Insightful questions

What will always be funny to you?

49. What have you been meaning to do but haven't yet done? Why haven't you done it?

What wouldn't you do for someone you love?

Are there any smells that bring back memories for you? What are they, and what memories do they elicit?

What are you currently worrying about, if anything? What could happen to make you stop worrying about it?

Are you currently pursuing what makes you happy? Why or why not?

What's the best gift you've ever received? Who gave it to you?

Do you have a personal mantra? If so, what is it?

What do you wish was possible?

Do you have any conspiracy theories? If so, what are they?

Have you ever hit "rock bottom"? What did it look and feel like to you? What situations or decisions led to it? How did you get out, or have you gotten out yet?

Have you ever challenged or questioned a belief you held for a long time? What prompted it and what was the result?

What person in your life would you most want to be stuck in an elevator with for 24 hours?

Have you ever desired or longed for something, but once you got it, discovered it was overrated?

What if the first thing you hope people notice about you?

Have you ever gotten the giggles in an inappropriate place? Where was it?

What was the last song that got stuck in your head?

Have you ever had an epiphany? What was it about, and what sparked the realisation?

What is a profession you admire but could never be a part of?

How would you summarise your life so far in one sentence?

What object best defines who you are?

If seasons never changed, which would you most like to live in eternally?

Have you ever gotten a "hunch" about something that turned out to be true?

If you could ask your future self one thing, what would it be?

What is the best compliment you've ever received?

If you could be any mythical creature, what would you be and why?

What is something you had to learn the hard way?

If you could be good at any profession without having to receive the accompanying education or trade experience, which would you choose?

What is the best compliment you've ever given someone?

If you could change one thing about yourself physically, what would you change?

How has your year been going?

If you could erase one thing or event from your memory, what would you choose?

What was the most recent thing that made you belly laugh?

If you could go back and relive one day in your life without changing anything about it, which day would you revisit?

What is something you hate that most people love?

If you could live in another time period but stay in the same place you live now, when would you want to live?

What outfit makes you feel invincible?

If you could play any instrument or learn any language in two hours, which would you choose and how would you use your talent?

What is something that's difficult for you but easy for most other people?

If you could use a time machine, would you rather have one that only goes back in time or only goes forward?

What is something that's easy for you but difficult for most other people?

If you got a promotion, a job, a college acceptance, an accolade/award, or just generally accomplished something major, who is the first person you'd tell and how do you think they'd react?

What is the dumbest purchase you've ever made?

If you had the power to completely eradicate one disease, which would you choose to abolish?

If you had to write your own eulogy to be read at your funeral, what would it say in brief?

If you had the power to completely solve one social or political issue affecting the world today, which would you choose?

How long do you think you could survive in a remote forest with no tools?

If you lived in a colonial or Medieval village, what would your job be?

How are you? No, really. How are you? Not "Fine," not "Good, thanks, and you?" How are you really? Now, today, at this moment?

If you were a character in a movie, book, or television show, what genre would you live in?

What are you glad you learned as a child?

If you were an inanimate object, what would you be and why?

What character trait instantly makes you respect someone?

If you've had more than one job, which job taught you the most?

182. If you could live in any fictional world, where would it be and why?

Imagine that you could choose when and how you die. At what age would you like to die (no maximum here) and how would you like to go?

What's your favourite memory with your best friend?

In what way would you most like to become famous?

If you died today, what would be your biggest regret?

In what ways do you benefit the world?

What about yourself hasn't changed in the last 10 years?

Is there a song/movie/food/etc. that strongly reminds you of someone whenever you experience it? Who does it remind you of?

There is an old, old man who lives deep in the forest. He is immortal, and was born in the year 0. You may ask him one question. What do you ask?

Is there something about you that people assume because of your appearance or demeanour? What is a trait or preference you have that people don't expect you to have?

What gives you hope for the future?

Is there something you wish everybody knew about you without you having to tell them?

What is something that happened to you, despite the odds being stacked against you?

Let's say that regardless of what job you have, you'll make $100,000 a year (£78,000; €90,000), enough to live comfortably without having to worry about expenses. What job would you choose to have if money were no object?

What person you know do you look up to most and why?

Some historical figures have epithets attached to their names, like The Mad or The Wise. What would you like yours to be?

What's the biggest fight you've gotten into, and what was it about?

Think of the best teacher you've ever had. What did they teach, and what made them so special?

What advice do you wish you'd received earlier?

What are the books/movies/games that never get old and always make you feel better when you get down?

What is your favourite question to answer?

What character archetype is closest to your personality?

What's the most selfish thing you've done?

What cliché do you think is bullshit? What cliché do you think holds truth?

How do you think humanity will go extinct? When do you think it will happen?

What did you know was a mistake as soon as you decided to do it, and why did you go through with it anyway?

What's the most selfless thing you've done?

What do you fear, despite having no real reason to do so? Basically, what is an irrational fear you have?

If you were a superhero, what would be your name, costume, and catchphrase? Who would you fight?

What do you get the most compliments about?

Is there something you want to tell someone, but haven't? Why haven't you done it, and how do you think they would react if you told them?

What do you know isn't real, but want badly for it to exist?

What is a misconception people have about your profession?

What do you think "success" means? How do you define it in your own life?

What is a completely rational, justified fear that you have?

What fact about yourself took you the longest to understand or accept?

What will never cease to make you smile?

What fictional character do you most relate to?

If you could change your name (first, last, middle, or any combination of the three), what would you change it to and why?

What has been the biggest change of heart you've had? Have you ever started off on one side of an issue and wound up on the other? What influenced that change?

Assume that god exists. For our purposes, he created the universe and has witnessed everything that has happened since. He also has control over everyone's lives and destinies. Once a millennium, he appears to somebody in his human form and will answer one question with absolute truth. He has chosen you. What do you ask him?

