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500 Questions to Ask Anyone

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  • Who do you go out of your way to be nice to?
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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’s wrong but sounds right?
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  • What’s the most creative use of emojis you’ve ever seen?
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  • What makes you roll your eyes every time you hear it?
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  • If you could switch two movie characters, what switch would lead to the most inappropriate movies?
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  • What’s the spiciest thing you’ve ever eaten?
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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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  • When did something start out badly for you but in the end, it was great?
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  • What’s something you really resent paying for?
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  • What mythical creature do you wish actually existed?
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  • What are your most important rules when going on a date?
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  • What was the last photo you took?
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  • What animal would be cutest if scaled down to the size of a cat?
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  • What obstacles would be included in the World’s most amazing obstacle course?
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  • Do you think that aliens exist?
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  • What movie can you watch over and over without ever getting tired of?
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  • What riddles do you know?
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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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  • What is the most amazing slow motion video you’ve seen?
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  • What’s something that will always be in fashion, no matter how much time passes?
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  • What’s the most epic way you’ve seen someone quit or be fired?
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  • What invention doesn’t get a lot of love, but has greatly improved the world?
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  • How do you judge a person?
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  • What’s your cure for hiccups?
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  • What are some red flags to watch out for in daily life?
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  • Which celebrity do you think is the most down to earth?
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  • What would a world populated by clones of you be like?
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  • What “old person” things do you do?
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  • What food is delicious but a pain to eat?
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  • What weird food combinations do you really enjoy?
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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 are you currently worried about?
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  • Where do you get most of the decorations for your home?
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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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  • When was the last time you got to tell someone “I told you so.”?
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  • What’s the most expensive thing you’ve broken?
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  • How would your country change if everyone, regardless of age, could vote?
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  • Where do you get your news?
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  • If someone narrated your life, who would you want to be the narrator?
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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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  • Where are some unusual places you’ve been?
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  • What food have you never eaten but would really like to try?
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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 do you think you are much better at than you actually are?
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  • Who was your craziest / most interesting teacher?
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  • What’s the most interesting building you’ve ever seen or been in?
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  • What social stigma does society need to get over?
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  • Should kidneys be able to be bought and sold?
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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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