73 Obscure Would You Rather Questions

Ever get tired of the same old "would you rather have wings or be able to breathe underwater?" questions? If you're nodding along, then you're ready to dive into the wonderfully weird world of Obscure Would You Rather Questions. These aren't your average thought-starters; they're designed to make you pause, chuckle, and maybe even sweat a little as you try to pick between two equally baffling, hilarious, or surprisingly difficult scenarios.

What Are Obscure Would You Rather Questions and Why Do We Love Them?

So, what exactly are Obscure Would You Rather Questions? Think of them as the quirky, offbeat cousins of regular "would you rather" games. Instead of simple choices, they present you with outlandish situations that are hard to imagine, but once you do, they become strangely compelling. They might involve silly superpowers, peculiar daily routines, or even slightly unsettling circumstances. The beauty of these questions lies in their ability to bypass the obvious and tap into our imagination, forcing us to consider the unexpected consequences of bizarre choices.

These questions are popular because they break the mold and inject a dose of pure fun and unpredictability into conversations. They're not about finding the "right" answer; they're about the journey of trying to pick one. They encourage creativity and can lead to some epic debates and hilarious explanations. They're perfect for breaking the ice at parties, livening up road trips, or just having a good laugh with friends. The importance of Obscure Would You Rather Questions lies in their ability to spark genuine, unexpected thought and generate memorable moments.

They challenge our comfort zones.
They offer a fresh perspective on decision-making.
They are a fantastic way to get to know someone's sense of humor and thought process.

You can use them in a variety of ways:

As a game: Simply take turns asking each other the questions and discuss your choices.
As conversation starters: Introduce a few obscure questions to liven up a lull in the chat.
For creative writing prompts: Imagine yourself in these scenarios and write a short story about what happens.

Everyday Oddities

Would you rather have a tiny, invisible dragon that constantly whispers bad advice into your ear, or a perpetually squeaky shoe that only you can hear?
Would you rather have to sing everything you say in a terrible opera voice, or have every sneeze sound like a duck quacking?
Would you rather find a perfectly ripe avocado in your pocket every single day, or always find a quarter in your shoe?
Would you rather have your nose run constantly but only with glitter, or have your ears clog up with popcorn kernels every morning?
Would you rather be able to talk to squirrels but they only gossip about your neighbors, or be able to communicate with plants but they only complain about the weather?
Would you rather have a personal cloud that follows you and rains lightly whenever you're sad, or a personal sunshine that follows you and always feels warm even in winter?
Would you rather have your reflection in mirrors occasionally wink at you, or have your shadow sometimes wave at passersby?
Would you rather every time you laugh, you hiccup uncontrollably for five minutes, or every time you yawn, you bark like a dog?
Would you rather have to wear socks on your hands for the rest of your life, or wear oven mitts on your feet?
Would you rather have your internal monologue narrated by a cartoon character of your choice, or have all your thoughts translate into interpretive dance?
Would you rather have your dreams be perpetually about being chased by giant marshmallows, or have your dreams always be about trying to find a matching pair of socks?
Would you rather have to iron your clothes with a waffle iron, or cook your food with a hair straightener?
Would you rather have your pet understand you perfectly but only respond in bad dad jokes, or have your appliances talk to you but only to complain about their jobs?
Would you rather have to eat every meal with chopsticks, even soup, or have to eat every meal with a tiny plastic spoon?
Would you rather have your urine smell like freshly baked cookies, or have your sweat smell like your favorite flower?
Would you rather have a permanent, faint smell of old books about you, or a faint smell of a freshly mowed lawn?
Would you rather have to start every sentence with "Actually," or end every sentence with "…allegedly"?
Would you rather have a personal theme song play every time you enter a room, or have sound effects accompany your every movement?
Would you rather have your hair always be slightly damp, or have your clothes always feel a little too tight?
Would you rather be able to perfectly mimic any animal sound but only when you're trying to be serious, or be able to perfectly fold any piece of laundry but only when you're in a hurry?

