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500 Questions to Ask Anyone
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What big event do you think will happen soon that most people aren’t expecting?
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What did you believe for way too long as a child?
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What two things are terrible when separate but great when you put them together?
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What escalated very quickly?
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If you lived in a virtual reality world of your own creation, what would it look like?
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If you could teleport anything you want, worth two million dollars or less, anywhere you want, what would you choose and where would you teleport it?
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If you were a clown themed super hero, what powers would you have?
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What was the most important appointment or deadline you missed?
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What story you’ve heard has stayed with you and always disturbs you every time you think about it?
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What was the worst shopping experience you’ve ever had?
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What would the box with all your hopes and dreams inside look like?
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What fictional characters have you had a crush on over the years?
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What animal would you most like to eat?
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Do you like things to be carefully planned or do you prefer to just go with the flow?
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What’s fine in small numbers but terrifying in large numbers?
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Who did you use to look up to, but they screwed up and you lost faith in them?
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What’s the creepiest tech out there?
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What’s the most boring sport, and what would you do to make it more exciting?
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If you could talk to animals and they would understand you, but you couldn’t understand them, what would you do with that power?
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What sport could you play the longest in a televised game, without anyone discovering you aren’t a professional athlete?
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What always cheers you up when you think about it?
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What’s the weirdest text or email you’ve gotten?
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What’s something that everyone knows is true, but we don’t like to admit it?
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What animal is the most majestic?
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What’s the most embarrassing story from your childhood?
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What’s the funniest TV show you’ve ever seen?
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What’s the weirdest thing you’ve found lying on the ground / side of the road?
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What naps are the most satisfying?
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What word do you always misspell?
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What’s the most overrated product out on the market?
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What is the best compliment a woman has ever given you?
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What is the most important lesson you'll teach your children?
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If something terrible happened to you, who would be the first person you'd call?
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What content do you watch the most?
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Would you rather be extremely smart or extremely happy?
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If you could travel through time only once, would you go to the past or the future?
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What is the biggest animal you could defeat with no weapons?
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If you had to give a speech with no time to prepare, what would you talk about?
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If you were a woman, what type of man would you date?
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How do you know you really like someone?
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What is the most important text message you've ever received?
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What would be an accurate tag line for each month?
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When was the most inappropriate time you busted out in laughter?
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What company do you despise?
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What would the adult version of an ice-cream truck sell and what song would it play?
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What’s your grossest bug story?
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What’s incredibly cheap and you would pay way more for?
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What trend are you tired of?
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What’s something that everyone agrees we should change, but somehow it never changes?
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What’s the most anxiety inducing thing you do on a regular basis?
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What’s the most beautiful beach you’ve been to?
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Tear gas makes people cry and laughing gas makes people giggle, what other kinds of gases do you wish existed?
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What’s the best way you or someone you know has gotten out of a ticket / trouble with the law?
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What’s your secret talent?
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What’s the funniest thing you’ve seen a kid do?
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If you had a HUD that showed three stats about any person you looked at, what three stats would you want it to show?
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Which apocalyptic dystopia do you think is most likely?
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What’s your best story of you or someone else trying to be sneaky and failing miserably?
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What fashion trend makes you cringe or laugh every time you see it?
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Who in your life has the best / worst luck?
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What food do you crave most often?
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What’s the best lesson you’ve learned from a work of fiction?
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What’s the coolest animal you’ve seen in the wild?
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What qualities do all your friends have in common?
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What inconsequential super power would you like to have?
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What’s the most frustrating product you own?
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What’s the saddest scene in a movie or TV series?
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What’s the longest rabbit hole you’ve been down?
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If money and practicality weren’t a problem, what would be the most interesting way to get around town?
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What’s the dumbest thing someone has argued with you about?
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What did you Google last?
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What’s your haunted house story?
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What’s the most annoying noise?
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What’s the smartest thing you’ve seen an animal do?
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What are some misconceptions about your hobby?
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What’s a common experience for many people that you’ve never experienced?
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What’s the worst movie trope?
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What’s the most recent show you’ve binge watched?
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What do you think could be done to improve the media?
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Where are you not welcome anymore?
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What was one of the most interesting concerts you’ve been to?
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What movie or book do you know the most quotes from?
