150 Best Would You Rather Questions to Embarrass Friends and Spark Fun Conversations

Are you ready to turn up the fun and hilarity at your next gathering? “Would you rather” questions can be the perfect way to challenge your friends and spark unforgettable moments. But why settle for mundane queries when you can unleash some truly embarrassing ones?

These playful prompts not only lighten the mood but also reveal surprising truths about your pals. Dive into this list of hilarious and cringe-worthy scenarios that will leave everyone laughing and blushing. Get ready to create memories that will have your friends talking for years to come!

Best Would You Rather Questions to Embarrass Friends and Spark Fun Conversations

Would You Rather: Have to sing everything you say for a week in front of your friends?

Option 1: Yes, and they have to join in!

Option 2: No, I’ll stick to speaking normally.

Would You Rather: Accidentally send a personal text to the entire group chat?

Option 1: Yes, and own it with a funny follow-up.

Option 2: No, I’d rather keep my secrets safe.

Would You Rather: Walk around with a giant sign that says your most embarrassing moment?

Option 1: Yes, and let everyone ask about it!

Option 2: No, I’ll keep that in the vault.

Would You Rather: Slip and fall in front of your crush while out with friends?

Option 1: Yes, and make a joke about it afterward.

Option 2: No, I prefer to maintain my cool.

Would You Rather: Have to wear a clown costume to your next friend’s gathering?

Option 1: Yes, and entertain everyone with balloon animals.

Option 2: No, I’d rather stick to my regular clothes.

Would You Rather: Share your most cringeworthy childhood photo during a group dinner?

Option 1: Yes, and narrate the story behind it!

Option 2: No, I’ll keep that photo hidden forever.

Would You Rather: Mispronounce a common word in front of your friends for a whole month?

Option 1: Yes, and make it a part of my new vocabulary!

Option 2: No, I’d rather not sound silly.

Would You Rather: Have your childhood diary read aloud in front of everyone?

Option 1: Yes, and provide commentary as it’s read!

Option 2: No, I’d rather not relive those moments.

Would You Rather: Accidentally wear your clothes inside out for an entire day with friends?

Option 1: Yes, and pretend it’s the latest fashion trend.

Option 2: No, I’d rather not risk the awkwardness.

Would You Rather: Be the butt of a joke for an entire game night?

Option 1: Yes, and laugh along with everyone.

Option 2: No, I prefer to be the one telling the jokes.

Would You Rather: Have to recite your most embarrassing secret in a sing-along?

Option 1: Yes, and make it a catchy tune!

Option 2: No, I’ll keep that to myself.

Would You Rather: Wear mismatched socks and shoes to a party and own it?

Option 1: Yes, and challenge everyone to do the same!

Option 2: No, I’ll stick to matching my outfit.

Would You Rather: Forget the punchline of a joke you just told, leaving everyone hanging?

Option 1: Yes, and make up a silly reason for it.

Option 2: No, I’d rather not leave people confused.

Would You Rather: End up dancing awkwardly in front of your friends during a silent moment?

Option 1: Yes, and turn it into a spontaneous dance-off!

Option 2: No, I’d rather avoid that cringe.

Would You Rather: Have to eat a food you hate while everyone watches and teases?

Option 1: Yes, and make a big dramatic show of it.

Option 2: No, I’ll choose to skip the meal instead.

See Also – Ultimate Collection of 150 Cringe-Worthy Would You Rather Questions

Would You Rather Questions to Embarrass Friends at Parties

Looking to spice up your next gathering? “Would You Rather” questions can be the perfect icebreaker! Choose ones that tickle the funny bone while pushing the boundaries of embarrassment, like “Would you rather sing karaoke in a chicken costume or dance like nobody’s watching in a colander?” Laughter and lighthearted…

Would You Rather: Share an embarrassing childhood story in front of everyone at the party?

Option 1: Tell everyone about the time you wore your clothes backward to school.

Option 2: Reveal your most cringeworthy crush moment to the group.

Would You Rather: Dance like no one is watching for an entire song?

Option 1: Do the chicken dance in front of everyone.

Option 2: Break out into the Macarena and get everyone to join you.

Would You Rather: Have to sing karaoke with a voice that sounds like a goat?

