73 Embarrassing Would You Rather Questions
73 Embarrassing Would You Rather Questions

Let's talk about those tricky little questions that make you squirm a bit, but in a fun way. We're diving into the world of Embarrassing Would You Rather Questions, the kind that spark giggles, awkward silences, and sometimes, surprisingly deep thought. These aren't your average "pizza or tacos" questions; these are designed to put you on the spot and reveal a little bit more about how you'd handle a bizarre situation.

The Wonderful World of Awkward Choices

So, what exactly are Embarrassing Would You Rather Questions? Simply put, they're hypothetical scenarios that force you to choose between two less-than-ideal, often embarrassing, options. Think of them as little thought experiments that challenge your comfort zone. They're popular because they tap into our innate human curiosity about how we'd react in extreme or peculiar circumstances. Plus, they're a fantastic icebreaker or a way to inject some playful chaos into a gathering.

These questions are used in all sorts of settings. You might find them during:

  • Game nights
  • Road trips
  • Parties with friends
  • Even as a creative writing prompt!
The importance of these questions lies in their ability to foster communication and understanding , even if it's through a shared sense of mortification. They help us see how our friends or loved ones might think differently, and often, the sillier the question, the more genuine the reaction.

When playing "Would You Rather," it's all about the journey of choosing. Here's a quick guide:

  1. Listen carefully to both options.
  2. Imagine yourself in each situation. What would it feel like? What would happen?
  3. Don't overthink it too much! The point is to pick and then discuss why.
  4. Be prepared for your friends to tease you a little – that's part of the fun!
The goal isn't to find the "right" answer, but to enjoy the process of considering the absurd.

Personal and Peculiar Predicaments

  • Would you rather have to sing everything you say for a week or have to dance everywhere you go for a week?
  • Would you rather accidentally send a compromising text to your boss or accidentally call your crush while you're picking your nose?
  • Would you rather have your embarrassing childhood diary read aloud to your entire family or have your most embarrassing photo displayed on a billboard in your hometown?
  • Would you rather burp every time you speak or sweat profusely every time you're nervous?
  • Would you rather have to wear a sign that says "I believe in aliens" for a month or have to wear a giant fake mustache every day for a year?
  • Would you rather have your socks always be slightly damp or have your hair always be slightly greasy?
  • Would you rather have to tell your deepest secret to a stranger or have to reveal your biggest fear to your worst enemy?
  • Would you rather have to wear mismatched shoes every day or have to wear your shirt inside out every day?
  • Would you rather have a permanent blush that flares up when you're embarrassed or have to loudly announce "I'm feeling awkward" whenever you are?
  • Would you rather have to go grocery shopping in a full clown costume or have to ask for directions from a mime every time you're lost?
  • Would you rather have your internal monologue broadcasted on a loudspeaker for everyone to hear for one hour or have to act out all your thoughts as if they were a play for one hour?
  • Would you rather have to eat only bland, unseasoned food for a month or have to eat extremely spicy food for a week?
  • Would you rather have to confess your crush to someone who clearly isn't interested or have to admit you cheated on a test to your teacher?
  • Would you rather have to trip dramatically every time you enter a room or have to loudly announce "Oops, my bad!" after every minor mistake?
  • Would you rather have to smell faintly of rotten eggs for a week or have to have a faint, embarrassing tattoo appear on your forehead each day?
  • Would you rather have to speak in a squeaky voice for a day or have to have a constant, annoying tic that makes you wink uncontrollably?
  • Would you rather have to apologize profusely for things that aren't your fault or have to take credit for things you didn't do?
  • Would you rather have to wear a neon pink speedo everywhere you go in public or have to wear a full medieval knight's costume to work?
  • Would you rather have to sing karaoke off-key every time you're asked a question or have to do a silly dance whenever you're trying to be serious?
  • Would you rather have your entire family discover your secret embarrassing hobby or have your boss discover your secret embarrassing hobby?

