100 Hardest Would you rather Questions For Adults That You Can’t Answer

Wanna Know Someone Better? You got these questions! These questions forces people to think and help you understand their true nature.

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All of us, at one point or another, have experienced the moment when we have to choose between the devil and the deep sea. And while most of the time, the situation leaves us panicked and perplexed, it is in moments like these that reveal who we truly as human beings are. It makes us think about what we value the most; be it love or money, family or job, or even just coffee over tea or brownies over doughnuts. Such as:

  • Would you rather receive a present that you don’t like or give a present that you don’t like?
  • Would you rather fly in a plane with head outside window or swim with eyes completely shut?
  • Would you rather want your team to win every tournament or win every match against a rival team?
  • Would you rather eat without getting fat or have free food subscription for life?
  • Would you rather time travel or travel world around 80 days?

Therefore we have prepared you a list of questions that you can ask your friends to have some fun and deep conversation. You can also ask these questions to yourself and you might be able to understand your own choices a little bit better.

Serious Would you rather Questions

Looking to get to know someone better in a much lesser time?

You may ask a person some serious question like “Would you rather believe the best of people or accept them as they are?”

Answer to the above question may lead to serious ice-breaking philosophical discussion such as what is kinder? To believe the best of people and burden them with a nobility beyond their endurance capacity or to accept people as they are because it makes them more comfortable?

Here we have listed down a few of those serious yet interesting questions, which you can choose and make your conversation far more compelling as well as attractive. Pick your favorite serious questions and get ready to jump into a philosophical chit chat with your friend(s):

  1. Would you rather be born in the past or be born in the future?
  2. Would you rather lose all your money or lose all your memories?
  3. Would you rather know your date of death or your cause of death?
  4. Would you rather lose your ability to speak or your ability to listen?
  5. Would you rather appear late to an event or early to an event?
  6. Would you rather not get old physically or not get old mentally?
  7. Would you rather have more time or have more money?
  8. Would you rather be really rich or be really famous?
  9. Would you rather be the most intelligent person or the most liked person?
  10. Would you rather be absolute master of one field or be mediocre in multiple fields?
  11. Would you rather erase your memory or have an exceptional memory recall?
  12. Would you rather host 20 people at your place or spend your time at someone else’s place?
  13. Would you rather have birthdays every three months or have birthdays every three years?
  14. Would you rather have skin that changes color based on your emotions or tattoos appear all over your body depicting what you did yesterday?
  15. Would you rather receive novelty socks as a present or receive expired chocolates?
  16. Would you rather receive a present you don’t like or give someone a present they don’t like?
  17. Would you rather have unlimited battery life on all of your devices or have free internet access wherever you go?
  18. Would you rather listen to a 10 minutes voice note or read 500 words message on whatsapp?
  19. Would you rather have to sew all your clothes or grow your own food?
  20. Would you rather be extremely rich and live 100 years ago or be poor but live today?
  21. Would you rather spend your life as a single person or be a part of an arranged marriage?
  22. Would you rather change your eye color or your hair color?
  23. Would you rather have a family of 15 children or never be able to have children at all?
  24. Would you rather have the ability to read minds or have the ability to move things with your mind?
  25. Would you rather give up air conditioning and heating for your entire life or give up the Internet for the rest of your life?
  26. Would you rather die before or after your spouse?

Funny Would you rather Questions

Rather than being serious, it’s always enthralling to continue a conversation with some humorous and funny questions. For example, Would you rather fly in a plane with your head outside the window or swim with your eyes completely shut?

While answering such a funny question you might end up imagining your head amidst clouds in an altitude and temperature unimaginable. You may laugh at each other for looking like a white-walker for preferring head outside window flight or otherwise you or your friends will end up in shark’s mouth for swimming with eyes completely shut.