What is a childhood habit or preference that you'll never outgrow?

What about yourself is completely different from what you were like 10 years ago?

What is one childhood memory that you remember especially well?

What was your favourite family tradition growing up? Have you created a tradition of your own?

What is something other people admire about you?

What is the most dangerous thing you've ever done, and why did you do it?

What is something that gets cooler/more interesting the more you learn about it?

What subject could you teach a college course on? What would be the title of the course, and what units would you cover?

What is something you don't realise is weird until you really think about it?

What would the ideal version of your life look like?

What is something you never thought you'd be able to do, until you actually did it?

What is something you want but will never have?

What is something you're terrible at but wish you could do well?

What is the most obscure fact you know?

What is something you've done that you recommend everyone do before they die?

What is a story you always fall back on—one you've told so many times you nearly have it memorised?

What is something you've done/felt/seen/etc. that you wish you could experience again for the first time?

Who was the last person you called, and what did you talk about?

What is the "strangest" thing you believe in? Do you believe in the supernatural? Heaven, angels, ghosts? Luck, fate, magic? Mind reading, lizard people, the Illuminati? Where do you draw the line of belief and disbelief?

221. What is the strongest emotional connection you've ever felt with a person? (It doesn't have to be romantic.)

What is the best advice you've ever received?

If you could enhance one of your senses twofold (e.g. your hearing would be twice as good as it is now), which would you choose to enhance?

What is the closest you've ever come to dying?

What's a rant you've been holding in?

What is the greatest physical pain you've ever felt?

What were you severely underprepared for?

What is the hardest way you've learned an important lesson?

What is the longest or most complex thing you have memorised?

What is the most important quality you look for in a friend? A romantic partner?

What's the best gift you've ever given? Who did you give it to?

What is the most memorable meal you've ever had? (It can be good or bad.) What made it so memorable?

Someone you love will die at the end of today. Only you know this; they don't. How do you spend your last day with them and when do you tell them that they're going to die, if ever?

What is the most ordinary-seeming thing that you find fascinating?

What was the hardest time of your life, and how did you make it through?

What is the most trivial thing about which you have a strong opinion?

What is an "everyday evil" you experience often? Something banal but deeply unfair.

What is the one thing you've made that you're the most proud of?

If you could know for certain the answer to any question, what would that question be?

What is the quality you admire the most in the person you dislike the most?

What stereotype are you most like?

What is the smallest thing for which you are grateful?

Who do you wish was still alive?

What is your biggest academic or work-related accomplishment?

What historical figure would you most like to sit and have a conversation with over tea?

What is your biggest non-academic, non work-related accomplishment?

If you could have any superpower for just one day, but you get to choose the superpower and when you activate it, what would you choose and when would you use it?

What is your favourite word and why?

If you could erase one memory from your mind, what would it be and why?

What is your ideal birthday? Not the date, but rather your ideal way to spend the day.

What is something you love that most people hate?

What is your least popular or most controversial opinion?

What do you wish you remembered better?

What lesson have you had to learn again and again?

What expensive thing is absolutely worth the money?

What one thing, whether it's something you did or something you made or something you caused to happen, would you like to be remembered by?

What do you find yourself thinking about just before you fall asleep?

What question do you most hate being asked?

What is something you know is going to happen, but hasn't yet?

What scientific or technological advance blows your mind? Is there any technology that seems so futuristic and advanced you're surprised it actually exists?

What is a fear you've faced and how did you face it?

What single event or decision do you think most affected the rest of your life? Was there a turning point in your life?

What is something you fantasise about often?

What trait do you admire in others but don't possess yourself?

Has anyone ever saved your life? Have you ever saved someone else's?

What was the best year of your life? The worst?

184. What is the biggest punishment you've ever received? Getting grounded, disciplinary file, prison?

What was the happiest moment of your life so far?

Is there anything you have vowed never to do?

What was the hardest decision you've ever made?

What is a quote that speaks to you, and why do you like it?

What was the most recent thing that made you cry?

You have the opportunity to give a 10 minute speech which will be broadcast worldwide. What do you say?

What was the scariest moment of your life thus far?

210. Who is the single best person you have ever met? What makes them the best?

What was your favourite thing about the place you grew up?

Under what circumstances do you think you could kill someone, if any?

What word would your best friend use to describe you? Your parents? Your significant other (if applicable)?

What do you think is worth dying for, if anything?

What would you title your memoir?

What situation made you feel like a complete idiot?

What's something you wish you enjoyed but never can seem to?

When was the last time you did something nice for someone completely unprompted?

What's the best lesson you've learned from a difficult situation?

What is something you're embarrassed to admit you enjoy? Why are you embarrassed about it?

What's the best outcome of a complete accident you've experienced in your life?

What is the worst thing in your life that has resulted from a complete misunderstanding or miscommunication?

What's the coolest project you've ever worked on?

What one thing changed the way you see the world?

What's the worst advice you've ever been given?

What do you want written on your headstone?

What's your favourite article of clothing you own?

Have you ever had, a recurring dream or nightmare? What was it?

What's your favourite joke you've ever heard?

What current trend do you find troubling and why?

What, if anything, is too serious to be joked about?

If you could know either when you die or how, which would you choose, if either?

Where do you wish you had grown up?

In what way have you experienced the saying, "You don't know what you have until you lose it"?

Which of your flaws are you most proud of?

What is one thing you're proud you haven't done?

Who has had the most positive impact on your life?

Do you have or have you ever had a nemesis?

You have one year to live: how do you spend it?

What is something you enjoyed doing but would never do again?

You're old and on your deathbed. With your last breath, you may deliver your last words to anyone you know. What do you say and who do say it to?