100 Extremely Worst would you rather questions to ask people

By: Kevin Grant

Ever spent hours debating the merits of pineapple on pizza or the ethics of socks with sandals? Prepare to have your mind BLOWN with 100 questions so outrageous, so hilariously horrifying, that choosing will feel like facing a dragon… while wearing socks with sandals.

Get ready to squirm, laugh, and ponder the deepest existential questions (like, would you rather have permanently sweaty hands or always smell like burnt toast?). This epic list will push your limits, reveal hidden truths about your friends, and leave you questioning everything you thought you knew about yourself.

So, gather your brave souls, grab your favorite decision-making beverage (we recommend a strong margarita for this one!), and prepare to enter the twisted wonderland of “Would You Rather” extremes! Buckle up, it’s gonna be a wild ride!


Most Worst would you rather questions

The following are some most worst would you rather questions:

1. Would you rather have the power to bring immense joy to others but never experience happiness yourself, or be constantly euphoric but unable to share that joy with anyone?

2. Would you rather live in a world where everyone can read your thoughts, or a world where you can hear everyone else’s thoughts but they are all negative about you?

3. Would you rather be condemned to relive your most embarrassing moment every day for a year or forget who you are every time you meet someone new?

4. Would you rather have the ability to know the exact moment of your death or the ability to know the moment of everyone else’s death?

5. Would you rather be forced to watch a 24-hour video of your most painful experiences or have others watch it with you?

6. Would you rather have the power to resurrect one person from the dead, but only if you sacrifice the life of another, or let both remain dead?

7. Would you rather live without the internet for the rest of your life or have your entire internet history accessible to anyone who searches for your name?

8. Would you rather always feel like you’re being watched, even when you’re alone, or constantly be haunted by the feeling that you’re being followed?

9. Would you rather know the answer to every question but never be able to share the knowledge, or be forever ignorant but able to freely communicate with others?

10. Would you rather be able to control time but never age or be immune to all diseases but age twice as fast?

11. Would you rather be cursed to speak in riddles that nobody can understand or have every conversation you engage in turn into an argument?

12. Would you rather have the ability to feel the physical pain of others or have them feel your pain?

13. Would you rather have to relive your worst day ever once a year or have every day be just slightly worse than the one before?

14. Would you rather have the power to bring world peace but sacrifice your own happiness, or live in constant conflict and misery but retain personal joy?

15. Would you rather be constantly surrounded by the sound of a baby crying or have the perpetual feeling of nails on a chalkboard whenever you hear laughter?

Useless Would you rather worst questions

The following are some useless would you rather worst questions:

1. Would you rather have a pet rock that whispers conspiracy theories or a cactus that judges your outfit choices?

2. Would you rather brush your teeth with toothpaste flavored like pickles or floss with cheese-flavored string cheese?

3. Would you rather wear a shirt covered in pictures of your least favorite food or pants with the pockets sewn shut?

4. Would you rather sing karaoke in front of your worst enemy or give a public lecture on a topic you know nothing about?

5. Would you rather eat a bowl of cereal with chopsticks or write a love letter with your feet?

6. Would you rather spend a day stuck in a room full of balloons or a room full of packing 


7. Would you rather speak only in movie titles for a week or only in song lyrics for a month?

8. Would you rather have hair that constantly smells like popcorn or teeth that permanently glow 

in the dark?

9. Would you rather wear socks with sandals or wear a winter coat in the summer?

10. Would you rather sleepwalk through your neighbor’s yard or talk in your sleep during a job interview?

11. Would you rather write a novel with your left hand or paint a masterpiece with your nose?

12. Would you rather sing the national anthem backwards or recite your grocery list in a Shakespearean accent?

13. Would you rather smell like pizza forever or only be able to eat bland, flavorless food?

14. Would you rather have a pet goldfish that can predict the weather or a pet snail that talks in puns?

15. Would you rather get your hair stuck in a revolving door or accidentally walk into a stranger’s shower?


The worst would you rather questions ever

The following are some of the worst would you rather questions:

1. Would you rather accidentally reply to a sensitive work email or call your boss by the wrong name during a presentation at the office?

2. Would you rather have your office chair make a loud, embarrassing noise every time you sit down or have your computer play a random meme at full volume during important meetings at work?

3. Would you rather wear mismatched shoes to an important meeting or have your coffee spill on your lap during a video conference at the office?

