling. Every one of these has a bigger question hiding behind it.

  1. What have you been thinking about lately?
  2. What is something you have changed your mind about?
  3. What do you do that you would be embarrassed to admit you enjoy?
  4. What is the most useful bad advice you have received?
  5. What is something you believe that most people around you do not?
  6. What is a rule you live by that you never explain?
  7. What are you tired of talking about?
  8. What is the last thing that genuinely moved you?
  9. What is a normal thing you find strange?
  10. What is something you would do differently if nobody would know?
  11. What has been on your mind that has nothing to do with anything?
  12. What is a decision that turned out better than it should have?
  13. What is a thing you are not good at and have made peace with?
  14. What has surprised you about getting older?
  15. What is something you thought would matter more than it does?
  16. What is a habit that changed something for you?
  17. What do you notice that other people miss?
  18. What have you failed at recently?
  19. What do you defend that you know is indefensible?
  20. What is the last thing that made you reconsider something?
  21. What is a good problem you have?
  22. What do you think you are wrong about?
  23. What is the most interesting thing you have read this year?
  24. What is something you want to be true?
  25. What question do you wish people asked you?

What the answers tell you: number 225 is the shortcut. People will tell you exactly what they want to be asked, and almost nobody ever asks. If you have found common ground already, how to find common ground with a girl has the follow-through.

Rapid Fire and This or That

For groups, for lulls, for when someone is too tired for a real question. Two words each, and every one has a follow-up in it.

  1. Coffee or tea?
  2. Early or late?
  3. Mountains or sea?
  4. Text or call?
  5. Cook or takeaway?
  6. Window or aisle?
  7. Books or films?
  8. Cats or dogs?
  9. Sweet or savoury?
  10. Big night or big morning?
  11. Plan or wing it?
  12. Cinema or sofa?
  13. Bath or shower?
  14. Summer or winter?
  15. Front row or back row?
  16. Same holiday twice or somewhere new?
  17. City or countryside?
  18. Loud bar or quiet pub?
  19. Surprise party or absolutely not?
  20. Sunrise or sunset?
  21. One best friend or a big group?
  22. Drive or be driven?
  23. Save it or spend it?
  24. Salt or pepper?
  25. Answer honestly or answer well?

What the answers tell you: nothing on their own. The follow-up is the whole point. Every one of these is an excuse to ask why, and the why is where the actual answer lives.

What the Research Says

The most useful finding here is that the thing everyone avoids is the thing that works.

Researchers at Chicago Booth, Northwestern and UT Austin ran twelve experiments with more than 1,800 people, pairing strangers and giving some of them shallow questions and others deep ones. The deep conversations were less awkward, more enjoyable and more connecting than the participants themselves had predicted. People were especially wrong about deep questions specifically. They braced for something that did not happen.

Hard to swallow pills meme: they wanted deep conversation too
Americans have far fewer people who know them well

That matters more than it used to. The share of Americans who say they have no close friends went from 3% in 1990 to 12% in 2021, and those reporting ten or more fell from 33% to 13%. For men the drop is steeper: 3% to 15% with no close friends, and 40% to 15% with ten or more. In the same survey only 30% of men had shared a personal feeling with a friend that week, against 48% of women, and the share of people who turn to a friend first with a personal problem fell from 26% to 16%.

Nicholas Epley, who co-authored the deep conversation research at Chicago Booth, put the cost plainly.

Strengthening social relationships is critical for wellbeing, meaning that a reluctance to engage more deeply with others may leave people being less social than would be optimal for their own wellbeing.
Nicholas Epley, Professor of Behavioral Science, University of Chicago Booth School of Business · source

None of which requires you to be interesting. Larry King spent five decades asking people questions on radio and television, and put his whole method in one line in his book Truth Be Told.

I remind myself every morning: Nothing I say this day will teach me anything. So if I am going to learn, I must do it by listening.
Larry King, Broadcaster, five decades of interviews · source

If you would rather know something real about someone before you open with any of this, put their Instagram username into Piercr and read what comes back first. It is easier to ask a good question when you already know what they care about.

Questions to Skip, and What to Do If One Lands Badly

Some of these will be wrong for the person in front of you. That is normal and it is recoverable.

The ones that reliably misfire

Anything phrased as unlimited: unlimited money, unlimited time, a superpower. They sound deep and answer flat. Anything about exes on a first meeting. Anything about salary, weight, or why someone does not have children. And any question you would not answer yourself, which is the fastest test there is. If a question lands badly, do not apologise twice and do not explain why you asked. Answer it yourself, briefly, and move on. The apology is what makes it a moment.

Brooks is blunt about the other risk, which is asking well and disclosing nothing.

Asking a barrage of questions without disclosing information about yourself may come across as guarded, or worse, invasive.
Alison Wood Brooks, Professor, Harvard Business School · source

Watch for the answer that stops short. Someone who answers the easy half of a question and skips the rest has told you where the line is. Take the answer you were given.

Your Move

None of this works if you open the page and read from number one. Six things, and the first two are the whole game.

How to actually use 250 questions

  • Pick three from one section before you go in. Not thirty.
  • Ask one, then answer it yourself before you ask anything else.
  • When an answer runs long, stop and follow it. That is the conversation starting.
  • Swap any question about unlimited anything for one about last month.
  • If they answer half, leave the other half alone.
  • End on 125 or 225: what would you want to do next time, and what do you wish people asked you.

Two hundred and fifty questions is not a script. It is a way of never being stuck, which is a different and more useful thing. The best conversation you have this month will come from one of these and then twenty minutes that had nothing to do with the list.

Before you ask any of it, it helps to know what the person actually cares about. Piercr reads a public Instagram profile and tells you what they are into, so your first question can be about something real instead of the weather.

Frequently Asked Questions

What are the best questions to get to know someone?

Concrete ones. Something that happened, rather than something hypothetical. What did you do last weekend that you would do again beats what would you do with unlimited money, because the first has an answer and the second has a performance. Start at number 1 above and stay wherever the answer runs long.

How many questions should I actually ask?

Fewer than you think, and follow up on all of them. The Harvard speed dating data found the gain came from one additional question per date, not from a barrage, and 44% of the questions people asked were follow-ups rather than new topics. Three questions you stayed with beat fifteen you moved through.

How do I get the other person to ask me questions back?

Answer your own question before you move on. Most people who complain that conversations feel one sided are asking and never disclosing, which reads as an interview and gives the other person nothing to grab. Say your version, keep it short, then hand it back.

Are deep questions too much for someone I just met?

Less than you expect. In twelve experiments with over 1,800 participants, people consistently overestimated how awkward a deep conversation with a stranger would be, and the deep conversations produced more connection than the shallow ones. Read the room, but assume you are being more cautious than you need to be.

What questions should I never ask?

Exes on a first meeting, money, bodies, and why someone does not have children. Beyond that, the working test is whether you would answer it yourself right now. If you would hesitate, do not ask it yet.

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