Over 300 Questions to choose from

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What’s your favourite book?

Who is your favourite person right now?

What is your favourite food?

What is your favourite drink?

What is your favourite word?

What is your favourite movie?

What is your favourite song? do you know all the words?

What would you recommend everyone own?

What age would you like to live to?

What is your favourite quote?

What is your favourite day of the year?

What is your favourite smell?

What’s your favourite genre of movie or book?

What fictional place would you most love to visit?

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

What’s the most interesting fact you know?

If you could choose your dreams, what would you prefer to dream about?

Who was your favourite teacher?

What movie, picture, or video always makes you laugh no matter how often you watch it?


If you could invite anyone in the world to dinner, alive or dead, whom would it be?

What small action immediately makes you respect a person?

If you could make any person alive right now cease to exist, whom would it be?

What type of person do you hate the most?

What was the most meaningful interaction you’ve ever had with a stranger?

What kind of people are you attracted to?

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

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

Who is the most gifted person you know?

What is the most annoying habit that other people have?

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

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

Who inspires you to be better?

Who is the scariest person you know?

What was the nicest compliment you’ve received?

What do people think is weird about you?

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

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

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

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

What’s something that a lot of people are missing out on because they don’t know about it?

Who is the most intelligent or creative person you know?

What’s the best or worst prank you’ve played on someone?

Which person that you’ve met had the most interesting name and how did you meet them?


What does friendship mean to you?

What quality do you value most in a friend?

Which friend do you wish you never lost contact with and why? what happened?

Which friend do you have the most in common with?

Who is your closest friend right now?

Which friend makes you a better person?

Who is/was your most interesting friend?

What was the most memorable gift you’ve received?

What would be some of the most annoying things about having yourself as a friend?

What’s the funniest thing you’ve witnessed a friend do?

What has someone borrowed but never given back?

Which friend has the best story behind their nickname?

The Hard Stuff

What is your most terrible memory?

What is one thing you wish you could change about yourself?

What difficult experience did you go through that you wouldn’t change if given the chance?

Have you had a happy life so far?

Have you ever had any physical or mental health issues that deeply affected you?

What do you take for granted?

What is the hardest lesson you’ve learned?

What do you have doubts about?

What fact are you resigned to or believe will never change?

What single event impacted your life the most?

What do you fear and why do you fear it?

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

What are you most scared of?

What are you most insecure about?

What has taken a toll on you?

What is the most physically painful thing you’ve ever experienced?

What job doesn’t exist now but will exist in the future?

What is the most dangerous situation you’ve found yourself in?

Do you believe in god? Describe your faith?


Is there a topic you wished you knew more about?

If you had to change one thing about your past what would it be? Do you regret the path you took?

If you could tell your younger self something what would it be?

What do you wish you started doing earlier?

What advice would you pass onto others from mistakes you’ve made?

When was the last time you broke out of your comfort zone? Do you wish you did it more?

What are some things you’ve had to unlearn?

What bad habit do you wish you never formed?

What risks are worth taking?

What is something you will never do again?

What lesson do you wish you learnt earlier?

What mistake do you keep making again and again?

The Job

What job did you want when you were younger?

What is your current job?

Is your job rewarding?

What’s something you love about your work?

If you could start your career from the beginning again what would you change?

If you could start a new job or project what would it be?

Have you ever lost your job?

What was the worst job you’ve ever had?

Who was the most interesting person you’ve worked with?

Would you rather work until retirement or never work again?

Do you push yourself in your job?

If you had the option to never work a day in your life would you take it?

What was the most interesting to happen while at work?

Do you have anything to say about your work?

What job would you be terrible at?

Do you think you have a pretty good work-life balance? Why or why not?

What’s the hardest you’ve ever worked?

What’s some insider knowledge that only people in your line of work have?


What would your perfect day be like?

If you could wake up to tomorrow with a new superpower, what would it be?

What’s something you’ve dreamed of doing for a long time?

If there was any problem you could fix with the click of your fingers what would it be?

What is your most treasured memory?

What’s the best thing you’ve ever found?

How do you relax after a hard day of work?

What smell reminds you of a different time in your life?

What kind of universe or reality would you most like to live in?

What is the most overrated product or service you know?

If you could be any animal what would it be?

What are you addicted to?

Would you rather spend a night out or a night in?

What company do you despise?

If you lived in a virtual reality world of your creation, what would it look like?

Just You

What’s your most embarrassing moment?

When was the last time you cried about something meaningful?

What’s your secret talent?

If you could be any animal what would it be?

If you had any superpower what would it be?

What was the most exhilarating thing you’ve ever experienced?

What’s one thing you’re sure that nobody else in the world has ever done?

What kind of sports do you enjoy playing? do you still play?

What’s the luckiest thing to have ever happened to you?

What’s one thing you’re pretty sure nobody else does?

What’s something you do alone you’re embarrassed to admit?

If you could make anything at all exist with the click of your fingers what would it be?

Are you an organ donor? Why or why not?

If you could say one thing the whole world would hear what would it be?

How do you start every day?

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

What is the most impressive thing you know how to do? Can you do it now?

If you ruled a small country what kind of laws would you enact?

What’s the most immature thing that you do?

Do you have any tattoos? Any you’d like to show/would you ever like to get one? What’s the story behind it?

What’s the most insignificant thing that you’re proud of?

What do you spend the most time thinking about?

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

What lie do you tell most often?

