171 Deep Would You Rather Questions to Know Someone Better

Home » Quotes & Affirmations » 171 Deep Would You Rather Questions to Know Someone Better
Grab Your Free Report: 39 Online Business Ideas for Introverts

There might be affiliate links on this page, which means we get a small commission of anything you buy. As an Amazon Associate we earn from qualifying purchases. Please do your own research before making any online purchase.

If you are meeting someone for the first time, you might be wondering how you can get to know them better. While there are generic questions you can ask them, you might be looking for ways to get to know that person on a deeper level.

That’s why in this post, I will share a list of “would you rather” questions that you can use to get to know someone on a deeper, more personal level. This should strengthen the connection you have with that person.

What Are Would You Rather Questions?

A “would you rather” question is set up to force the recipient to choose between two (or more) options. In this manner, you can target a specific part of someone’s thinking to see how they process information, what they like in life, and get to know them better. Often, the recipient will respond with some questions for you! This is a fun way to get to know the person better, break the ice, and inject a bit of humor into the conversation.

If you feel awkward around someone you don’t know, try to relax! This is normal! The whole idea of “would you rather” questions is to take this feeling of awkwardness and channel it in a productive way. Would you rather questions are unique because they represent a deviation from the way most people ask questions when they are getting to know someone better. That is the joy in these questions.

With this in mind, there is a list of 171 would you rather questions that you can use to get to know someone better. While you might not have to use all of them, you can look through the list and find the ones that you like the best! Then, the next time you are trying to get to know someone better, you can put these questions to you!