Fantastical Feats

Would you rather be able to instantly teleport anywhere, but only to places you've seen in a dream, or be able to fly, but only at the speed of a brisk walk?
Would you rather have the ability to talk to inanimate objects but they're all incredibly rude, or have the ability to communicate with ghosts but they only talk about their unfinished errands?
Would you rather be able to control time but only in increments of five seconds forward or backward, or be able to control gravity but only for yourself and in increments of 10%?
Would you rather have the power to conjure any food you desire, but it's always slightly stale, or the power to summon any drink, but it's always lukewarm?
Would you rather be able to turn invisible, but only when you're holding your breath, or be able to become super strong, but only when you're extremely hungry?
Would you rather have the ability to understand all languages, but only when you're singing, or have the ability to speak all languages, but only through interpretive dance?
Would you rather be able to read minds, but only of people who are thinking about cheese, or be able to control small electronics, but only if they are yellow?
Would you rather have the power to make anyone fall asleep, but they wake up with no memory of the last hour, or have the power to make anyone extremely happy, but they are uncontrollably giggly for ten minutes?
Would you rather be able to breathe underwater, but only in a bathtub, or be able to fly, but only a foot off the ground?
Would you rather have the ability to communicate with trees, but they only tell you sad stories, or have the ability to communicate with rocks, but they only complain about being stepped on?
Would you rather be able to perfectly juggle anything, but only with your feet, or be able to tie any knot, but only with your teeth?
Would you rather have the power to create illusions, but they always backfire in a comical way, or have the power to influence emotions, but only to make people slightly annoyed?
Would you rather be able to summon a delicious meal for yourself at any time, but it always has one ingredient you can't stand, or be able to summon a perfect outfit for any occasion, but it's always one size too small?
Would you rather have the ability to change the color of anything you touch, but only to shades of beige, or have the ability to make anything levitate, but only an inch off the ground?
Would you rather be able to communicate with fungi, but they're all existentialists, or be able to communicate with insects, but they only offer unsolicited dating advice?
Would you rather have super speed, but you can only run backwards, or have super strength, but you can only use it to open jars?
Would you rather be able to see in the dark, but only when you're wearing sunglasses, or be able to hear incredibly well, but only when you're wearing earmuffs?
Would you rather have the ability to control the weather, but only within a 10-foot radius around you, or have the ability to talk to animals, but they only complain about your fashion choices?
Would you rather be able to teleport, but you always arrive with a mild rash, or be able to teleport, but you can only go to places you've already been that day?
Would you rather have the power to make people instantly forget what they were doing, but only if they were having fun, or have the power to make people remember trivial facts, but only if they are embarrassing?

Unusual Unpleasantries

Would you rather have a permanent taste of lukewarm milk in your mouth, or have a constant feeling of static electricity on your skin?
Would you rather have to wear itchy wool underwear every single day, or have every meal be slightly too spicy for your liking?
Would you rather have your fingernails grow an inch every hour, or have your toenails grow an inch every hour?
Would you rather have a constant, low hum in your ears, or have a constant feeling of a mild itch you can never quite reach?
Would you rather have to sleep on a bed of Legos every night, or have to walk barefoot on a path of hot coals for five minutes every morning?
Would you rather have all your food taste like cardboard, or have all your drinks taste like bitter coffee?
Would you rather have your sense of smell replaced with the smell of gym socks, or have your sense of taste replaced with the taste of disappointment?
Would you rather have to wear wet socks for the rest of your life, or have to wear a shirt that's always slightly damp?
Would you rather have a constant tickle in your throat that makes you want to cough, or a constant urge to sneeze that you can never quite fulfill?
Would you rather have your hair turn a different, embarrassing color every day, or have your teeth constantly feel fuzzy?
Would you rather have to live in a house where all the furniture is made of Jell-O, or a house where all the walls are covered in sticky notes?
Would you rather have to eat a spoonful of mayonnaise every hour, or a spoonful of mustard every hour?
Would you rather have your shadow constantly try to trip you, or have your reflection occasionally mock you?
Would you rather have to wear a hat that plays elevator music every time you move, or shoes that squawk like rubber chickens with every step?
Would you rather have your dreams be a constant loop of trying to find a parking spot, or a constant loop of trying to use a public restroom?
Would you rather have to speak in a squeaky voice for the rest of your life, or have to walk with a limp for the rest of your life?
Would you rather have your nose constantly drip a thick, sticky syrup, or have your ears constantly fill with sand?
Would you rather have to smell burnt popcorn for the rest of your life, or smell a skunk whenever you get nervous?
Would you rather have your voice sound like a chipmunk whenever you're angry, or sound like a grumpy old man whenever you're happy?
Would you rather have to eat everything with a fork, even soup, or have to eat everything with a ladle, even small snacks?

