The Best Would You Rather Questions: The Ultimate List post image

The Best Would You Rather Questions: The Ultimate List


“Would You Rather” is a game that never gets old. Whether on a date to get to know someone, or in a long car ride to pass the time, it’s fun, often hilarious, thought-provoking, and always a good time.

It can be used in pretty much any situation and always create an “opening” for someone to overshare and reveal humiliating, hilarious, and shocking details about who they are.

This game, as crazy and silly as it might sound, can be a fun way to get people talking. You can use these questions in a group situation, when you’re alone with someone, or even via text!

MORE: Amazing Questions to Ask a Guy – The Only List You Need

Tip: always ask a follow up if someone reveals something particularly interesting. This sets you up to learn more about them. By asking something you are genuinely interested in you also set yourself up to win because you are more likely to have a genuine connection and conversation!

I am going to break this article down into a couple categories.

First, I will provide the best would you rather questions that apply “across the board.” Then, I will get into specific “naughty would you rather” questions to turn up the heat in a spicy dating situation, some outrageous questions to ask if you’re feeling bold, and some kind of personal ones to use when the moment is right.

Here we go…

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Best would you rather questions:

  • Would you rather be a fairy or a dinosaur?
  • Would you rather be fat or hairy?
  • Would you rather be skinny and die sooner or fat and live long?
  • Would you rather be a stupid person or a genius who was lonely?
  • Would you rather be lonely or sad?
  • Would you rather be healthy and poor or rich and sick?
  • Would you rather be a masochist or sadist?
  • Would you rather die fat or alone?
  • Would you rather be a social butterfly with no family or a homebody with a family?
  • Would you rather be married to someone you hate or alone?
  • Would you rather be the opposite sex for a day or be someone you hate for a day?
  • Would you rather be stuck on a roller coaster or in an elevator?
  • Would you rather be an adrenaline junkie or a complete hermit?
  • Would you rather die alone or in the arms of someone you hate?
  • Would you rather pee your pants or have to pee for 10 hours?
  • Would you rather throw up or have a stomach ache?
  • Would you rather be nice and unhappy or mean and happy?
  • Would you rather lie and be nervous about it or be honest and abandoned?
  • Would you rather be weird and happy or cool and sad?
  • Would you rather throw a football or kick a soccer ball?
  • Would you rather your mom or dad die?
  • Would you rather love and lose it or never love at all?
  • Would you rather be cheated on or be broken up with?
  • Would you rather have long hair that is damaged or short healthy hair?
  • Would you rather throw up for a day or be sick with pneumonia for a week?
  • Would you rather be late for an important meeting or late to your wedding?
  • Would you rather be famous but insecure or a nobody forever, but feel content with yourself?
  • Would you rather be weird or boring?
  • Would you rather be arrested for something you did not do and go to jail for 7 years, or go to jail for something you did do for life?
  • Would you rather fly or be able to be invisible?
  • Would you rather play video games for 2 days straight or jump out of a plane?
  • Would you rather go skydiving or bungee jumping?
  • Would you rather be a lifeguard or firefighter?
  • Would you rather be a police officer or be a firefighter?
  • Would you rather murder your best friend and get away with it or kill three random people and get arrested for it?
  • Would you rather be hated for who you are or loved for who you are not?
  • Would you rather be celebrated even though you lied or shamed for something you did not do?
  • Would you rather go into combat and die young or have a good life and avoid war?
  • Would you rather do an embarrassing photo shoot or be in fashion week?
  • Would you rather read or watch the news?
  • Would you rather go to clubs or bars?
  • Would you rather try a new food or be stuck with the same meal every day?
  • Would you rather eat at a restaurant or cook a meal at home?
  • Would you rather punch someone in the face or be punched in the face?
  • Would you rather be deaf or blind?
  • Would you rather never eat carbs for the rest of your life or never listen to music for the rest of your life?
  • Would you rather be unlucky in love or unlucky with money?
  • Would you rather get lost in the woods or lost in a dangerous city?
  • Would you rather give up Instagram or Google?
  • Would you rather your clothes always be too tight or too loose?
  • Would you rather be constantly itchy or constantly tired?
  • Would you rather have one talent you’re amazing at or a bunch of talents you’re mediocre at?
  • Would you rather have super fast wifi anywhere in the world or that your electronic devices never run out of batteries?
  • Would you rather look incredibly fit but be out of shape or be really in shape but look overweight?
  • Would you rather live somewhere really hot or super cold?
  • Would you rather be a cat or a dog?
  • Would you rather never have to work a day in your life and stay rich or never have to workout another day in your life and stay fit and in shape?
  • Would you rather have the ability to teleport or read minds?
  • Would you rather live in a mansion in the middle of nowhere or a tiny apartment in the best part of your favorite city?
  • Would you rather be rich or famous?
  • Would you rather look better in photos or in person?
  • Would you rather be too hot or too cold?
  • Would you rather live on a boat or in a trailer?
  • Would you rather work at a job you hate and make tons of money or a job you love and make very little money?
  • Would you rather live 100 years in the future or 100 years in the past?
  • Would you rather be an amazing artist or a math genius?
  • Would you rather be able to go back in time or be able to fly?
  • Would you rather cook at home or eat at a restaurant?
  • Would you rather die young and happy or die old and sad?
  • Would you rather lose everything but be happy or have a boring, mediocre life and never feel challenged or like you can grow?
  • Would you rather be a saint or a sinner?
  • Would you rather be a hero or a villain?
  • Would you rather be sadistic or too nice?
  • Would you rather be a really popular jerk in a small town or a really “trendy” hipster in a popular city?
  • Would you rather be artsy or business savvy?
  • Would you rather be a really good musician but have to suffer and never make it or be a horrible musician with zero talent and use vocalizers to make it?
  • Would you rather be Faulkner or Hemingway?
  • Would you rather be Britney Spears or Lorde?
  • Would you rather win an Oscar or win a Grammy?
  • Would you rather be Eminem or 21 Savage?
  • Would you rather be Carrie or Samantha?
  • Would you rather be with Mr. Big or Aiden?
  • Would you rather be a writer for TV or movies?
  • Would you rather be sadistic or too nice?
  • Would you rather be a model or an actress?
  • Would you rather be a soccer player or a volleyball coach?
  • Would you rather be a trendsetter who gets mocked or a follower who gets nothing special?
  • Would you rather have three of the worst years of your life followed by the best year of your life or four mediocre years?
  • Would you rather be 10 minutes late or 10 minutes early?

