73 Most Awkward Would You Rather Questions
73 Most Awkward Would You Rather Questions

We all know the game "Would You Rather." It's a fun way to pass the time and get to know people better. But sometimes, the questions go beyond just "Would you rather have a tail or wings?" and dive into territory that's a little, well, awkward. These are the Most Awkward Would You Rather Questions, designed to make you squirm, think, and maybe even laugh out loud at the sheer absurdity of it all.

The Wonderful World of Awkward Choices

What exactly makes a Would You Rather question "awkward"? It's all about creating a situation where both options are undesirable, bizarre, or force you to confront a personal discomfort. They aren't the simple "apple or orange" choices; these are the ones that make you pause, furrow your brow, and perhaps even break out in a sweat. The importance of these awkward questions lies in their ability to reveal hidden preferences, test your boundaries, and spark lively, often hilarious, discussions.

People love these questions for a bunch of reasons. They're great icebreakers at parties, perfect for long car rides, and excellent for getting to know your friends on a deeper, sillier level. Plus, they're just plain fun! Imagine the scenarios you have to picture:

  • Having to explain your embarrassing habit to your boss.
  • Dealing with a celebrity who misunderstands your life choices.
  • Navigating everyday situations with a very unusual appendage.

Here's a little peek at the kinds of things you might find yourself debating:

  1. Would you rather always have to sing everything you say or always have to dance everywhere you go?
  2. Would you rather have a permanent unibrow or permanently sticky hands?
  3. Would you rather sneeze confetti or burp bubbles?

Embarrassing Public Scenarios

  • Would you rather trip and fall in front of your crush every day or accidentally send a text meant for your best friend to your parents every day?
  • Would you rather have to loudly announce your arrival to every room you enter or have to leave every room with a dramatic exit?
  • Would you rather have your internal monologue broadcast to everyone around you or have your private thoughts displayed on a public billboard?
  • Would you rather have to wear socks with sandals everywhere you go for the rest of your life or have to wear a clown nose every day?
  • Would you rather your biggest embarrassing moment be replayed on national TV once a year or have a small, but noticeable, embarrassing sound effect play every time you do something slightly clumsy?
  • Would you rather have to apologize to inanimate objects you bump into or have to compliment strangers on their outfits every time you pass them?
  • Would you rather have a permanent blush that appears whenever you're nervous or have to constantly fidget with your hair?
  • Would you rather have to explain your entire life story to every new person you meet or have to answer one deeply personal question from every stranger?
  • Would you rather have your phone autocorrect every word to "pickle" or have your phone always read your texts aloud to anyone nearby?
  • Would you rather have to wear a superhero cape everywhere you go or have to wear a tiny tiara everywhere you go?
  • Would you rather accidentally call your teacher "Mom" or "Dad" in front of the whole class or accidentally wear your shirt inside out and backwards for a whole school day?
  • Would you rather have to speak in a fake accent for a month or have to wear mismatched shoes for a month?
  • Would you rather everyone you meet instantly know your most embarrassing nickname or have everyone you meet instantly know your most embarrassing childhood fear?
  • Would you rather have to do a silly dance every time you answer the phone or have to make a funny face every time someone takes your picture?
  • Would you rather have a laugh that sounds like a dying seagull or a sneeze that sounds like a foghorn?
  • Would you rather have to tell a bad joke every time you enter a conversation or have to hum a tune every time you leave a conversation?
  • Would you rather have your browser history shown to your family or have your social media comments read out loud at your next job interview?
  • Would you rather have to wear a t-shirt that says "I'm Awkward" or have to wear a hat that says "Ask Me Anything"?
  • Would you rather have to pretend to be a mannequin for 10 minutes every hour or have to strike a dramatic pose every time someone says your name?
  • Would you rather always smell faintly of broccoli or always have a small piece of food stuck in your teeth?

Bodily Oddities and Annoyances

  • Would you rather have to fart loudly every time you stand up or have to hiccup uncontrollably every time you try to speak?
  • Would you rather have incredibly itchy feet that you can't scratch for an hour every day or have a constant tickle in your throat that makes you want to cough?
  • Would you rather have to sweat profusely whenever you're slightly warm or have to shiver uncontrollably whenever you're slightly cold?
  • Would you rather have your ears constantly wiggle when you're happy or have your nose twitch when you're telling a lie?
  • Would you rather have to eat every meal with chopsticks that are too short or with a spoon that is too small?
  • Would you rather have to sneeze glitter every time you sneeze or have to cry rainbow tears every time you cry?
  • Would you rather have your fingernails grow an inch a day or your toenails grow an inch a day?
  • Would you rather have to chew everything with your mouth wide open or have to slurp every drink very loudly?
  • Would you rather have a voice that sounds like a chipmunk or a voice that sounds like a robot?
  • Would you rather have your hands always feel clammy or have your feet always feel sticky?
  • Would you rather have to blink with one eye at a time or have to stick out your tongue when you concentrate?
  • Would you rather have a permanently runny nose or a permanently watery eye?
  • Would you rather your hair change color randomly every day or your eye color change randomly every day?
  • Would you rather have to lick your elbow once a day or lick your own knee once a day?
  • Would you rather have a constant urge to hum a specific song or have a constant urge to tap your foot?
  • Would you rather have your belly button pop out and sing a little tune every time you're hungry or have your ears make a funny noise every time you're surprised?
  • Would you rather have to eat a spoonful of mustard every morning or eat a spoonful of mayonnaise every night?
  • Would you rather have a tiny, but annoying, mosquito always buzzing around your head or a tiny, but annoying, fly always trying to land on your food?
  • Would you rather have your breath smell like garlic 24/7 or your sweat smell like onions 24/7?
  • Would you rather have to constantly adjust your clothing or have to constantly smooth down imaginary wrinkles?