Option 1: Sing a love ballad off-key.

Option 2: Perform a rap song with exaggerated hand gestures.

Would You Rather: Wear a funny costume that you picked out in middle school?

Option 1: Dress as a giant banana.

Option 2: Show up in a superhero outfit with a cape.

Would You Rather: Accidentally send a flirty text to the wrong person?

Option 1: Send it to your crush.

Option 2: Send it to your parents.

Would You Rather: Have to give a toast while wearing a silly hat?

Option 1: Wear a giant foam finger.

Option 2: Sport a pirate hat with an eye patch.

Would You Rather: Trip and fall while walking into the party?

Option 1: Spill your drink all over yourself.

Option 2: Knock over a decoration on your way in.

Would You Rather: Get caught singing loudly in the bathroom?

Option 1: Sing a Disney song.

Option 2: Belt out a boy band classic.

Would You Rather: Have a voice crack while telling a joke?

Option 1: Tell a dad joke that falls flat.

Option 2: Mess up the punchline and laugh awkwardly.

Would You Rather: Show your most embarrassing selfie to the group?

Option 1: Share one from a bad hair day.

Option 2: Reveal one from a messy food moment.

Would You Rather: Have to wear mismatched shoes for the rest of the night?

Option 1: Wear one flip-flop and one high heel.

Option 2: Sport one sneaker and one sandal.

Would You Rather: Accidentally say a celebrity’s name instead of your date’s?

Option 1: Call your date by your ex’s name.

Option 2: Mix up their name with a famous movie star.

Would You Rather: Spill a secret about a friend while trying to impress others?

Option 1: Reveal their most embarrassing moment.

Option 2: Disclose their biggest fear in front of everyone.

Would You Rather: Do an impression of your least favorite teacher?

Option 1: Mimic their voice in a funny way.

Option 2: Imitate their mannerisms exaggeratedly.

Would You Rather: Have to tell a corny pun every time someone asks you a question?

Option 1: Use a pun about food.

Option 2: Rely on a pun about animals.

See Also – Ultimate Collection of Cringe-Worthy Would You Rather Questions to Test Your Limits

Creative Would You Rather Questions to Embarrass Friends in a Group Setting

Looking to spice up your next gathering? Try some creative “Would You Rather” questions designed to embarrass your friends! From choosing between singing karaoke in a silly costume or sharing an awkward childhood story, these questions will spark laughter and playful teasing, ensuring memorable moments and light-hearted fun for everyone…

Would You Rather: Sing karaoke in front of a large crowd dressed as a clown?

Option 1: Yes, and embrace the silliness!

Option 2: No, I’d rather not humiliate myself like that.

Would You Rather: Accidentally send a romantic text to your boss?

Option 1: Yes, I’d laugh it off!

Option 2: No way, that’s too embarrassing!

Would You Rather: Walk around with toilet paper stuck to your shoe for an entire day?

Option 1: Sure, it’s a great conversation starter!

Option 2: No, that would be mortifying!

Would You Rather: Have a loud, embarrassing ringtone go off during a quiet meeting?

Option 1: Yes, I’d make it a fun moment!

Option 2: No, I’d die of embarrassment!

Would You Rather: Do a silly dance in a public place for a minute?

Option 1: Absolutely, let’s get the crowd involved!

Option 2: Not a chance, I’d rather be invisible!

Would You Rather: Forget the name of someone you just met while introducing them?

Option 1: Yes, I could laugh it off later!

Option 2: No, that would be mortifying!

Would You Rather: Wear mismatched shoes to a formal event?

Option 1: Yes, I’d rock the quirky look!

Option 2: No, I need to look presentable!

Would You Rather: Trip and fall in front of your crush?

Option 1: Yes, at least it would be memorable!

Option 2: No, that would be too embarrassing!

Would You Rather: Have to recite a cringy poem you wrote in high school?

Option 1: Sure, it’s a blast from the past!

Option 2: No, I’d rather keep that secret!

Would You Rather: Have everyone at a party know your most embarrassing secret?

Option 1: Yes, let’s get it out in the open!

Option 2: No, that’s a hard pass!

Would You Rather: Give an impromptu speech about your most embarrassing moment?

