73 Embarrassing Would You Rather Questions

Ever found yourself in a situation where the only way to break the ice or truly get to know someone is by asking them some hilariously awkward questions? That's where Embarrassing Would You Rather Questions come in! These are the kind of questions that make you squirm a little, giggle a lot, and sometimes, reveal more than you intended. They're a fantastic tool for sparking fun conversations and seeing how people think when faced with silly, cringe-worthy choices.

What Makes Embarrassing Would You Rather Questions So... Embarrassing?

Embarrassing Would You Rather Questions are all about presenting two equally, or sometimes surprisingly unequally, undesirable options. The goal isn't to find the "right" answer, but to explore the thought process behind choosing one awkward situation over another. They're popular because they're inherently funny and relatable. We've all had those moments where we wished the ground would swallow us whole, and these questions tap into that shared human experience. The importance of these questions lies in their ability to create laughter, build connections through shared discomfort, and reveal personality quirks in a lighthearted way.

People use these questions for a bunch of reasons. They're perfect for breaking the tension at parties, getting to know new friends, or even spicing up a long-term relationship. They can be used in casual get-togethers, icebreaker games for new teams, or even just as a way to pass the time with friends online. The beauty of them is their versatility – you can tailor them to your audience, making them as mild or as spicy as you like. Here's a breakdown of how they work:

You're presented with two scenarios.
You *must* choose one.
The scenarios are designed to be awkward, embarrassing, or downright silly.
The resulting discussion is often the best part!

Think of it like this:

The "Oh No!" Factor: Both options make you think, "Ugh, I really don't want to do either of those things!"
The "Which is Worse?" Game: You have to weigh the unpleasantness and decide which pill you're willing to swallow.
The Reveal: Your choice might tell people something about your fears, your sense of humor, or your priorities.

Awkward Social Situations

Would you rather accidentally send a naked selfie to your boss or have your most embarrassing text message read out loud at a family reunion?
Would you rather trip and fall in front of your crush or have your favorite song suddenly start playing loudly from your phone during a silent exam?
Would you rather have to sing karaoke in your underwear or have to wear a giant inflatable sumo suit for a whole day?
Would you rather burp the alphabet every time you speak or have to loudly confess your deepest secret to a stranger?
Would you rather have your entire browsing history displayed on a public billboard or have your diary read aloud by a celebrity?
Would you rather have to eat a plate of worms or have to kiss your least favorite person?
Would you rather have to announce your love for your celebrity crush to a crowded room or have to admit your worst habit to your entire school?
Would you rather have to wear socks with sandals to a formal event or have to speak with a squeaky voice all day?
Would you rather have a permanent unibrow or have to smell like onions for a week?
Would you rather have to dance uncontrollably every time you hear music or have to laugh hysterically at inappropriate times?
Would you rather accidentally call your teacher "Mom" or have your most embarrassing childhood photo go viral?
Would you rather have to wear a sign that says "I am a loser" or have to apologize to everyone you've ever met for something you didn't do?
Would you rather have to eat a spoonful of mayonnaise or have to lick a public doorknob?
Would you rather have to wear a toilet seat as a hat for a week or have to pretend to be a dog for a day?
Would you rather accidentally confess your crush to the wrong person or accidentally confess your biggest fear to your worst enemy?
Would you rather have to go to school with food in your teeth all day or have to wear a shirt inside out and backwards?
Would you rather have to moo like a cow every time you sneeze or have to quack like a duck every time you laugh?
Would you rather have to ask a stranger for their opinion on your outfit every hour or have to ask for directions even when you know where you're going?
Would you rather have to pretend to be a statue for an hour in a public place or have to walk around with your fly down for an hour?
Would you rather accidentally propose to your best friend's partner or accidentally reveal your secret talent to a rival?