Weird Abilities and Superpowers

  • Would you rather be able to talk to animals but they always complain about everything or be able to fly but only at walking speed?
  • Would you rather be able to control the weather but only make it slightly annoying (e.g., constant drizzle, a persistent breeze) or be able to turn invisible but only for 5 seconds at a time?
  • Would you rather have super strength but your muscles ache constantly or have super speed but you always trip over things?
  • Would you rather be able to read minds but only hear people's thoughts about what they want to eat or be able to teleport but only to places you've never been before?
  • Would you rather be able to breathe underwater but you turn bright pink or be able to communicate with plants but they only talk about dirt?
  • Would you rather have the ability to perfectly mimic any sound but you can't control when it happens or have the ability to perfectly mimic any voice but you can only speak in that voice?
  • Would you rather be able to glow in the dark but only when you're embarrassed or be able to levitate but only when you're asleep?
  • Would you rather have the ability to make anyone laugh but you have to tell a terrible pun first or have the ability to make anyone cry but you have to sing a sad song?
  • Would you rather have super sensitive hearing but only be able to hear really annoying noises or have super vision but only be able to see in black and white?
  • Would you rather have the ability to control time but only by rewinding it by one second or have the ability to pause time but only for yourself?
  • Would you rather be able to shoot lasers from your eyes but they're really weak or be able to shoot webs from your hands but they're really sticky and hard to get off?
  • Would you rather have the ability to talk to inanimate objects but they're all incredibly sarcastic or have the ability to control electricity but only to power a tiny nightlight?
  • Would you rather be able to change your appearance to look like anyone but you have to keep the look for a week or be able to shapeshift but only into farm animals?
  • Would you rather have the ability to predict the future but only a minute before it happens or have the ability to erase memories but only your own?
  • Would you rather be able to control magnets but only to attract lint or be able to control fire but only to light a candle?
  • Would you rather have the ability to become a master of any musical instrument but you can only play terribly or have the ability to become a master of any sport but you always come in second place?
  • Would you rather be able to summon small, harmless creatures from your fingertips or be able to conjure an endless supply of slightly stale crackers?
  • Would you rather have the ability to fly but you can only go backwards or have the ability to run incredibly fast but you can only run in circles?
  • Would you rather be able to communicate with computers but they only speak in code or be able to communicate with robots but they only speak in riddles?
  • Would you rather have the power to make anyone instantly fall asleep but they wake up really grumpy or the power to make anyone instantly happy but they can't stop giggling?

Relationship Dilemmas

  • Would you rather have your parents read your text messages for the rest of your life or have your best friend announce all your secrets every time they see you?
  • Would you rather your significant other always tell you brutally honest, hurtful truths or always tell you elaborate, unbelievable lies?
  • Would you rather have to serenade your date with a song you wrote every time you go out or have to perform a dramatic interpretive dance about your day?
  • Would you rather your partner always steal your food or always borrow your clothes without asking?
  • Would you rather have to introduce every new person you meet as your "best friend forever" or have to say goodbye to everyone like you're never going to see them again?
  • Would you rather have your family constantly try to set you up with their friends' incredibly awkward children or have your friends constantly try to set you up with their own exes?
  • Would you rather your partner have a massive, embarrassing crush on your best friend or your best friend have a massive, embarrassing crush on your partner?
  • Would you rather have to tell your crush every single thing you've ever thought about them or have to pretend you've never met them?
  • Would you rather your parents always chaperone your dates or your younger sibling always tag along on your dates?
  • Would you rather have to wear matching outfits with your significant other every day or have to speak in rhyme to them constantly?
  • Would you rather your partner's parents visit unannounced every week or your partner's ex constantly show up at your doorstep?
  • Would you rather have to confess your most embarrassing dating mishap to your date within the first five minutes or have to pretend you're a completely different person on your first date?
  • Would you rather your friend always spill your deepest secrets to your significant other or your significant other always spill your friend's deepest secrets to you?
  • Would you rather have to ask your parents for permission before you go out or have to ask your siblings for their opinion on your outfit every day?
  • Would you rather have your pet always judge your dating choices or have your pet always interrupt your romantic moments?
  • Would you rather have to go on a double date with your parents or go on a date with your partner's most annoying relative?
  • Would you rather your partner always misunderstand your jokes or your partner always take your compliments the wrong way?
  • Would you rather have to introduce your pet as your primary love interest or have to introduce your significant other as your most cherished pet?
  • Would you rather have your family members always offer unsolicited dating advice or have your friends always try to "improve" your dating profile?
  • Would you rather have to break up with someone every week or have to go on a first date every week with someone you don't know at all?