Baffling Behaviors

Would you rather have to greet everyone you meet with a dramatic bow, or have to say "Ta-da!" every time you finish a task?
Would you rather have to communicate solely through interpretive dance, or have to communicate solely through opera singing?
Would you rather have to wear a clown nose every day, or have to wear oversized novelty glasses every day?
Would you rather have to apologize profusely to inanimate objects you bump into, or have to thank them profusely?
Would you rather have to walk backwards everywhere you go, or have to hop on one foot everywhere you go?
Would you rather have to start every conversation with a random fact about potatoes, or end every conversation with a dramatic sigh?
Would you rather have to spontaneously burst into song every time you feel embarrassed, or have to do a silly dance every time you get excited?
Would you rather have to wear a cape that trails behind you everywhere, or a hat that jingles like a bell with every nod?
Would you rather have to narrate your own life out loud in the third person, or have to whisper all your secrets to your houseplants?
Would you rather have to give everyone you meet a compliment, even strangers, or have to ask everyone you meet a strange, personal question?
Would you rather have to pat everyone on the head like a dog, or ruff your hair like a cat?
Would you rather have to make a dramatic entrance every time you enter a room, or a dramatic exit every time you leave?
Would you rather have to speak in rhymes all the time, or have to speak in questions all the time?
Would you rather have to hum a jaunty tune whenever you're thinking, or whistle a dramatic score whenever you're walking?
Would you rather have to pretend to be a robot when you're feeling tired, or pretend to be a pirate when you're feeling adventurous?
Would you rather have to salute everyone you pass on the street, or curtsy to everyone you pass?
Would you rather have to end every sentence with a pun, or start every sentence with a sound effect?
Would you rather have to mime everything you say when you're in a quiet place, or sing everything you say when you're in a loud place?
Would you rather have to greet people by pretending to be a superhero, or say goodbye by pretending to be a secret agent?
Would you rather have to do a little jig every time you successfully complete a task, or perform a dramatic flourish every time you fail?

Absurd Abilities

Would you rather have the ability to perfectly parallel park any vehicle, but only if you're wearing roller skates, or have the ability to understand the stock market, but only if you're blindfolded?
Would you rather be able to talk to pigeons, but they only tell you secrets about their nesting habits, or be able to communicate with dust bunnies, but they only offer philosophical insights?
Would you rather have the power to control the temperature of your food, but only to slightly above room temperature, or the power to change the texture of your food, but only to slightly chewy?
Would you rather be able to predict the next song on the radio with 100% accuracy, but only if it's a song you dislike, or be able to guess the exact number of jellybeans in any jar, but only if you're not looking?
Would you rather have the ability to perfectly fold a fitted sheet on the first try, or the ability to always know the correct time without looking at a clock?
Would you rather have the power to make all your socks mysteriously disappear, or the power to make all your pens run out of ink at the most inconvenient moments?
Would you rather be able to communicate with furniture, but they're all incredibly judgmental, or communicate with clouds, but they only rain in polite drizzles?
Would you rather have the ability to instantly master any board game, but only if you're playing against a child, or the ability to perfectly guess the outcome of any coin flip, but only if it's a foreign currency?
Would you rather be able to control the speed of traffic lights, but only to make them stay red longer, or be able to influence the wifi signal, but only to make it slightly weaker?
Would you rather have the ability to change the flavor of your water, but only to slightly salty, or the ability to change the scent of your car, but only to mildew?
Would you rather be able to find a parking spot anywhere, but only if you're singing opera, or be able to untangle any knot, but only if you're wearing oven mitts?
Would you rather have the power to make your printer work perfectly, but only if you are humming a specific tune, or the power to make your toaster pop up perfectly golden brown, but only if you compliment it?
Would you rather be able to communicate with garden gnomes, but they only offer gardening tips that are wildly inaccurate, or communicate with garden slugs, but they only complain about their slimy trails?
Would you rather have the ability to perfectly skip any song you hear, but only if it's your favorite song, or the ability to rewind any conversation, but only to a point where it becomes awkward?
Would you rather be able to predict the winning lottery numbers, but they are always for a lottery that happened yesterday, or be able to teleport, but only to the nearest public restroom?
Would you rather have the power to make any digital device freeze, but only if it's working perfectly, or the power to make any analog device malfunction, but only if it's essential?
Would you rather be able to understand the language of socks, but they only talk about being lost, or understand the language of rubber bands, but they only complain about being stretched?
Would you rather have the ability to conjure a delicious sandwich, but it's always missing one key ingredient, or conjure a perfect cup of coffee, but it's always slightly too bitter?
Would you rather be able to control the flow of time, but only in very small, unnoticeable increments, or be able to control your own weight, but only by shifting it between different body parts?
Would you rather have the power to make your remote control work from any distance, but it only controls other people's devices, or the power to find lost items, but they are always items you don't want?