171 Would You Rather Questions

  1. Would you rather find your true love in life or land your dream job?
  2. Would you rather like to know when your life is going to end or how you are going to die?
  3. Would you rather like to live in a world that didn’t have music or a world that didn’t have television?
  4. Would you rather have the power to travel back in time or forward in time?
  5. Would you rather want to have the ability to walk on water or bend time and space?
  6. Would you rather live the rest of your days dealing with silent gas that you couldn’t control or loud sneezing that you couldn’t stop?
  7. Would you rather have all of your shirts be two sizes too big or a single size too small?
  8. Would you rather be forced to speak in a way that only involves rhyming or speak in a way that uses constant alliteration?
  9. Would you rather be trapped in a room with 1 million tarantulas for ten minutes or be forced to eat ten tarantulas in ten minutes?
  10. Would you rather be forced to never wear makeup again in your life or be forced to never leave the house again without a complete face full of makeup from a children’s set?
  11. Would you rather have the power to make two people fall in love with each other or have the power to read people’s minds?
  12. Would you rather be forced to forget who you are every time it rains or never be able to remember why you walked into a store, office, or room?
  13. Would you rather be forced to dress in lime green every day for the rest of your life or hot pink every day for the rest of your life?
  14. Would you rather be forced to work for a boss you hate but be paid as much as you want or be forced to work for a boss you love for minimum wage?
  15. Would you rather get your paycheck doled out in pennies every day or never have the ability to buy something with cash ever again?
Would You Rather Questions - Would you rather get your paycheck doled out in pennies every day or never have the ability to buy something with cash ever again? | deep would you rather questions | would you rather questions for couples | emotional would you rather questions #affirmations #wouldyourather #question
  1. Would you rather lose the ability to sing completely or be forced to break out into an uncontrollable dance every time someone so much as hums?
  2. Would you rather marry the smartest person on the planet or marry the hottest person you have ever seen?
  3. Would you rather be forced to wear sweatpants every day for the rest of your life or never be allowed to wear sweatpants ever again?
  4. Would you rather have an itch that you physically cannot reach or have a song that is stuck in your head that you cannot get out?
  5. Would you rather be stranded in a jungle surrounded by animals and poisonous plants or be stranded in a desert without any water or sense of direction?
  6. Would you rather be forced to keep the same job for the rest of your life or have to change jobs regularly every year or two?
  7. Would you rather have every movie spoiled for you before you have had a chance to see it or be forced to wait at least a year to watch a new movie every time it comes out?
  8. Would you rather know everything about the deepest parts of the ocean or know everything about the outer reaches of space?
  9. Would you rather share your house with a family of rodents or be forced to live every day with your parents for the rest of your life?
  10. Would you rather be forced to wash your hair every day with dish detergent or be forced to wash all of your dishes using shampoo and conditioner?
  11. Would you rather be forced to watch all of your top shows live and sit through every ad break or DVR every episode but never know the ending of any episode before the recording always cut off a few minutes too soon?
  12. Would you rather always be able to know what time it is or always have the exact change that you need to make a purchase?
  13. Would you rather be a villain who is known by everyone or be a superhero that nobody knows?
  14. Would you rather be forced to eat a side of cat food with every meal or a side of dog treats with every dish?
  15. Would you rather be a transcendent painter who moves hearts or a famous scientist who discovers secrets?
Would You Rather Questions - Would you rather be a transcendent painter who moves hearts or a famous scientist who discovers secrets? | would you rather questions for guys | would you rather questions for kids | mind blowing would you rather questions #affirmationstoself #questionstoself #mantra
  1. Would you rather be forced to always walk with rocks in your shoes or always walk with mud in your shoes and socks?
  2. Would you rather always leave with shoes that don’t match or earrings that don’t match?
  3. Would you rather be able to see other people’s futures or your own?
  4. Would you rather only be able to drink water or never be able to eat cookies?
  5. Would you rather have a unibrow or a completely full back that is covered in hair?
  6. Would you rather be unable to remember someone’s name every time or face every time?
  7. Would you rather blend into the background at all times or be the center of attention at all times?
  8. Would you rather be forced to pay twice as much for a plane ticket or be unable to fly ever again?
  9. Would you rather be able to fly or travel in time?
  10. Would you rather be able to change people’s hearts or change people’s minds?
  11. Would you rather have the power to walk through walls or x-ray vision?
  12. Would you rather be forced to marry someone you don’t love and someone who doesn’t love you?
  13. Would you rather go blind but always have beautiful hair or go bald and retain your vision?
  14. Would you rather be forced to sleepwalk or sleep talk?
  15. Would you rather have feet for hands or hands for feet?
  16. Would you rather have thumbs for your toes or pinky toes for your fingers?
  17. Would you rather be forced to swim across a river to get to work every day or climb a mountain to get to work every day?
Would You Rather Questions - Would you rather be forced to swim across a river to get to work every day or climb a mountain to get to work every day? | awkward would you rather questions | would you rather quiz | would you rather questions #deepquestions #affirmationoftheday #affirmationdaily
  1. Would you rather have an endless amount of energy or money?
  2. Would you rather have internet that is really snow or a phone signal that is really bad?