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If you had to disappear and start a whole new life, what would you want your new life to look like?
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What’s the most awkward thing that happens to you on a regular basis?
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What brand are you most loyal to?
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What’s the grossest food that you just can’t get enough of?
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What’s the most amazing true story you’ve heard?
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What’s the scariest non-horror movie?
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What would your perfect bar look like?
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Do you think that humans will ever be able to live together in harmony?
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What scientific discovery would change the course of humanity overnight if it was discovered?
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If you built a themed hotel, what would the theme be and what would the rooms look like?
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What would be the click-bait titles of some popular movies?
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What’s your funniest story involving a car?
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When was a time you acted nonchalant but were going crazy inside?
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What has been blown way out of proportion?
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What happens in your country regularly that people in most countries would find strange or bizarre?
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What’s the most historic thing that has happened in your lifetime?
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What’s the worst thing you’ve eaten out of politeness?
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What’s the most ridiculous animal on the planet?
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Who do you feel like you know even though you’ve never met them?
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f you could hack into any one computer, which computer would you choose?
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What movie universe would be the worst to live out your life in?
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What life skills are rarely taught but extremely useful?
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What kinds of things do you like to cook or are good at cooking?
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What’s the opposite of a koala?
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When was the last time you yelled at someone?
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What about humans confuses you the most?
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If you were given one thousand acres of land that you didn’t need to pay taxes on but couldn’t sell, what would you do with it?
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What habit do you have now that you wish you started much earlier?
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What’s the worst hairstyle you’ve ever had?
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What animal would be the most terrifying if it could speak?
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If you could know the truth behind every conspiracy, but you would instantly die if you hinted that you knew the truth, would you want to know?
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What’s your “Back in my day, we…”?
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What’s the craziest video you’ve ever seen?
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If there was a book of commandments for the modern world, what would some of the rules be?
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What are some of the best vacations you’ve had?
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If people receive a purple heart for bravery, what would other color hearts represent?
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How do you make yourself sleep when you can’t seem to get to sleep?
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Who do you wish you could get back into contact with?
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What’s some insider knowledge that only people in your line of work have?
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What’s the funniest word in the English language?
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What country is the strangest from your cultural stand point?
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What’s something that everyone, absolutely everyone, in the entire world can agree on?
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What’s the most pleasant sounding accent?
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What languages do you wish you could speak?
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What’s your best story from a wedding?
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What’s something that all your friends agree on?
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Where’s your go to restaurant for amazing food?
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What actors or actresses can’t play a different character because they played their most famous character too well?
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What current trend do you hope will go on for a long time?
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What word is a lot of fun to say?
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What would be some of the downsides of certain superpowers?
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What’s the most boring super hero you can come up with?
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When is censorship warranted?
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As a child, what did you think would be awesome about being an adult, but isn’t as awesome as you thought it would be?
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What was the best thing that happened to you today?
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What animal or plant do you think should be renamed?
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What’s the silliest thing you’ve seen someone get upset about?
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What bit of trivia do you know that is very interesting but also very useless?
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What did you think was going to be amazing but turned out to be horrible?
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What would be the best thing you could reasonably expect to find in a cave?
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When was the last time you immediately regretted something you said?
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What was your most recent lie?
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Who has zero filter between their brain and mouth?
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What’s your worst example of procrastination?
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How comfortable are you speaking in front of large groups of people?
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When was the last time you slept more than nine hours?
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What really needs to be modernized?
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Which of your vices or bad habits would be the hardest to give up?
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If you were given five million dollars to open a small museum, what kind of museum would you create?
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What’s the funniest thing you’ve done or had happen while your mind was wandering?
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What was the last song you sang along to?
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What’s the most interesting documentary you’ve ever watched?
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What songs hit you with a wave of nostalgia every time you hear them?
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What outdoor activity haven’t you tried, but would like to?
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What tips or tricks have you picked up from your job / jobs?
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What’s the most depressing meal you’ve eaten?
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What’s the funniest comedy skit you’ve seen?
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What’s the most ridiculous thing you have bought?
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Do you eat food that’s past its expiration date if it still smells and looks fine?
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Which protagonist from a book or movie would make the worst roommate?
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Where's the coldest you’ve ever been?