Food and Drink Fiascos

  • Would you rather eat a bowl of live earthworms or drink a glass of lukewarm, unflavored pickle juice?
  • Would you rather have to eat every meal with your hands tied behind your back or have to drink every beverage through a ridiculously long straw?
  • Would you rather have your favorite food taste like dirt or have your favorite drink taste like vinegar?
  • Would you rather have to eat a whole raw onion like an apple or lick a dirty shoe?
  • Would you rather have to eat a sandwich made with toothpaste and pickles or a salad made with glitter and soap?
  • Would you rather have to drink a glass of water that's been sitting in the sun all day or a glass of milk that's been left out overnight?
  • Would you rather have to eat every single meal with a tiny fork and spoon or with chopsticks that are way too big?
  • Would you rather have to eat only bland, unseasoned boiled chicken for a year or eat only spicy, extremely hot chili peppers for a year?
  • Would you rather have to eat a dish made of grasshoppers and ants or a dish made of maggot cheese?
  • Would you rather have your coffee always be cold or your soup always be icy?
  • Would you rather have to eat a raw egg every morning or a handful of uncooked rice every night?
  • Would you rather have your favorite dessert taste like fish or your favorite savory dish taste like candy?
  • Would you rather have to eat everything with a plastic spoon that melts or with a fork that has bent prongs?
  • Would you rather have to eat a slice of pizza with anchovies and pineapple or a burger with jelly beans and pickles?
  • Would you rather have to drink a milkshake made with sardines and chocolate or a smoothie made with onions and strawberries?
  • Would you rather have to eat a bowl of cereal with milk that's gone sour or toast with butter that's rancid?
  • Would you rather have to eat a hot dog that's been dropped on the floor or a slice of cake that's been left outside in the rain?
  • Would you rather have to drink a glass of warm, flat soda or a glass of extremely fizzy, nearly exploding soda?
  • Would you rather have to eat a meal where every bite is a surprise flavor combination or a meal where every bite is a different texture?
  • Would you rather have your water always taste like bath soap or your juice always taste like hand sanitizer?

Everyday Annoyances Amplified

  • Would you rather have to whisper everything you say or have to shout everything you say?
  • Would you rather have to wear scratchy wool clothes all year round or wear clothes that are always slightly damp?
  • Would you rather have your shoes always be a size too small or your socks always be a size too big?
  • Would you rather have your car horn be replaced with a rubber chicken squeak or your doorbell be replaced with a loud opera singer?
  • Would you rather have to walk backward everywhere you go or have to hop on one foot everywhere you go?
  • Would you rather have every door you try to open be locked or have every chair you try to sit on be wobbly?
  • Would you rather have to answer every question with a question or have to answer every question with a riddle?
  • Would you rather have your phone battery die exactly when you need it most, every single time, or have your internet connection constantly drop every few minutes?
  • Would you rather have to carry a heavy, awkward object with you everywhere you go or have to wear a silly, attention-grabbing hat everywhere you go?
  • Would you rather have to use public restrooms that are always gross or have to use public transportation that's always overcrowded and smelly?
  • Would you rather have your remote control always be lost or have your keys always be misplaced?
  • Would you rather have to take a ridiculously long way to get anywhere or have to deal with constant, minor inconveniences?
  • Would you rather have your alarm clock go off at random times throughout the night or have your alarm clock be impossible to turn off without solving a complex puzzle?
  • Would you rather have to write everything down with a broken pencil or have to type everything on a keyboard with missing keys?
  • Would you rather have your computer always be incredibly slow or have your printer always run out of ink at the worst possible moment?
  • Would you rather have to deal with a persistent, annoying fly buzzing around you or a persistent, annoying mosquito biting you?
  • Would you rather have your reflection in mirrors always look slightly different or have your shadow move independently of you?
  • Would you rather have to take a cold shower every morning or a freezing cold bath every night?
  • Would you rather have to constantly adjust your glasses, even if you don't wear them, or have to constantly swat away imaginary bugs?
  • Would you rather have your everyday commute involve a series of minor, frustrating obstacles or have to participate in a short, mandatory, awkward social interaction with every stranger you pass?

So, the next time you're looking for a way to liven up a conversation or just want to see your friends squirm a little, whip out some of these Most Awkward Would You Rather Questions. You might be surprised at what you learn about yourself and the people around you, and you're guaranteed to have a good laugh along the way.

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