Option 1: Yes, it could be a funny story!

Option 2: No, I’d rather stay quiet!

Would You Rather: Wear a silly hat for a week straight?

Option 1: Absolutely, I could make it a trend!

Option 2: No, I’d feel ridiculous!

Would You Rather: Have to eat a food you absolutely hate in front of everyone?

Option 1: Sure, at least it’ll be entertaining!

Option 2: No, that’s too much torture!

Would You Rather: Get caught singing in the shower by your roommates?

Option 1: Yes, I’d own it!

Option 2: No, that’s too embarrassing!

Would You Rather: Share a photo of your most embarrassing hairstyle on social media?

Option 1: Yes, let’s embrace the past!

Option 2: No, that’s a no-go for me!

See Also – Funny and Embarrassing Would You Rather Questions to Make You Laugh

Hilarious Would You Rather Questions to Embarrass Friends on Social Media

Dive into a world of laughter with hilarious ‘Would You Rather’ questions designed to embarrass your friends on social media! These playful prompts can spark uproarious debates, revealing silly secrets and quirks. Whether it’s choosing between wearing a tutu to work or singing in public, get ready for unforgettable moments…

Would You Rather: Share an embarrassing childhood photo of yourself on social media for a week?

Option 1: Post a picture of you in your most awkward school outfit.

Option 2: Share a video of you singing your favorite song poorly.

Would You Rather: Wear a ridiculous costume in public for a day?

Option 1: Dress as a giant hot dog.

Option 2: Go out in a unicorn onesie.

Would You Rather: Have to post an embarrassing status update every day for a month?

Option 1: “I still sleep with my stuffed animal.”

Option 2: “I can’t function without my morning dance party!”

Would You Rather: Text your crush an embarrassing autocorrect fail?

Option 1: “I can’t wait to see you and your cat!”

Option 2: “I love your face… I mean your place!”

Would You Rather: Participate in a TikTok dance challenge that you’re terrible at?

Option 1: Attempt the latest viral dance trend.

Option 2: Create your own silly dance and post it online.

Would You Rather: Get caught singing in the shower by a friend?

Option 1: Sing your favorite cheesy pop song.

Option 2: Belt out a classic from a musical.

Would You Rather: Wear socks with sandals for a week?

Option 1: Choose neon colors with stripes.

Option 2: Go for fuzzy animal-print socks.

Would You Rather: Have to retell an embarrassing story about yourself at a party?

Option 1: Share the time you tripped during a school presentation.

Option 2: Describe your most awkward date ever.

Would You Rather: Leave a voice message for your friend where you accidentally say something silly?

Option 1: Confess your love for a fictional character.

Option 2: Sing a commercial jingle at the top of your lungs.

Would You Rather: Post a selfie with a goofy filter every day for a week?

Option 1: Use the one that turns you into a baby.

Option 2: Choose the one with the big dog ears and tongue.

Would You Rather: Accidentally send a meme meant for your best friend to your mom?

Option 1: Send a meme about embarrassing moments.

Option 2: Share a meme about bad cooking skills.

Would You Rather: Share your most embarrassing moment on social media?

Option 1: The time you accidentally called your teacher “Mom.”

Option 2: When you thought you were on mute during a video call and sang loudly.

Would You Rather: Post a video of you trying to cook something that goes hilariously wrong?

Option 1: Attempt to bake a cake and it collapses.

Option 2: Try to flip a pancake and it lands on the ceiling.

Would You Rather: Wear a shirt that says “I’m a total dork” for a week?

Option 1: Include a picture of a cartoon character doing something silly.

Option 2: Have a list of your most embarrassing hobbies.

Would You Rather: Have to confess a silly secret to everyone in a group chat?

Option 1: Admit that you still sleep with a nightlight.

Option 2: Reveal that you sometimes talk to your pets like they understand you.

See Also – Ultimate Collection of 150 Hilarious Would You Rather Questions for Fun

Would You Rather Questions to Embarrass Friends During Game Night

Game night just got a whole lot more entertaining with ‘Would You Rather’ questions designed to embarrass your friends! Picture your pals squirming as they choose between outrageous scenarios, like singing in a public place or wearing an embarrassing costume. These playful prompts spark laughter and unforgettable moments, making your…

Would You Rather: Have to sing everything you say for a whole day?