  3. Would you rather visit Mars or the Moon?
  4. Would you rather like your best friend’s foot or have a stranger lick your foot?
  5. Would you rather smell something bad that nobody else smells or always stink and not know why?
  6. Would you rather watch a movie in the theaters or at home?
  7. Would you rather spend all of your weekends inside or outside?
  8. Would you rather always say what you are thinking or never speak again?
  9. Would you rather be framed for a murder you didn’t do or frame your best friend for a murder that you did?
  10. Would you rather go to the deepest parts of the ocean or the outer reaches of space?
  11. Would you rather be able to change one event in your past or have a literal get out of jail free pass?
  12. Would you rather be able to dance the Tango or the Waltz?
  13. Would you rather learn every language on Earth or know how to talk to animals?
Would You Rather Questions - Would you rather learn every language on Earth or know how to talk to animals? | cute would you rather questions | would you rather animal questions | hard would you rather questions for couple #affirmationswork #selfquestion #affirmationweekly
  1. Would you rather be the fastest person on Earth or the strongest person on Earth?
  2. Would you rather have a GPS with a horrid signal or be forced to use physical maps?
  3. Would you rather have ears that record all sounds or eyes that record all vision?
  4. Would you rather cut your nails too short every time or not be able to own a pet?
  5. Would you rather bite your tongue on food or get a paper cut whenever you turn a page?
  6. Would you rather kiss a fish or a snake?
  7. Would you rather turn blue when you’re nervous or sweat when you’re anxious?
  8. Would you rather sneeze and cough at the same time or get the hiccups when you laugh?
  9. Would you rather be a cat or a dog?
  10. Would you rather forget everything you’ve ever heard or remember every conversation?
  11. Would you rather spend your life alone or with people you hate?
  12. Would you rather have your camera roll go public or your browser history go public
  13. Would you rather live in total isolation or be homeless in a major city?
  14. Would you rather change the results of the next election or alter the results of the one that just happened?
  15. Would you rather use a microwave for every meal or never again?
  16. Would you rather post an unflattering selfie to Instagram or get banned forever?
Would You Rather Questions - Would you rather post an unflattering selfie to Instagram or get banned forever? | would you rather questions about self | would you rather questions | would you rather pictures #selfimprovement #success #confidence
  1. Would you rather poop out of your mouth or eat out of your butt?
  2. Would you rather have grandpa’s clothes or your grandpa's hair?
  3. Would you rather give up tacos or pizza for the rest of your life?
  4. Would you rather wear a bra over your clothes or in the shower?
  5. Would you rather live on the streets for a week or spend one night with your ex?
  6. Would you rather have a car that could fly or the fastest internet ever?
  7. Would you rather have people think you’re a dog or have a dog that could actually talk?
  8. Would you rather say I love you to end every conversation or never again?
  9. Would you rather win the lottery but be forced to spend it in a day or have your salary tripled for the rest of your life?
  10. Would you rather tell when someone is lying forever or be able to lie without anyone figuring it out?
  11. Would you rather be able to control water or fire?
  12. Would you rather eat your nail clippings or hair trimmings?
  13. Would you rather be the star of a sitcom that gets canceled after the first season or a radio DJ who is mildly successful?
  14. Would you rather pay twice as much for your clothes or be forced to make all of them?
Would You Rather Questions - Would you rather pay twice as much for your clothes or be forced to make all of them? | would u rather questions dirty | would you rather quiz hard | would you rather love questions #selfconfidence #selfassurance #selfesteem
  1. Would you rather have an embarrassing birthmark on your butt or a pimple on your face?
  2. Would you rather be mistaken for a bad actor or your father?
  3. Would you rather wash your pets or your dishes with your tongue?
  4. Would you rather have your kitchen with everything you need but disorganized or a neat kitchen that is always missing one thing you need to complete your recipes?
  5. Would you rather never be able to use your phone’s camera again or your phone’s calling system again?
  6. Would you rather have your house be broken into and burglarized or your phone broken into with all of your information leaked to the general public?
  7. Would you rather be forced to text using only emojis or abbreviations?
  8. Would you rather be forced to wear black contacts to a job interview or be forced to get a bad tattoo?
  9. Would you rather be forced to drink everything using a coffee stir or a shot glass?
  10. Would you rather have a family that is super big or super small?
  11. Would you rather be forced to eat a cup of dirt or a cup of lawn clippings?
  12. Would you rather have a second set of eyes on the back of your head or poisonous fangs?
  13. Would you rather never be able to watch TV again or never be able to use YouTube again?
  14. Would you rather be homeless for around five years and then rich forever or always be in the lower middle class but never actually go homeless?
  15. Would you rather receive one big, flashy gift from someone or a bunch of small but meaningful gifts from someone?
Would You Rather Questions - Would you rather receive one big, flashy gift from someone or a bunch of small but meaningful gifts from someone? | best deep would you rather questions | meaningful would you rather questions | personal would you rather questions #affirmationmonthly #life #dailyaffirmations
  1. Would you rather sleep in the same clothes you have on during the day or be forced to sleep without blankets or pillows?
  2. Would you rather be forced to hibernate during the winter or be forced to go nocturnal during the winter?
  3. Would you rather grow three inches taller or never have to receive a single piece of spam mail ever again?
  4. Would you rather never go to a fun party ever again or be stuck with the cleanup at the best party ever?
  5. Would you rather always feel nauseous or always feel dizzy?