Social Situations and Silly Scenarios

  • Would you rather accidentally flirt with your friend's parent or accidentally insult a respected elder?
  • Would you rather have to confess to your entire class that you still sleep with a stuffed animal or have to admit to your significant other that you sometimes talk to inanimate objects?
  • Would you rather get caught singing loudly and badly in a public restroom or get caught practicing dramatic poses in a shop window?
  • Would you rather have to wear roller skates everywhere for a day or have to wear flippers on your feet everywhere for a day?
  • Would you rather have to re-enact a romantic scene from a movie with a stranger or have to perform a silly skit for a group of toddlers?
  • Would you rather have to tell a joke that bombs horribly in front of a large audience or have to ask a very stupid question during an important meeting?
  • Would you rather have your embarrassing dating profile accidentally shared with your family or have your embarrassing dating profile accidentally shared with your colleagues?
  • Would you rather have to wear an oversized, bright yellow hat to every formal event for a year or have to wear a cape that trails everywhere you go for a year?
  • Would you rather have to publicly admit you're afraid of something silly like butterflies or have to publicly admit you don't know how to do something basic like tie your shoes?
  • Would you rather have to sneeze loudly and uncontrollably every time someone says your name or have to hiccup every time you try to explain something important?
  • Would you rather have to wear a t-shirt that says "I farted" to a job interview or have to wear a t-shirt that says "Ask me about my weird rash" on a first date?
  • Would you rather have to call your crush and sing them a love song that you made up on the spot or have to call your crush and confess your most embarrassing childhood memory?
  • Would you rather have to do an impression of a farm animal every time you're happy or have to do an impression of a robot every time you're sad?
  • Would you rather accidentally send a picture of your messy room to your boss or accidentally send a picture of yourself in pajamas to your crush?
  • Would you rather have to participate in a pie-eating contest where you're forced to get messy or have to participate in a public talent show where you're terrible?
  • Would you rather have to wear oven mitts on your hands for a week or have to wear swimming goggles on your eyes for a week?
  • Would you rather have to do a dramatic interpretive dance to explain a simple concept or have to sing a made-up song to answer any question?
  • Would you rather have your most embarrassing dream revealed in front of your friends or have your most embarrassing thought revealed in front of your family?
  • Would you rather have to ask every barista for "a cup of your finest hot bean juice" or have to ask every store clerk for "your most magnificent treasure"?
  • Would you rather have to loudly declare your love for a random stranger or have to loudly declare your dislike for a random stranger?

Food Fiascos and Flavorful Fails

  • Would you rather have to eat a bowl of mayonnaise for breakfast every day for a month or have to eat a bowl of raw onions for dinner every day for a week?
  • Would you rather have to drink a glass of pickle juice before every meal or have to eat a spoonful of mustard after every meal?
  • Would you rather have to lick a stranger's shoes or have to eat a fly that lands on your food?
  • Would you rather have to eat a ghost pepper and then sing a song or have to eat a whole lemon and then do a cartwheel?
  • Would you rather have to wear a bib made of lettuce to every fancy dinner or have to wear a chef's hat that's too small every day?
  • Would you rather have to eat all your meals with chopsticks, even soup, or have to eat all your meals with only a spoon, even steak?
  • Would you rather have to give a speech about your favorite food while only being allowed to use hand gestures or have to write a poem about your least favorite food while only being able to use your feet?
  • Would you rather have to drink a glass of raw egg every morning or have to eat a bite of expired milk every night?
  • Would you rather have to eat everything you normally would, but only if it's bright blue, or have to eat everything you normally would, but only if it's shaped like an animal?
  • Would you rather have to pretend to be a chef and cook a meal for your friends using only ingredients from a vending machine or pretend to be a world-class wine taster and describe the taste of tap water?
  • Would you rather have to eat a spoonful of dirt or have to eat a spoonful of earwax?
  • Would you rather have to announce every food you're about to eat by roaring like a lion or have to announce every food you're about to eat by squeaking like a mouse?
  • Would you rather have to wear a hat made of broccoli to every important event or have to wear shoes made of breadsticks to every important event?
  • Would you rather have to only eat food that is green for a week or have to eat food that is purple for a week?
  • Would you rather have to make a sandwich using only ingredients you find in your trash can (safely!) or have to make a cake using only ingredients you find in your bathroom cabinet (safely!)?
  • Would you rather have to drink a glass of your own sweat or have to drink a glass of someone else's sweat?
  • Would you rather have to eat a raw onion like an apple or have to eat a whole clove of raw garlic like a pill?
  • Would you rather have to be force-fed a plate of your least favorite food by a stranger or have to force-feed a plate of your least favorite food to a stranger?
  • Would you rather have to wear a t-shirt that says "I love Brussels Sprouts" on the front and "I hate Pizza" on the back or have to wear a t-shirt that says "I ate too much" on the front and "My stomach hurts" on the back?
  • Would you rather have to drink a glass of blended sardines or have to eat a handful of uncooked pasta?