Option 1: Yes, I’ll be a Broadway star!

Option 2: No way, I can’t carry a tune!

Would You Rather: Wear a silly costume to work/school every day for a month?

Option 1: Absolutely, I love to stand out!

Option 2: No, I’d die of embarrassment!

Would You Rather: Have to share your most embarrassing moment with the group?

Option 1: Bring it on, I’m an open book!

Option 2: No chance, I’m keeping that secret!

Would You Rather: Spend a day with your crush dressed as a chicken?

Option 1: Yes, I’d make them laugh!

Option 2: No, that would be too humiliating!

Would You Rather: Post a cringy childhood photo online for all to see?

Option 1: I’m ready for the likes!

Option 2: Not a chance, that’s a no-go!

Would You Rather: Talk like a baby in public for an hour?

Option 1: Sure, that’ll be hilarious!

Option 2: No way, that’s too embarrassing!

Would You Rather: Be caught talking to yourself in a mirror?

Option 1: Whatever, I’m just practicing!

Option 2: I’d be mortified!

Would You Rather: Have to dance in front of the group with no music?

Option 1: Yes, I’ll make up my own moves!

Option 2: No, I’d rather hide!

Would You Rather: Call your best friend by the wrong name for the rest of the night?

Option 1: That’ll be funny!

Option 2: Yikes, I’d feel so bad!

Would You Rather: Wear mismatched socks in a formal setting?

Option 1: Totally, it’ll be my quirky signature!

Option 2: No way, I need to look perfect!

Would You Rather: Have to give a speech about your most embarrassing moment?

Option 1: I’d embrace it and make it funny!

Option 2: Absolutely not, I’d freeze up!

Would You Rather: Have to read your last text message aloud to everyone?

Option 1: Bring it on, it could be funny!

Option 2: No, that could be awkward!

Would You Rather: Go a week without showering or brushing your teeth?

Option 1: I can handle it for the laughs!

Option 2: No, I’d rather not!

Would You Rather: Share a ridiculous secret talent with the group?

Option 1: Yes, I’ll entertain them!

Option 2: No, I’d rather keep it hidden!

Would You Rather: Have to wear a giant foam finger everywhere you go for a day?

Option 1: Absolutely, I’ll be the center of attention!

Option 2: No way, I’d feel so silly!

See Also – 150 Hilarious and Cringe-Worthy Would You Rather Challenges

Funny Would You Rather Questions to Embarrass Friends in Public

Looking to spice up your next gathering? Try “Would You Rather” questions designed to embarrass your friends in public! Imagine the laughter as they choose between wearing a tutu for a day or singing loudly in a crowded café. These playful prompts guarantee unforgettable moments and plenty of giggles—perfect for…

Would You Rather: Sing your heart out in public karaoke while wearing a chicken suit?

Option 1: Yes, and dance along!

Option 2: No, but I’ll play the air guitar instead.

Would You Rather: Get caught doing the floss dance in a serious meeting?

Option 1: Absolutely, I’ll own it!

Option 2: No way, I’d rather sit in silence.

Would You Rather: Speak only in rhymes for a whole day around your friends?

Option 1: Yes, that sounds fun!

Option 2: No, I value my sanity too much.

Would You Rather: Accidentally call your teacher “Mom” in front of the whole class?

Option 1: Yes, and then apologize dramatically!

Option 2: No, I’d rather just stay quiet.

Would You Rather: Wear socks with sandals for an entire week?

Option 1: Bring it on, I’ll rock that look!

Option 2: No, I’d rather wear mismatched shoes.

Would You Rather: Post an embarrassing childhood photo on social media?

Option 1: Sure, let’s relive the glory days!

Option 2: No, I’d rather keep it hidden forever.

Would You Rather: Have to do a silly walk every time you enter a room?

Option 1: Yes, it’ll be hilarious!

Option 2: No, I’ll stick to my normal stride.

Would You Rather: Get stuck in an elevator with a person who only talks in puns?

Option 1: Yes, let the wordplay begin!

Option 2: No, I’d rather take the stairs.

Would You Rather: Wear a sign that says “I love pineapple on pizza” in a pizza restaurant?