  6. Would you rather get silver at the Olympics or be the best hula-hooper of all time?
  7. Would you rather never receive another piece of mail or never receive another birthday card?
  8. Would you rather be forced to eat off the ground or be forced to eat all of your meals with your hands?
  9. Would you rather be forced to eat TV dinners forever or be forced to eat raw food forever?
  10. Would you rather be forced to spend a week with your worst enemy or never be allowed to see your best friend ever again?
  11. Would you rather blow up like a pufferfish when you feel threatened or bark like a small dog?
  12. Would you rather tell your ex you still are in love with them or kiss a horse?
  13. Would you rather discover the biggest diamond ever or the lost city of Atlantis?
  14. Would you rather spend the night in a landfill or be forced to face your biggest fear?
  15. Would you rather be able to see smells or taste colors?
Would You Rather Questions - Would you rather be able to see smells or taste colors? | philosophical would you rather questions | deep questions to ask in would you rather | sad would you rather questions #personaldevelopment #personalgrowth #education
  1. Would you rather be forced to eat cereal every day for the rest of your life or never be allowed to eat cereal ever again?
  2. Would you rather get attacked by a goose and possibly die or get attacked by a shark and live for sure?
  3. Would you rather be a world-famous singer or a world-famous dancer?
  4. Would you rather be the best President ever or the best athlete who ever lived?
  5. Would you rather be able to go through every traffic light ever or never have to wait for your food at a restaurant?
  6. Would you rather be in a total coma for ten years or have to live in jail for five years?
  7. Would you rather go to the beach alone or go on a cruise with all of your coworkers?
  8. Would you rather be raised by monkeys or by wolves?
  9. Would you rather be forced to make money on the streets by selling drugs or gambling?
  10. Would you rather have the hands of a baby or the neck of a giraffe?
  11. Would you rather be able to see noises or hear colors?
  12. Would you rather live in a world without technology or in a world without nature?
  13. Would you rather have the ability to fly or become invisible at will?
  14. Would you rather have a photographic memory or the ability to forget anything you want?
  15. Would you rather be stranded on a deserted island alone or with someone you can't stand?
  16. Would you rather be able to talk to space aliens or speak all human languages fluently?
  17. Would you rather live in a world with no music or live in a world with no clothes?
  18. Would you rather be able to control the weather or control the rotation of the planets?
  19. Would you rather be able to teleport anywhere in the world or have the ability to read people's thoughts?
  20. Would you rather be able to talk to the dead or talk to your future self?
  21. Would you rather never be able to taste food again or live in the sewer for the rest of your life?
  22. Would you rather be able to breathe underwater or walk through fire unscathed?
  23. Would you rather be able to cuddle a kitten anytime you want or play any musical instrument perfectly?
  24. Would you rather live in a house made of paper or a houseboat made of sponges?
deep would you rather questions for couples | crazy would you rather questions | random would you rather questions
  1. Would you rather be able to see 10 minutes into the future or have x-ray vision?
  2. Would you rather be the best athlete in the world or the smartest person in the world?
  3. Would you rather be able to cure all cancer or cure anyone who is blind?
  4. Would you rather have the power to heal anyone you touch or the power to bring any person back to life?
  5. Would you rather be a famous musician or king of your own country?
  6. Would you rather never have to sleep in a bed again or always have to sleep in a tree?
  7. Would you rather have the ability to time travel anywhere on Earth or teleport to any other solar system?
  8. Would you rather be able to talk to ghosts or be famous on social media?
  9. Would you rather be able to control your good dreams or control your scary nightmares?
  10. Would you rather have a photographic memory or the ability to read anyone's mind?
  11. Would you rather be able to breathe underwater for a year or breathe in outer space for a week?
  12. Would you rather live in a world without wine or a world without books?
  13. Would you rather be able to communicate with all animals or with inanimate objects?
  14. Would you rather have the power of telekinesis or the power of telepathy?
  15. Would you rather be able to change the past or change places with someone famous for a day?
  16. Would you rather be able to talk to anyone in any language or read their mind in any language?
  17. Would you rather be able to stop time for 5 years or stop crime forever?
  18. Would you rather be able to talk to animals or control artificial intelligence?
  19. Would you rather be able to talk to your 5-year-old self or your 95-year-old self?
  20. Would you rather be able to control the weather or control earthquakes?
  21. Would you rather be able to fly to the moon or have the strength to throw a football 200 yards?
  22. Would you rather be able to teleport anywhere in the world or be able to clone yourself?
  23. Would you rather live in a world with no running water or no internet?
  24. Would you rather be able to shape-shift into any animal or have the ability to turn invisible?
  25. Would you rather be able to breathe fire or shoot lasers from your nose?
  26. Would you rather live in a world where everyone was immortal and invisible, or everyone had to walk backward while singing a song that never ends?
  27. Would you rather be able to retire from your job when you’re 30 years old or live to be 200 years old?

Final Thoughts on Would You Rather Questions

In the end, would you rather questions are a great way for you to get to know someone better. The whole idea of these questions is to present you with an alternative to the traditional ways of getting to know someone.

If you want your children to participate, check out these 125 fun (and clean) would you rather questions for kids and these would you rather questions for teens.

would you rather questions for couples | emotional would you rather questions | would you rather quiz