Bodily Functions Gone Wild

Would you rather fart uncontrollably every time you're nervous or sweat profusely from your forehead every time you're happy?
Would you rather have hiccups that sound like a foghorn or sneezes that sound like a duck call?
Would you rather have your stomach growl loudly during every important meeting or have your nose whistle when you breathe?
Would you rather have to loudly announce your need to use the restroom or have to ask for permission before you can scratch an itch?
Would you rather have uncontrollable urges to lick things or have to sing everything you say?
Would you rather have a permanent case of bad breath that only you can't smell or have to wear a fake nose and glasses everywhere?
Would you rather have to pass gas every time you tell a lie or have to sweat glitter?
Would you rather have your ears pop loudly every time you speak or have your eyes water uncontrollably when you're thinking hard?
Would you rather have to burp in someone's face every time you disagree with them or have to hiccup every time you compliment someone?
Would you rather have to use a plunger as a microphone or have to wear a diaper in public?
Would you rather have to eat food that smells awful but tastes good or food that smells amazing but tastes awful?
Would you rather have to yodel every time you're surprised or have to clap your hands every time you're bored?
Would you rather have to spit every time you talk or have to drool when you're hungry?
Would you rather have to fart on demand or have to sweat on command?
Would you rather have to loudly clear your throat every five seconds or have to snort like a pig when you laugh?
Would you rather have to wear a colostomy bag for a day or have to wear a catheter for a day?
Would you rather have to taste your own earwax or have to smell your own armpit?
Would you rather have to lick your own elbow or have to lick a public toilet seat?
Would you rather have to wear a thong as a face mask or wear a bikini as a shirt?
Would you rather have to sing opera every time you have to ask a question or have to dance a jig every time you get an answer?

Embarrassing Fashion Choices

Would you rather have to wear a neon green spandex suit every day or have to wear a giant banana costume to work?
Would you rather have to wear a tutu and ballet slippers everywhere you go or have to wear a knight's armor for a week?
Would you rather have to wear mismatched socks every day or have to wear shoes that are two sizes too big?
Would you rather have to wear a shirt with your own embarrassing baby picture on it or have to wear a hat shaped like a giant hot dog?
Would you rather have to wear a sign that says "I have bad fashion sense" or have to ask people if your outfit looks okay every ten minutes?
Would you rather have to wear a wedding dress to a funeral or a tuxedo to a beach party?
Would you rather have to wear a full clown outfit for a month or have to wear a straitjacket for a week?
Would you rather have to wear a dress made of toilet paper or a suit made of trash bags?
Would you rather have to wear a furry animal costume of your least favorite animal or a giant inflatable chicken suit?
Would you rather have to wear a cape and a mask everywhere you go or have to wear a crown and a scepter?
Would you rather have to wear a shirt that says "I farted" or a shirt that says "I peed myself"?
Would you rather have to wear a skirt made of bandages or pants made of bubble wrap?
Would you rather have to wear a swimsuit in the middle of winter or a snowsuit in the middle of summer?
Would you rather have to wear mismatched shoes every day or have to wear a hat that's too small for your head?
Would you rather have to wear a sign that says "Ask me about my embarrassing moment" or have to wear a t-shirt with a giant embarrassing photo of yourself?
Would you rather have to wear a beekeeper's hat and gloves for a week or a pirate costume for a month?
Would you rather have to wear a giant inflatable sumo wrestler suit or a full knight's armor?
Would you rather have to wear a dress made of money or a suit made of chocolate?
Would you rather have to wear a giant red clown nose and big shoes or a silly wig and oversized glasses?
Would you rather have to wear a sign that says "I have a weird obsession" or wear a shirt that says "I'm a terrible dancer"?

Awkward Romantic Dilemmas

Would you rather accidentally text your crush about your crush on them or have your parents serenade you and your crush in public?
Would you rather have to confess your deepest romantic fantasy to your crush or have to admit your most embarrassing dating mishap to your crush's parents?
Would you rather have your ex show up at your date and start singing a love song to you or have your current partner reveal their secret crush on your best friend?
Would you rather have to give a public proposal that gets rejected or have to write a love letter that gets accidentally sent to your boss?
Would you rather have to sing a love song in a very bad voice to your crush or have to choreograph a romantic dance that you have to perform?
Would you rather have your entire dating history appear on a giant screen at a party or have your crush read your most embarrassing private messages?
Would you rather have to ask out your teacher or have to break up with someone you don't like in front of a huge crowd?
Would you rather have to propose with a ring pop or have to get married in a fast-food restaurant?
Would you rather have your parents plan your entire wedding or have your crush plan your entire breakup?
Would you rather have to wear a t-shirt that says "I'm single and ready to mingle" to your ex's wedding or wear a shirt that says "I still love my ex" to your current partner's birthday?
Would you rather have to admit you stalk your crush on social media or have to admit you accidentally used your crush's toothbrush?
Would you rather have to serenade your crush with a cheesy song or have to give them a piggyback ride to their house?
Would you rather have to confess your love to your crush using only interpretive dance or have to confess your love using only animal sounds?
Would you rather have to wear a sign that says "I'm looking for love" or have to hand out flyers with your dating profile?
Would you rather have to accidentally call your crush by your ex's name or accidentally call your crush by your pet's name?
Would you rather have to publicly declare your undying love for your crush even if they don't like you back or have to publicly declare your hatred for someone you secretly admire?
Would you rather have to get a tattoo of your crush's face or have to get a tattoo of your most embarrassing childhood memory?
Would you rather have to wear a wedding dress on your first date or wear a groom's suit for a casual outing?
Would you rather have to sing a breakup song to your crush or have to choreograph a proposal dance?
Would you rather have to admit you believe in soulmates or have to admit you've written a love poem about your crush?