Option 1: Absolutely, I’ll embrace it!

Option 2: No, I’d rather keep my preferences secret.

Would You Rather: Have to recite a cringy poem you wrote in middle school?

Option 1: Yes, I’ll share my artistic talent!

Option 2: No, I would rather keep it locked away.

Would You Rather: Do your best impression of a famous celebrity in a crowded place?

Option 1: Yes, I’ll go big or go home!

Option 2: No, I’d rather stay under the radar.

Would You Rather: Get your entire group of friends to wear matching outfits for a day?

Option 1: Yes, let’s make it a fashion statement!

Option 2: No, I’d rather wear what I want.

Would You Rather: Get caught lip-syncing to a cheesy love song in public?

Option 1: Yes, I’ll give it my all!

Option 2: No, I’d rather keep my lips sealed.

Would You Rather: Share a fun fact about yourself that’s super embarrassing?

Option 1: Sure, I’m an open book!

Option 2: No, I’d rather keep it to myself.

Would You Rather: Have your phone autocorrect every text to something embarrassing for a day?

Option 1: Yes, let the chaos ensue!

Option 2: No, I’d rather avoid that disaster.

See Also – 150 Hilariously Awkward Would You Rather Questions to Challenge Your Comfort Zone

Would You Rather Questions to Embarrass Friends in a Road Trip Scenario

Road trips are the perfect setting for laughter and unforgettable memories, especially when you unleash a round of “Would You Rather” questions designed to embarrass your friends. Imagine asking, “Would you rather sing karaoke at a gas station or wear a silly costume for the next mile?” The giggles are…

Would You Rather: Share an embarrassing childhood story with the group?

Option 1: Tell everyone about your first crush and how you messed it up.

Option 2: Reveal the most ridiculous thing you did to impress someone in school.

Would You Rather: Sing your least favorite song at a rest stop?

Option 1: Belt out a cheesy pop song with the windows down.

Option 2: Perform a dramatic rendition of a classic ballad.

Would You Rather: Wear a silly hat for the entire trip?

Option 1: Sport a bright, oversized sombrero.

Option 2: Rock a neon feathered boa.

Would You Rather: Accidentally send a cringe-worthy text to the wrong person?

Option 1: Send a message meant for your best friend to your parents.

Option 2: Share a flirty text with the group chat instead of your crush.

Would You Rather: Do an impersonation of someone in the car?

Option 1: Imitate your friend’s most embarrassing moment.

Option 2: Pretend to be a famous celebrity in a ridiculous way.

Would You Rather: Get caught doing an awkward dance in public?

Option 1: Break out into the worm at a gas station.

Option 2: Do the chicken dance in front of strangers.

Would You Rather: Accidentally mix up your drink with someone else’s?

Option 1: Take a big sip of a beverage that tastes like vinegar.

Option 2: Drink someone’s super spicy soda by mistake.

Would You Rather: Share the most embarrassing thing in your search history?

Option 1: Reveal a Google search for “how to impress my crush.”

Option 2: Disclose a search for weird animal facts.

Would You Rather: Get a bad haircut while on the trip?

Option 1: Rock a mullet for the rest of the journey.

Option 2: Sport bright pink highlights inadvertently.

Would You Rather: Lose a game of truth or dare in front of the group?

Option 1: Wear your clothes backward for the rest of the day.

Option 2: Share an embarrassing secret about your last date.

Would You Rather: Find out your favorite snack is actually a weird flavor?

Option 1: Devour a bag of pickle-flavored chips.

Option 2: Enjoy a chocolate that tastes like bacon.

Would You Rather: Make a spontaneous stop to take a silly photo?

Option 1: Pose with a giant roadside attraction statue.

Option 2: Take a goofy group selfie in front of a fast-food restaurant.

Would You Rather: Have to wear mismatched clothes for the entire trip?

Option 1: Pair polka dots with stripes.

Option 2: Combine plaid with floral patterns.

Would You Rather: Attempt to tell a joke that totally flops?

Option 1: Try to tell a joke about dad puns that nobody laughs at.

Option 2: Share a cringe-worthy knock-knock joke that falls flat.

Would You Rather: Accidentally spill a drink all over yourself in the car?