MORE: The Best Never Have I Ever Questions

Naughty Would You Rather Questions:

  • Would you rather throw away your life with drugs or become a sex addict?
  • Would you rather have sex with someone you hate or never have sex?
  • Would you rather have sex with a person you have zero attraction to who is faithful or a hot person who cheats?
  • Would you rather be an exhibitionist or a shy person?
  • Would you rather give a hickey or be given a hickey?
  • Would you rather love being naked but be kind of shamed for it or hate being naked and have people mock you for being a prude?
  • Would you rather cheat on someone you love or cheat because you are bored and pretending to be with someone?
  • Would you rather be a famous singer or never known for who you are?
  • Would you rather marry someone who loves a political figure you hate or someone with a religious belief you hate?
  • Would you rather have an abortion or gain 200 pounds?
  • Would you rather die a virgin or have a bunch of STDs?
  • Would you rather have a weird fetish or not have any fun?
  • Would you rather walk around naked in public or poop your pants in public?
  • Would you rather do porn or be poor?
  • Would you rather have sex with a “forbidden” person (i.e. a person in authority or some position of power) or have sex with someone you felt zero attraction to?
  • Would you rather look amazing naked but only decent in clothes, or amazing in clothes but not great naked?
  • Would you rather have a hot body and unattractive face or attractive face but and unattractive body?

MORE: The Best Questions to Ask to Get to Know Someone 

Outrageous Would You Rather Questions:

  • Would you rather be weird and have nothing to talk about or be overly talkative and feel like no one is interested in what you have to say?
  • Would you rather throw up on someone or accidentally get period blood on them?
  • Would you rather have pneumonia or the stomach flu?
  • Would you rather have to wear glasses or have no sense of smell?
  • Would you rather be a Disney character or an anime?
  • Would you rather have sex with an ugly person or a person with a lot of baggage?
  • Would you rather write a book or a screenplay?
  • Would you rather get bronchitis or the stomach flu?
  • Would you rather be on the news or never be able to watch TV?
  • Would you rather have fun on a date but get dumped or be in a relationship with someone you hate?
  • Would you rather know your future and never be surprised or have complete uncertainty?
  • Would you rather be sad but skinny or fat and happy?
  • Would you rather eat 12 bananas or 12 oranges?
  • Would you rather eat lunch or dinner forever?
  • Would you rather be thrown against a dumpster on fire or run into a war zone?
  • Would you rather have your entire house burned down or your best friend killed?
  • Would you rather kiss a frog or a fish?
  • Would you rather have a clown stalk you or a mermaid hit you in the face?
  • Would you rather be psycho and in a mental asylum or a lunatic and be in jail?
  • Would you rather lose your sense of taste or sense of smell?
  • Would you rather smell bad or have bad breath?
  • Would you rather not shower for a month or not have access to the internet for a month?

MORE: Crazy Truth or Dare Questions to Ask Your Friends 

Personal would you rather questions:

  • Would you rather lie and never get caught or be honest but accused of lying?
  • Would you rather never be jealous or never get angry?
  • Would you rather be accused of being a murderer even when you are innocent and end up arrested or a really insane person who kills people but gets away with it?
  • Would you rather have a strict upbringing or a really horrible one?
  • Would you rather be loved for who you are not or hated for who you are but at least people know the real you?
  • Would you rather be sad for a bit and lose a relationship you thought you wanted only to end up happier in the future, or would you rather be in a “fake” relationship that is decent and never go through heartbreak?
  • Would you rather have 3 really close friends, or 30 not so close friends?
  • Would you rather lose all your money or lose every photo you’ve ever taken?
  • Would you rather be happy or successful?

Related Links:

Amazing Would You Rather Questions 

10 Thought Provoking Would You Rather Questions

101 Impossible ‘Would You Rather’ Questions

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