Physical and Peculiar Performances

  • Would you rather have to walk around on your hands for an hour every day or have to hop on one foot for an hour every day?
  • Would you rather have to wear oven mitts on your hands for a whole week or have to wear large clown shoes on your feet for a whole week?
  • Would you rather have to sing opera loudly in public every time you need to ask a question or have to do a dramatic cartwheel every time you need to leave a room?
  • Would you rather have to wear a full squirrel costume for a day or have to wear a full banana costume for a day?
  • Would you rather have to tell everyone you meet that you are a secret agent or have to tell everyone you meet that you are an alien?
  • Would you rather have to sneeze glitter every time you laugh or have to cry tiny confetti every time you're sad?
  • Would you rather have to wear a shirt that constantly plays annoying music or have to wear shoes that randomly squeak very loudly?
  • Would you rather have to do a robot dance every time you're happy or have to do a silly jig every time you're angry?
  • Would you rather have to give a standing ovation to everything you see or have to applaud every time someone speaks?
  • Would you rather have to wear a t-shirt that says "I'm a terrible dancer" and then have to dance badly in public, or wear a t-shirt that says "I can't sing" and then have to sing badly in public?
  • Would you rather have to wear sunglasses indoors at all times or have to wear a hat indoors at all times?
  • Would you rather have to speak in a baby voice for a day or have to speak in a pirate voice for a day?
  • Would you rather have to pretend to be a statue for an hour in a busy public place or have to pretend to be an animal for an hour in a busy public place?
  • Would you rather have to wear a sign that says "I love cheese" around your neck for a week or have to wear a sign that says "I hate Mondays" around your neck for a week?
  • Would you rather have to hiccup uncontrollably for a day or have to yawn uncontrollably for a day?
  • Would you rather have to do a dramatic reenactment of your day every evening or have to sing a summary of your day every evening?
  • Would you rather have to wear a rubber chicken on your head for a day or have to wear a rubber duck on your head for a day?
  • Would you rather have to loudly declare "I'm a magnificent dancer!" and then dance poorly or loudly declare "I'm a brilliant singer!" and then sing poorly?
  • Would you rather have to wear a cape that is made of toilet paper or have to wear a crown that is made of tinfoil?
  • Would you rather have to do a silly walk every time you go to the bathroom or have to do a funny face every time you answer the phone?

Workplace Woes and Professional Pains

  • Would you rather have your boss catch you napping at your desk or have your boss catch you singing loudly to yourself?
  • Would you rather have to wear a novelty tie every day for a month or have to wear mismatched socks every day for a month?
  • Would you rather have to answer all work emails in rhyme or have to respond to all work calls with a dramatic monologue?
  • Would you rather have your colleagues overhear you practicing your terrible karaoke rendition of a work song or have them overhear you practicing your silly office dance routine?
  • Would you rather have to bring in a plate of your least favorite food for the office potluck or have to wear a t-shirt with a funny, embarrassing slogan on it to work?
  • Would you rather have to confess to your entire team that you still sleep with a teddy bear or have to confess to your entire team that you've never made a bed?
  • Would you rather have your most embarrassing childhood photo displayed in the office kitchen or have your most embarrassing social media post shared with your coworkers?
  • Would you rather have to ask for a raise by singing a song you wrote about your hard work or have to ask for a raise by doing a silly dance?
  • Would you rather have to wear a funny hat every day for a week or have to wear oversized novelty glasses every day for a week?
  • Would you rather have your boss accidentally see you wearing pajamas to a virtual meeting or have your boss accidentally see you trying on ridiculous outfits in the background?
  • Would you rather have to confess that you're afraid of the office printer or have to confess that you think the water cooler talks too much?
  • Would you rather have to wear a t-shirt that says "I'm the office comedian" and then tell corny jokes or wear a t-shirt that says "I'm the office chef" and then bring in questionable food?
  • Would you rather have to greet every coworker with a handshake and a silly catchphrase or greet every coworker with a high-five and a funny noise?
  • Would you rather have to whisper all your important work instructions or shout all your unimportant work instructions?
  • Would you rather have to wear a name tag that says "Ask me anything... but I might not know the answer" or wear a name tag that says "World's Best Employee... maybe"?
  • Would you rather have to give a presentation entirely in mime or give a presentation entirely in song?
  • Would you rather have your personal embarrassing playlist accidentally play during a team meeting or have your personal embarrassing voice memos accidentally play during a team meeting?
  • Would you rather have to ask the office IT person to help you with a very basic, embarrassing tech problem or ask the office janitor for help with a very personal, embarrassing hygiene issue?
  • Would you rather have to wear a sign that says "I make the best coffee... probably" or wear a sign that says "I'm really good at finding snacks"?
  • Would you rather have to confess that you sometimes talk to your plants at your desk or confess that you secretly judge everyone's stapler usage?

Embarrassing Would You Rather Questions are a fantastic way to lighten the mood, spark conversation, and learn a little something about the people around you. They remind us that it's okay to be a little silly, a little awkward, and to laugh at ourselves. So next time you're looking for a way to shake things up, break out some of these cringe-worthy, hilarious, and thought-provoking questions. You might be surprised at what you discover!

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