Option 1: Drench yourself with soda while taking a sip.

Option 2: Spill water all over your lap during a bumpy ride.

See Also – 150 Hilariously Embarrassing Would You Rather Questions to Make You Blush

Spicy Would You Rather Questions to Embarrass Friends in a Truth or Dare Challenge

Spicing up your Truth or Dare game? Try these hilarious “Would You Rather” questions designed to embarrass your friends! From choosing between singing a cheesy pop song in public or dancing like nobody’s watching, these playful dilemmas will spark laughter and light-hearted teasing, ensuring your game night is unforgettable and…

Would You Rather: Share your most embarrassing childhood memory with the group?

Option 1: Reveal the time you peed your pants in public.

Option 2: Admit you had an imaginary friend until you were 12.

Would You Rather: Sing a song in a silly voice in front of everyone?

Option 1: Belt out “Let It Go” from Frozen.

Option 2: Croon “Baby Shark” like a professional.

Would You Rather: Have everyone read your text messages out loud?

Option 1: Let them read your cringe-worthy crush texts.

Option 2: Share your most embarrassing autocorrect fails.

Would You Rather: Wear a silly costume for a week?

Option 1: Dress as a giant banana.

Option 2: Sport a chicken suit everywhere you go.

Would You Rather: Post the most embarrassing photo of yourself on social media?

Option 1: Share your awkward school picture.

Option 2: Post that time you had a terrible haircut.

Would You Rather: Do a goofy dance in front of everyone?

Option 1: Attempt the worm.

Option 2: Try to moonwalk and fail miserably.

Would You Rather: Talk in rhymes for the next hour?

Option 1: Speak like Dr. Seuss.

Option 2: Only use words that end in “ing.”

Would You Rather: Have to wear mismatched socks for a month?

Option 1: Sport polka dots with stripes.

Option 2: Mix patterns that clash horrendously.

Would You Rather: Share your worst pickup line ever?

Option 1: Reveal the one that got you laughed at.

Option 2: Tell the line that got you ghosted.

Would You Rather: Tell an embarrassing secret about yourself?

Option 1: Confess to a cringey habit.

Option 2: Share a time you totally embarrassed yourself in public.

Would You Rather: Have a ridiculous nickname that everyone calls you?

Option 1: Be known as “Silly Socks.”

Option 2: Go by “Captain Cringe.”

Would You Rather: Do impressions of everyone in the room?

Option 1: Imitate their laugh.

Option 2: Mimic their most common phrase.

Would You Rather: Have to wear a sign that says something embarrassing for the day?

Option 1: “I still sleep with a stuffed animal.”

Option 2: “I can’t cook to save my life!”

Would You Rather: Get caught in an embarrassing moment on video?

Option 1: Trip and fall in front of a crowd.

Option 2: Slip while trying to dance.

Would You Rather: Have to tell your most embarrassing story to a stranger?

Option 1: Share the tale of your worst date.

Option 2: Reveal how you embarrassed yourself in front of a crush.

See Also – Top 150 Fun and Embarrassing Would You Rather Questions for Laughter

Would You Rather Questions to Embarrass Friends Over Dinner

Dinner parties can be a blast, especially when you spice things up with “Would You Rather” questions! Imagine the laughter as you ask friends to choose between wearing a clown suit for a month or singing karaoke in public. These playful dilemmas are perfect for light-hearted embarrassment and unforgettable memories!

Would You Rather: Have to sing everything you say for a day?

Option 1: Yes, and in a high-pitched voice!

Option 2: No, but I can only speak in rhymes!

Would You Rather: Accidentally send a text about someone to that person?

Option 1: Yes, and it’s super embarrassing!

Option 2: No, but it’s a heartfelt confession!

Would You Rather: Wear your clothes backward for an entire week?

Option 1: Yes, and explain it to everyone!

Option 2: No, but wear mismatched shoes!

Would You Rather: Have a clown follow you around for a month?

Option 1: Yes, and do tricks all the time!

Option 2: No, but have a mime instead!

Would You Rather: Trip and fall in front of your crush?

Option 1: Yes, and spill your drink all over them!

Option 2: No, but accidentally call them by the wrong name!