Slightly Sinister Scenarios

Would you rather have a ghostly figure that follows you everywhere and silently judges your fashion choices, or have a disembodied voice that whispers compliments to you at inconvenient times?
Would you rather have your dreams be nightmares where you're constantly trying to escape a room filled with sentient socks, or have your waking life be punctuated by the sound of phantom giggling?
Would you rather have a small, mischievous imp that rearranges your belongings when you're not looking, or a shadowy figure that occasionally appears in your peripheral vision, but never does anything threatening?
Would you rather have to wear a collar that barks whenever you tell a lie, or have to wear a hat that glows red whenever you have a bad thought?
Would you rather have your reflection in mirrors occasionally smile sinisterly at you, or have your shadow sometimes detach and dance on its own?
Would you rather have a book that constantly changes its ending every time you read it, or a diary that writes your deepest fears in glowing ink?
Would you rather have a personal soundtrack play dramatic music whenever you walk into a room, or have a recurring dream where you're being chased by very slow, but persistent, sentient dust bunnies?
Would you rather have a pet that looks innocent but secretly plots your mild inconvenience, or a friendly ghost that insists on helping you with chores, but always makes them worse?
Would you rather have your favorite childhood toy come to life, but it's incredibly creepy and only whispers your embarrassing childhood memories, or have all your inanimate objects whisper your secrets to each other at night?
Would you rather have a phantom itch that you can never quite scratch, or a phantom tickle that makes you want to sneeze but you can't?
Would you rather have your alarm clock wake you up with a bloodcurdling scream every morning, or have your phone make all your outgoing calls sound like they're coming from a cartoon villain?
Would you rather have a permanent, faint smell of damp earth about you, or a faint smell of something that might be rotting, but you can't quite place it?
Would you rather have your handwriting spontaneously change to a chaotic scribble whenever you're stressed, or have your voice crack at the most important moments?
Would you rather have a door appear in your wall that leads to an empty, dusty room you can never leave, or have a window that shows you glimpses of slightly unsettling alternate realities?
Would you rather have a familiar lullaby play faintly whenever you're alone, but it's slightly off-key, or have your favorite songs occasionally glitch and play backwards?
Would you rather have your shadow constantly try to trip you, or have your reflection occasionally give you a judgmental stare?
Would you rather have your dreams be filled with talking animals who are all plotting against you, or have your dreams be about trying to flee a never-ending maze?
Would you rather have a personal rain cloud that follows you and drips just enough to make your hair perpetually damp, or a personal fog that follows you and makes it hard for people to see your face clearly?
Would you rather have a phantom hand occasionally pat you on the shoulder, or a phantom whisper that sounds like your name, but no one is there?
Would you rather have to wear clothes that are always slightly too small, or clothes that are always slightly too big and ill-fitting?

Themed Tricky Choices

Would you rather be able to talk to plants, but they only complain about being watered, or talk to insects, but they only offer bad dating advice?
Would you rather have your entire house be soundproof, but you can never hear anything outside of it, or have your entire house have perfect acoustics, but every sound echoes infinitely?
Would you rather have to eat all your meals with oversized novelty cutlery, or have to drink all your beverages from tiny doll-sized cups?
Would you rather have your personal theme song be a kazoo rendition of a sad ballad, or have your footsteps sound like a squeaky rubber chicken?
Would you rather have the ability to fly, but only when you're singing loudly, or the ability to teleport, but only to the nearest bathroom?
Would you rather have your dreams be exclusively about trying to find a parking spot, or have your dreams be about being chased by a single, relentless banana peel?
Would you rather have your reflection in mirrors occasionally wink at you, or have your shadow occasionally try to steal your shoes?
Would you rather have to wear mismatched socks every day for the rest of your life, or have to wear gloves on your feet?
Would you rather have your pet understand everything you say, but only respond with bad dad jokes, or have your appliances talk to you, but only to complain about their jobs?
Would you rather have the power to make it rain, but only indoors, or the power to make it snow, but only in the desert?
Would you rather have your nose run constantly, but only with glitter, or have your ears clog up with popcorn kernels every morning?
Would you rather have to communicate solely through animal sounds, or solely through interpretive dance?
Would you rather have your internal monologue narrated by a very enthusiastic game show host, or have all your thoughts appear as subtitles on a tiny screen above your head?
Would you rather have a personal cloud that follows you and rains lightly whenever you're happy, or a personal sunshine that follows you and always feels cold even in summer?
Would you rather have to start every sentence with "Honestly," or end every sentence with "…probably"?
Would you rather have your hair always look like you just woke up, or have your clothes always feel slightly damp?
Would you rather have the ability to teleport, but you always arrive with a mild rash, or be able to teleport, but you can only go to places you've already been that day?
Would you rather have your urine smell like freshly baked bread, or have your sweat smell like your favorite perfume?
Would you rather have to eat a spoonful of honey every hour, or a spoonful of sriracha every hour?
Would you rather have your voice sound like a robot when you're tired, or sound like a squeaky toy when you're excited?

So, there you have it – a collection of Obscure Would You Rather Questions to twist your brain and tickle your funny bone. These aren't just random pairings; they're invitations to explore the absurd, ponder the improbable, and engage in hilarious debates. The next time you find yourself in a conversation rut, pull out some of these obscure dilemmas. You might be surprised by the laughter, the insights, and the sheer joy of choosing between two equally bewildering, but undeniably fun, options.