Evolutionarily-speaking, we are designed to understand + be understood.
We’ve got five distinct senses.
We’ve got a whole brain region devoted to connecting abstract ideas to words + symbols.
We’ve got 45 miles of nerves running through our bodies, with impulses that travel at 325 miles an hour.
And — depending on your belief system, or how many glasses of Gewurztraminer you’ve imbibed — we’ve got a soul. An essence. A source of intuition.
As human beings, we’re uniquely gifted with the ability to dive deep, to probe + connect, to soften the barricades that divide us, and to really get each other.
We don’t always succeed, of course.
But maybe we’re not asking the right questions …
Here’s a collection of 100 questions to inspire self-discovery + understanding … and maybe your next blog post, journal entry, book outline, first date or dinner party conversation. ❤
Enjoy the Q’s. Go learn something new. Revel in the miracle of your capacity to understand + be understood. (Enough preamble: c’mon, just play!)
ϟ What’s the best compliment you’ve ever received?
ϟ What’s one thing you’re deeply proud of — but would never put on your résumé?
ϟ What’s the most out-of-character choice you’ve ever made?
ϟ If a mysterious benefactor wrote you a check for $5,000 and said, “Help me solve a problem — any problem!” … what would you do with him or her?
ϟ What’s going to be carved on your (hypothetical) tombstone?
ϟ What are you FREAKISHLY good at?
ϟ What’s one dream that you’ve tucked away, for the moment? How come?
ϟ What are you STARVING for?
ϟ If you could have tea with one fictional character, who would it be?
ϟ Do you have a morning ritual?
ϟ Do you believe in magic? When have you felt it?
ϟ Is there something that people consistently ask for your advice on? What is it?
ϟ Have you ever fantasized about changing your first name? To what?
ϟ When was the last time you astonished yourself?
ϟ What’s your personal anthem or theme song?
ϟ Do you ever yearn for your life, before Facebook?
ϟ What’s your definition of an ideal houseguest?
ϟ If you had an extra $100 to spend on yourself every week, what would you do?
ϟ If you could sit down with your 15-year old self, what would you tell him or her?
ϟ What are you BORED of?
ϟ What’s the best birthday cake you ever ate?
ϟ How do you engage with panhandlers on the street?
ϟ Do you think LOVE is chemical, intellectual, spiritual — or completely undefinable?
ϟ Have you ever dreamed about starting a business? (Or if you’ve already got one — a new business?)
ϟ Are you afraid of flying in airplanes? (How come?)
ϟ What’s your most urgent priority for the rest of the year?
ϟ If you could master any instrument on earth, what would it be?
ϟ Have you ever been genuinely afraid for your physical safety?
ϟ What are you an expert on? Is it because of training, lived experience, or both?
ϟ Has a teacher ever changed your life? How so?
ϟ Are there any household chores you secretly enjoy? Which ones — and why?
ϟ How do you reign in self-critical voices?
ϟ If you could custom blend a perfume or cologne, what would it include?
ϟ What does FEAR feel like, in your body?
ϟ Do you think you’re currently operating at 100% capacity?
ϟ What do you value most: free time, recognition, or money?
ϟ If you could save one endangered species from extinction, which would you choose?
ϟ Are there any laws or social rules that completely baffle you?
ϟ Would you like to write a book? (About what?)
ϟ If you could choose your own life obstacles, would you keep the ones you have?
ϟ Have you ever SCREAMED at someone? (What did they do?)
ϟ Do you think there’s going to be an anti-technology whiplash, in our lifetime?
ϟ Where + when do you get your BEST IDEAS?
ϟ Have you ever met one of your HEROES?
ϟ What’s in your fridge, right this moment?
ϟ Can you tell when someone is LYING?
ϟ Can you tell when someone is telling the TRUTH?
ϟ Have you ever pushed your body further than you dreamed possible?
ϟ Are you living your LIFE PURPOSE — or still searching?
ϟ Have you ever had to make a public apology? (How come?)
ϟ What’s the WORST piece of advice you’ve ever been given?
ϟ Do you think we’re designed for monogamy? (Why or why not?)
ϟ How do you CELEBRATE your victories?
ϟ Would you consider yourself an introvert, extrovert, or ambivert?
ϟ Do you ever hunt for answers or omens in dreams?
ϟ Do you think everyone has the capacity to be a LEADER?
ϟ Is WAR a necessary EVIL?
ϟ Are YOU a starter, a finisher, or an implementer?
ϟ Have you ever unplugged from the Internet for more than a week?
ϟ Do you think we should live like we’re dying?
ϟ Do you have any habits or quirks you wish you could ERASE?
ϟ What was the most AGONIZING hour of your life?
ϟ Have you ever dramatically changed a habit, or gotten yourself out of a rut? How’d you do it?
ϟ Would you rather be a lonely genius, or a sociable idiot?
ϟ How would YOU fix the economy?
ϟ What was your very first JOB?
ϟ What brings you SHEER DELIGHT?
ϟ Are you highly useful in a CRISIS?
ϟ Do you like to be SAVED — or do the saving?
ϟ What’s one mistake you keep repeating (and repeating)?
ϟ If you were heading out on a ROAD TRIP right this minute, what would you pack?
ϟ Do you have any irrational fears?
ϟ When you see peers + competitors getting things you want, how do you react?
ϟ If you were to die three hours from now, what would you regret most?
ϟ What’s something you’ve tried, that you’ll never, ever try again?
ϟ If you could enroll in a PhD program, with your tuition paid in full by a mysterious benefactor, what would you study — and why?
ϟ Have you ever had a complete + total nervous breakdown? (How did you recuperate?)
ϟ Have you ever set two friends up on a date? (How did it go?)
ϟ Have you ever questioned your FAITH — or lack thereof?
ϟ What’s your recipe for recuperating from extreme heartbreak?
ϟ Have you ever had a psychic reading? Did you believe it? Was it accurate?
ϟ Have you ever (actually) kept a New Year’s Resolution?
ϟ Have you ever met someone who was genuinely EVIL?
ϟ Do you believe that everyone deserves redemption + forgiveness?
ϟ What was the BEST KISS of your entire life?
ϟ Do you secretly miss Polaroid cameras?
ϟ Do you have any physical features that you try to cloak or hide? How come?
ϟ What makes YOU so special, anyway? (No, really.)
ϟ What’s in your pocket (or purse, or man-purse) right now?
ϟ Ever fantasize about being in a rock band? What would your group be called?
ϟ What’s your guiltiest of guilty pleasures?
ϟ Who’s on your panel of imaginary mentors?
ϟ Have you ever stolen anything? (Money, candy, hearts, time?)
ϟ When was the last time you saw an animal in the wild?
ϟ What’s the hardest thing you ever had to write — and why?
ϟ Who’s the last person that deeply disappointed you? (What happened?)
ϟ Have you ever won an award? What was it for?
ϟ How long can you (comfortably) go without checking your emails or texts? How do you feel about that?
ϟ What do you deserve + get to receive, no matter what?
ϟ What are you ready to set into motion, today?
P.S. Choose your favorite question and answer it, below.
Let the games begin!