Would You Rather: Have to dance every time you hear music?

Option 1: Yes, in the most awkward way possible!

Option 2: No, but only using the robot dance!

Would You Rather: Have to tell a silly joke that nobody laughs at?

Option 1: Yes, and repeat it until someone does!

Option 2: No, but have to make a pun about it!

Would You Rather: Lose your phone in a public restroom?

Option 1: Yes, and have to retrieve it yourself!

Option 2: No, but drop it in a fountain instead!

Would You Rather: Have to wear a ridiculous hat for a year?

Option 1: Yes, and never take it off!

Option 2: No, but wear clown shoes every day!

Would You Rather: Get caught singing in the shower by your roommate?

Option 1: Yes, and they record it!

Option 2: No, but they join in with the worst voice!

Would You Rather: Be stuck in an elevator with someone you dislike?

Option 1: Yes, and have to make small talk!

Option 2: No, but the lights go out!

Would You Rather: Have to read your most embarrassing diary entry aloud?

Option 1: Yes, and do it in front of your friends!

Option 2: No, but have to share a secret crush!

Would You Rather: Be mistaken for a celebrity and have to act like them?

Option 1: Yes, and do embarrassing impressions!

Option 2: No, but have to wear their signature outfit!

Would You Rather: Accidentally spill food on yourself during dinner?

Option 1: Yes, and have to wear a bib for the rest of the meal!

Option 2: No, but have to share the food with everyone else!

Would You Rather: Have a bad haircut for a month?

Option 1: Yes, and have to take selfies every day!

Option 2: No, but wear a silly wig instead!

See Also – Hilarious and Embarrassing Would You Rather Questions to Ignite Laughter

Unique Would You Rather Questions to Embarrass Friends at a Sleepover

At your next sleepover, kick off the laughter with unique “Would You Rather” questions designed to tease and embarrass your friends! Picture them choosing between wearing a silly costume for a week or singing karaoke in front of strangers. These playful dilemmas spark fun debates and unforgettable memories that will…

Would You Rather: Have to sing everything you say for a day?

Option 1: Sing in a high-pitched voice.

Option 2: Sing in a deep, booming voice.

Would You Rather: Wear a ridiculous costume to school for a week?

Option 1: A giant chicken suit.

Option 2: A superhero outfit with a cape.

Would You Rather: Accidentally send a flirty text to your crush?

Option 1: Send it to your parents instead.

Option 2: Send it to your best friend.

Would You Rather: Have to do a silly dance every time you enter a room?

Option 1: The chicken dance.

Option 2: The moonwalk.

Would You Rather: Get stuck in a never-ending group hug with your friends?

Option 1: With everyone wearing clown outfits.

Option 2: While singing a lullaby.

Would You Rather: Have to narrate your life in a dramatic voice for a day?

Option 1: Like a soap opera star.

Option 2: Like a nature documentary narrator.

Would You Rather: Lose a bet and have to wear your pajamas in public?

Option 1: To a fancy restaurant.

Option 2: To a busy shopping mall.

Would You Rather: Walk around with a giant sign that says something embarrassing about yourself?

Option 1: “I dance like no one’s watching, but everyone is.”

Option 2: “I still sleep with a stuffed animal.”

Would You Rather: Eat a spoonful of mayonnaise in front of everyone?

Option 1: While wearing a blindfold.

Option 2: While doing a silly dance.

Would You Rather: Have to talk in rhymes for an entire day?

Option 1: With a British accent.

Option 2: In a silly voice.

Would You Rather: Show up to a party with mismatched shoes?

Option 1: One sneaker and one flip-flop.

Option 2: One sandal and one high heel.

Would You Rather: Have to tell an embarrassing story about yourself?

Option 1: In front of your crush.

Option 2: In front of your parents.

Would You Rather: Be stuck wearing a clown wig for a week?

Option 1: While also sporting face paint.

Option 2: While having to honk a horn every hour.

Would You Rather: Have a friend record you singing in the shower?

Option 1: And post it on social media.

Option 2: And play it at the next sleepover.

Would You Rather: Mix up your friends’ names while introducing them?

Option 1: Call them all by your ex’s name.

Option 2: Call them all by your favorite cartoon character’s name.