Hence we have listed down few chucklesome debriefing questions to ask your colleague, your friend, or an anonymous sitting next to you in the metro. Hop down and go through the listed questions below:

  1. Would you rather be allowed one murder or allowed one robbery?
  2. Would you rather fly like a bird or swim like a fish for the rest of your life?
  3. Would you rather have tangled hair or blemished skin?
  4. Would you rather have the key that opens any door or the password signs-in any account?
  5. Would you rather want to never pay for air travel or never pay for food?
  6. Would you rather lose your eyes lashes or eye brows?
  7. Would you rather not be able to laugh or not be able to cry?
  8. Would you rather play with every toy in a department store overnight or eat all the food in a supermarket all day?
  9. Would you rather sit in the garden for an hour with no coat in winters or sit on the roof all day in summers?
  10. Would you rather wear an ugly dress with lights all over it or wear underwear on top of your pants?
  11. Would you rather spend a night in a stable in your swimming costume or spend a night in an igloo without a coat?
  12. Would you rather wear a birthday cap every day for a year or wear a paper crown to bed every night?
  13. Would you rather wake up to find you’ve sprouted antlers from your head or wake up to find you’ve sprouted a donkey’s tail?
  14. Would you rather have a snowball fight or build a snowman with melting snow?
  15. Would you rather shop online and have the sites crash on you every 10 minutes or shop in the stores and queue for hours?
  16. Would you rather get a paper cut every time you turn a page or bite your tongue every time you eat?
  17. Would you rather be 3 Feet  short or 7.5 feet tall?
  18. Would you rather buy 10 things you don’t need every time you go shopping or always forget the one thing that you need the most when you go to the supermarket?
  19. Would you rather wear the same socks for a month or the same underwear for a week?
  20. Would you rather find a lizard or a rat in your bed?
  21. Would you rather walk to work without footwear or drive to work in reverse?

Entertaining Would you rather Questions

Would you rather want your team to win every tournament or win every match against a rival team?

Now, if you or your circle is a sports enthusiast, you might loudly say BOTH! It’s a tough pick where you want your team to win every match against a rival and ended up winning the tournament as well. However, there might be some who would say winning the tournament matters even if it takes to lose against rivals. Honestly, consider Brazil vs Argentina or England vs Australia in Ashes makes this question even more entertaining.

Not interested in sports and want more entertaining questions to find about your new friend’s interests? Or about one’s intrigues relevant to the current fad or about fashion trends? Just a heads up though since enlisted questions can help you make enough memories alongside knowing the answers to queries that have spinning in your head for some time. There you go:

  1. Would you rather sing your favorite song or dance to it?
  2. Would you rather eat only Christmas cake every day for a week or wear your Christmas sweater on the hottest day of the year?
  3. Would you rather spend holiday with tons of presents and be alone or spend Christmas with family who give no presents?
  4. Would you rather have pointy ears like an elf or have a bright red nose like Rudolph?
  5. Would you rather wake up to one enormous present or wake up to a lots of little presents?
  6. Would you rather take amazing selfies but look terrible in all other photos or be photogenic everywhere but in your selfies?
  7. Would you rather have a tennis lesson from Rafael Nadal or a football lesson from Lionel Messi?
  8. Would you rather watch nothing but documentaries or nothing but horror movies?
  9. Would you rather spend the day with your favorite athlete or your favorite movie star?
  10. Would you rather sing karaoke or write nonstopfor an hour?
  11. Would you rather have Angelina Jolie’s lips or Emma Watson’s hair?
  12. Would you rather have Taylor Swift’s voice or Britney Spear’s dance moves?
  13. Would you rather listen to the songs of your least favorite band on a loop for a day or never listen to any music at all for a year?
  14. Would you rather cast Thomas Cruise or Chris Evans in your movie?
  15. Would you rather listen to kpop for the rest of your life or only be able to watch one Netflix show for the rest of your life?
  16. Would you rather be as strong as Captain Marvel or run as fast as The Flash?

FOOD. Would you rather…

Would you rather eat without getting fat at all or have a free food subscription for life?

If I am to answer, I’d say free food subscription for life. Imagine all your favorite food is FREE. ABSOLUTELY FREE. Your favorite brownies, pizzas, wings, cheese sticks, and whatnot. But I can hear you saying I’d rather afford all the food and would happily prefer eating without getting fat at all.