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What’s the most addicting game?
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If animals could talk, which animal would be the most annoying?
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If you could have an all-expenses paid trip to see any famous world monument, which monument would you choose?
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What artist or band do you always recommend when someone asks for a music recommendation?
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What movie, picture, or video always makes you laugh no matter how often you watch it?
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What’s the hardest you’ve ever worked?
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What’s the craziest conversation you’ve overheard?
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What’s the most comfortable bed or chair you’ve ever been in?
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What game have you spent the most hours playing?
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What character in a movie could have been great, but the actor they cast didn’t fit the role?
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What goal do you think humanity is not focused enough on achieving?
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If you were a ghost and could possess people, what would you make them do?
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If magic was real, what spell would you try to learn first?
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What’s the most ironic thing you’ve seen happen?
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If you were moving to another country, but could only pack one carry-on sized bag, what would you pack?
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What was cool when you were young but isn’t cool now?
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What TV show character would it be the most fun to change places with for a week?
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Which charity or charitable cause is most deserving of money?
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What’s the funniest actual name you’ve heard of someone having?
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What’s the funniest joke you know by heart?
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Do you think that children born today will have better or worse lives than their parents?
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What movie quotes do you use on a regular basis?
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What’s something people don’t worry about but really should?
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What smartphone feature would you actually be excited for a company to implement?
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If you were given a PhD degree, but had no more knowledge of the subject of the degree besides what you have now, what degree would you want to be given to you?
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What are you interested in that most people aren’t?
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Which celebrity or band has the worst fan base?
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When was the last time you were snooping, and found something you wish you hadn’t?
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What unethical experiment would have the biggest positive impact on society as a whole?
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What was the most unsettling film you’ve seen?
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If someone narrated your life, who would you want to be the narrator?
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How do you judge a person?
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What are your most important rules when going on a date?
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What mythical creature do you wish actually existed?
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What’s the most interesting building you’ve ever seen or been in?
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What invention doesn’t get a lot of love, but has greatly improved the world?
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What’s your cure for hiccups?
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What riddles do you know?
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When was the last time you got to tell someone “I told you so.”?
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What’s the most creative use of emojis you’ve ever seen?
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Should kidneys be able to be bought and sold?
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What do you think you are much better at than you actually are?
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What makes you roll your eyes every time you hear it?
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What obstacles would be included in the World’s most amazing obstacle course?
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What’s the most expensive thing you’ve broken?
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What’s the spiciest thing you’ve ever eaten?
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What would be the worst thing to hear as you are going under anesthesia before heart surgery?
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Which celebrity do you think is the most down to earth?
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What is the most amazing slow motion video you’ve seen?
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What was the last photo you took?
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What “old person” things do you do?
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Who was your craziest / most interesting teacher?
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What food is delicious but a pain to eat?
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Where do you get most of the decorations for your home?
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Who do you go out of your way to be nice to?
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What’s the best / worst practical joke that you’ve played on someone or that was played on you?
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In the past people were buried with the items they would need in the afterlife, what would you want buried with you so you could use it in the afterlife?
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What actors or actresses play the same character in almost every movie or show they do?
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What’s something that will always be in fashion, no matter how much time passes?
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If you couldn’t be convicted of any one type of crime, what criminal charge would you like to be immune to?
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What’s the most epic way you’ve seen someone quit or be fired?
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What’s wrong but sounds right?
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If your job gave you a surprise three day paid break to rest and recuperate, what would you do with those three days?
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What animal would be cutest if scaled down to the size of a cat?
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How would your country change if everyone, regardless of age, could vote?
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When did something start out badly for you but in the end, it was great?
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What inanimate object would be the most annoying if it played loud upbeat music while being used?
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If you could switch two movie characters, what switch would lead to the most inappropriate movies?
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When you are old, what do you think children will ask you to tell stories about?
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What movie can you watch over and over without ever getting tired of?
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What are some red flags to watch out for in daily life?
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Where do you get your news?
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Where are some unusual places you’ve been?
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What are you currently worried about?
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Do you think that aliens exist?
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What would a world populated by clones of you be like?
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What’s something you really resent paying for?
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What food have you never eaten but would really like to try?
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What social stigma does society need to get over?
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What weird food combinations do you really enjoy?
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