Hypothetical Horrors

Would you rather have to fight a duck-sized horse or a horse-sized duck?
Would you rather be able to talk to animals but they all hate you or be able to fly but only an inch off the ground?
Would you rather have a permanent photographic memory of every embarrassing moment you've ever experienced or have no memory of anything that happened in the last 24 hours?
Would you rather have to wear a shirt made of sandpaper or a hat made of razor blades?
Would you rather be able to control the weather but it always rains on your parade or be able to teleport but you always arrive naked?
Would you rather have to eat a live scorpion or drink a glass of your own sweat?
Would you rather have to fight a thousand tiny ants or one giant ant?
Would you rather have a tail that wags uncontrollably when you're happy or ears that swivel when you're listening?
Would you rather have to live in a world where everyone speaks in rhyme or a world where everyone communicates through interpretive dance?
Would you rather have to fight a bear with a tiny spoon or a swarm of bees with only your breath?
Would you rather have to permanently smell like garlic or have to permanently taste everything like sour milk?
Would you rather have to constantly whisper everything you say or have to shout everything you say?
Would you rather have to live without your sense of taste or your sense of smell?
Would you rather have to fight a clown or a mime?
Would you rather have to wear a diaper for the rest of your life or have to wear a bib for the rest of your life?
Would you rather have to walk backwards for the rest of your life or hop everywhere on one foot?
Would you rather have to answer every question with "yes" or "no"?
Would you rather have to communicate with everyone through sign language or through opera singing?
Would you rather have to fight a shark with a pool noodle or a lion with a feather duster?
Would you rather have to eat a bowl of spiders or a bowl of cockroaches?

Just Plain Weird

Would you rather have to communicate with your pet through interpretive dance or have to have a conversation with your furniture?
Would you rather have to wear your pants on your head for a day or your shirt on your legs for a day?
Would you rather have to eat a sandwich made of your own hair or drink a smoothie made of your toenail clippings?
Would you rather have to name all your future children after types of cheese or types of vegetables?
Would you rather have to only eat food that is purple or food that is blue?
Would you rather have to sleep in a bathtub full of pudding or a bed made of mashed potatoes?
Would you rather have to give yourself a wedgie every hour or have to wear your underwear on the outside of your clothes?
Would you rather have to replace your hands with hot dogs or your feet with carrots?
Would you rather have to sing everything you do in a musical style or act out everything you do like a silent film?
Would you rather have to wear socks on your hands or gloves on your feet?
Would you rather have to talk like a robot or laugh like a hyena for a whole day?
Would you rather have to wear a t-shirt that says "I'm an alien" or a hat that says "I'm a potato"?
Would you rather have to fight a marshmallow or a piece of broccoli?
Would you rather have to wear a mustache made of real hair or a beard made of yarn?
Would you rather have to communicate with everyone using only emojis or using only pig latin?
Would you rather have to wear a giant novelty hat every day or a superhero cape everywhere you go?
Would you rather have to eat your school lunch off the floor or have to drink from the toilet?
Would you rather have to wear a sign that says "I'm a weirdo" or wear a t-shirt with a picture of a random stranger on it?
Would you rather have to sneeze glitter or hiccup bubbles?
Would you rather have to have a pet goldfish that sings opera or a pet hamster that tells dad jokes?

So there you have it! Embarrassing Would You Rather Questions are a fun, silly, and sometimes surprisingly revealing way to connect with people. Whether you're looking to spice up a game night or just get a good laugh, these questions are guaranteed to get people talking, squirming, and hopefully, having a blast. Just remember to play nice and don't ask anything that will *actually* hurt someone's feelings!