Anyways, more food questions are below. So in case if your high school friends coming over after a long time, and you don’t know about their food choices anymore? Or are you about to go on a date without a clue of one’s likes and dislikes? Leap into these optional questions, know about your friend’s preferences, and be foodies together.

  1. Would you rather have brownie with coffee or have biscuit with tea?
  2. Would you rather eat gingerbread cookies with too much oil or eat mince pies with salt instead of sugar?
  3. Would you rather wash up after a meal for 20 people or cook a meal for 20 people?
  4. Would you rather take a sleigh ride through raspberry jelly or climb down a burning chimney made of chocolate?
  5. Would you rather eat cheesecake with nutcracker or eat chicken with teaspoon?
  6. Would you rather never eat watermelon ever again or be forced to eat watermelon with every meal?
  7. Would you rather eat cake with gravy on top or have whipped cream on your beef?
  8. Would you rather drink Coke or water your entire life?
  9. Would you rather eat only cheese burger for a year or not eat any cheese burger for five years?
  10. Would you rather go vegan for a year or only eat meat and dairy for a year?
  11. Would you rather never drink your favorite shake for the rest of your life or only drink your favorite shake?
  12. Would you rather give up hot coffee or cold coffee forever?
  13. Would you rather eat eggs for every meal for a year or be able to eat whatever you wanted, but only once every 2 days?
  14. Would you rather eat raw garlic or raw onion?
  15. Would you rather eat every meal with ketchup or with mustard?
  16. Would you rather give up eating cookies or give up eating crackers?
  17. Would you rather eat brownies with mayo or a tart dipped in thousand island sauce?
  18. Would rather have Nutella brownie or chocolate lava cake every day for dessert?
  19. Would you rather eat spinach cookies or spinach ice cream?
  20. Would you rather live in a world without coffee or a world without tea?
  21. Would rather be forced to eat with no utensils for every meal, or never eat desserts again?
  22. Would you rather eat KFC or McDonalds for the rest of your life?

Would you rather “Travel” Questions

Would you rather time travel or travel around the world in 80 days?

Sometimes, would you rather end up giving such a difficult choice that I wish I could say both? I want time travel as well as to travel the world in 80 days or maybe more. Secretly, I wish to travel and get hold of time travel so that I keep on rewinding that time and keep on going back there.

All of us love to travel from time to time, and most probably each one has dreamed about traveling the whole world and know more places side by side, meet new people and get on some adventure. Besides these dreams, it is necessary to know about the choices of the bunch of people traveling with you, in order to make the trip a success and of course, more memorable. Ask the listed questions with your traveling buddies before you get on the road and get some recommendations.

  1. Would you rather visit the mountains or visit the sea?
  2. Would you rather drive through sunset or sunrise?
  3. Would you rather spend a weekend at a penthouse in the city with no friends or at a cottage in the country with no food?
  4. Would you rather travel by train or by airplane?
  5. Would you rather go ice-skating in boots that are too small or watch a movie without sound?
  6. Would you rather capture a sunset or sunrise?
  7. Would you rather drive along the sea shore or amidst snow-capped peaks?
  8. Would you rather spend a night in the desert with temperatures at 50C or in Arctic with temperature of -50C?
  9. Would you rather live on the beach or in the forest?
  10. Would you rather climb Mount Everest or swim in the Pacific Ocean?
  11. Would rather go to an amusement park or water park?
  12. Would you rather travel through time or travel through space?
  13. Would you rather travel to New Zealand or Australia
  14. Would you rather forget to pack clean undergarments when traveling or forget to pack your makeup?
  15. Would you rather be on a helicopter for two hours, or on an airplane?

Surely this is the end of the question list here, but we hope, the questions were enough to know someone or enhance your abilities to brainstorm in order to better understand the other’s sensibility or life choices. Entertaining and funny questions, we hope, gave you a good laughing time.

Asking such ice-breaking questions isn’t necessarily a healthy conversation starter but also boosts your confidence to make new friends with a similar mindset and is a good way to bring about a smile or laughter on your colleague’s face. You may even try asking one random question from each category every day with your spouse, best friend, girlfriend/ boyfriend, or maybe your flatmate or colleague and learn more about each other well.

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