What’s the most amazing natural occurrence you’ve witnessed?

Things of Importance

If your house was going to burn down and you could only save one object what would it be?

What does success mean to you?

When was the last time you felt truly alive?

Are family or friends more important to you?

What are you determined to do?

What skill would you like to master?

Which goal are you working towards now?

What are some small things that make your day better?

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

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

What topic could you spend hours talking about?

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

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

What do you hope your last words will be?

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

If life is a game like some people say, what are some of the rules?

What’s something people don’t worry about but should?

What’s something important happening right now that people aren’t aware of?

If you were put into solitary confinement for a year, what would you do to stay sane?

If you could have a video of any one event in your life, what event would you choose?

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?

What gives your life meaning?

What’s something that was once important but is now becoming less and less relevant?

What’s the most historically important thing that has happened in your lifetime?

What do you think is an enormous waste of time?

The Past

What happens regularly that would horrify a person from 100 years ago?

What’s quickly becoming obsolete?

How different was the world when you were born to now?

What would you love to ask someone from the past?

What detail about the past shocked you the most?

What about the past are you glad doesn’t exist anymore?

Do you have nostalgia for a period of time?

What from the past would you love to have in the present?

How far back can you trace your family? Do you feel a connection to them?


If you could change one thing about how you were raised what would it be?

Do you feel your childhood was happier than others?

What’s something your family could only understand?

Which death in the family would impact you the most?

Which childhood memory means the most to you?

What’s unique about where you grew up?

What were/are your grandparents like?

Which relative do you wish you knew better?

What do you like most about your family?

Looking back did your parents know what they were doing?

Tell me about your siblings?

What’s the funniest memory you have with your family?

What’s the saddest memory you have with your family?

Which family member do you wish you knew better?

What piece of family history do you hope is never lost?

In what ways are you similar to your parents?

What is something your parents put a lot of emphasis on that turned out to not be important when you grew up?

What’s the most embarrassing story from your childhood?

What did you believe for way too long as a child?


What is too serious to joke about?

What opinion do you have that most people around you don’t share?

How open are you to changing your opinion?

If you could remove any public figure from the spotlight whom would it be?

Would you rather live in the past, present, or future? How far back or into the future?

What do you hope never changes?

What kind of art do you enjoy most?

Do you consider yourself an introvert or extrovert?

What do you think gets too much media attention?

If you could bring back any trend what would it be?

What age do you wish you could permanently be?

What have you only recently formed an opinion about?

What setting do you feel the most comfortable in?

Do you believe in intelligent life outside of Earth?

What is one thing that most people do that you’ll never understand?

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

What subjects should be taught in school but aren’t?

When is the most interesting period in history?

What do you wish was illegal?

What do a lot of people have very strong opinions about, even though they know very little about it?


What’s the farthest you’ve ever been away from home?

What’s the longest time you’ve spent away from home?

Where is the most interesting place you’ve been?

If you could live anywhere else in the world where would it be?

What is your favourite tourist attraction?

Where would you spend all your time if you could?

What would be the most amazing adventure to go on?

What country or place do you never want to go back to?

Where do you usually go when you have time off?

What place do you recommend everyone visit in their lifetime?

In what situation or place would you feel the most out of place?

Would you ever live on another planet if given the opportunity?

What’s the most interesting building you’ve ever seen or been in?

What place from your childhood do you wish you could revisit?


What’s something you lost and were never able to find again?

If you had unlimited funds to build anything at all what would it be?

What’s a responsibility that you have that you’re proud of?

What’s something that happened or something that someone said that changed how you viewed the world?

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

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

Where do you get your news?

Do you believe that there is intelligent life in the universe outside of Earth?

If you could design a flag to represent yourself what would it look like?

What extinct or mythical creature do you wish existed?

If magic was real, what spell would you try to learn first?

If you could know the truth behind any conspiracy which one would it be?

What would the adult version of an ice-cream truck sell?

When was the last time you stayed up through the entire night?

The Future

What do you think the world will look like 100 years from now?

What is something you’re certain won’t exist by the time you pass away?

What is something that will never stop existing far into the future?

What is something you’re certain will exist by the time you pass away?

What kind of future do you hope for this world?

What advice do you have for people in the future?

What goal do you think humanity is not focused enough on achieving?

Do you think that humans will ever be able to live together in harmony?

How do you think civilisation will come to an end?

What’s illegal now, but probably won’t be in 20 years?

What questions would you like to ask someone living 100 years from now?


Did you ever want to be famous?

What’s your greatest accomplishment in life?

What is your claim to fame?

Do you wish you had more than you have now?

How different was your life a few years ago?

How different do you see your life being in a few years?

What one thing do you desire, but can’t afford?

What’s the most valuable thing you own that isn’t monetary in value?

If you could swap places with anyone, whom would it be?

What small change greatly improves a person’s appearance?

Who is the most famous person you’ve met and how did you meet them?

The Exit

Do you have a secret hunch about how you would die?

What are you most grateful for in life?

If you knew that in one year you would die suddenly, would you change anything about the way you’re living now?

What do you want to do when you retire?

What do you want your tombstone to say?

What are you looking forward to in the coming months?

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

What is something you think everyone should experience at least once in their lives?

What is one interesting fact about yourself that we didn’t touch on?

What little piece of information do you never want to be lost?

If you could ask one question to the listener, no matter what year they’re listening, what would it be?

How do you want to be remembered?

Do you have any closing words for the listener?

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