4. Would you rather have your browser history shared with your coworkers or accidentally send a text complaining about your job to your boss?

5. Would you rather have a persistent case of the hiccups during a crucial client call or realize you left your microphone on while using the restroom during a virtual meeting at work?

6. Would you rather have your most embarrassing college moment broadcasted on the campus news or be the subject of a viral meme that everyone in your college sees?

7. Would you rather accidentally send a love letter to your professor or have your search history exposed during a lecture in college?

8. Would you rather have your backpack explode in a crowded hallway, revealing your most personal items, or trip and fall in front of your crush during a campus tour in college?

9. Would you rather forget your lines during a class presentation or realize your pants are unzipped after a lecture in college?

10. Would you rather have your college nickname based on your most embarrassing moment or have it be a random embarrassing sound you make in college?

11. Would you rather spill food on yourself during the first date or accidentally call your date by your ex’s name?

12. Would you rather have your phone ring loudly during a romantic moment or accidentally send a text meant for a friend to your date?

13. Would you rather accidentally reveal too much about your past on a first date or realize you’ve been pronouncing your date’s name wrong the entire time?

14. Would you rather have your most embarrassing dating story shared on social media by your date or accidentally mention your ex’s name while professing your feelings on a date?

15. Would you rather have your date’s parents walk in on an intimate moment or mistakenly send a text meant for your date to your own parents on a date?

Nonsense would you rather questions worst edition

The following are some nonsense would you rather questions worst edition::

1. Would you rather have spaghetti for hair that grows one inch per day or sweat maple syrup whenever you get nervous?

2. Would you rather only be able to communicate through interpretive dance or have a pet rock that critiques your life choices?

3. Would you rather have a nose that honks like a clown horn whenever someone compliments you or ears that whistle like a teapot when you’re thinking hard?

4. Would you rather have a personal cloud that follows you around and rains glitter or have a talking pineapple as your financial advisor?

5. Would you rather only be able to travel by somersaulting or have a pocket-sized giraffe that insists on giving motivational speeches at inappropriate times?

6. Would you rather have a third eye on your forehead that sees into the future but only predicts trivial events or have a tail that spontaneously recites Shakespearean soliloquies?

7. Would you rather have an alarm clock that wakes you up with random animal noises or a toaster that dispenses inspirational quotes along with your toast?

8. Would you rather sneeze confetti every time you meet someone new or hiccup glitter whenever you hear the word “pizza”?

9. Would you rather have the ability to summon a flock of seagulls on command or be followed by a swarm of butterflies that critique your fashion choices?

10. Would you rather have fingers that change colors based on your emotions or toes that sing Broadway show tunes whenever you take a step?

11. Would you rather have the power to turn invisible but only when no one is looking or be able to fly but only during a lunar eclipse?

12. Would you rather have eyebrows that change shape and express your mood or a talking plant that gives unsolicited relationship advice?

13. Would you rather have a pet rock that can speak but only in puns or a sentient balloon that follows you around and insists on telling bad jokes?

14. Would you rather have a personal soundtrack that plays whenever you enter a room, or have the ability to summon a disco ball at any awkward moment?

15. Would you rather have a mirror that compliments your outfit sarcastically or shoes that refuse to let you walk in a straight line?


Worst nasty would you rather questions

The following are some worst nasty would you rather questions:

1. Would you rather share your most embarrassing thought with a total stranger or keep it to yourself forever?

2. Would you rather prefer intimate moments at night, in the morning, mid-afternoon, or just wait for the perfect moment?

3. Would you rather be seduced with words or through meaningful gestures?

4. Would you rather have a wild daydream at work or maintain a strictly professional mindset?

5. Would you rather have a harmonious relationship with your boss or excel professionally in a non-sexual manner?

6. Would you rather discreetly handle personal desires in public or wait until you’re in private?

7. Would you rather avoid public bathroom activities or handle them discreetly?

8. Would you rather think about the most random things or maintain focus while in a private moment?

9. Would you rather use traditional methods or explore unique ways to enhance personal experiences?

10. Would you rather remember a moment that made you feel alive or forget the first time you felt arousal?

11. Would you rather share your first intimate experience with someone close or keep it to yourself?

12. Would you rather vividly remember your first intimate moment or embrace the beauty of new experiences?

13. Would you rather know everyone’s name or keep personal connections meaningful?

14. Would you rather enjoy a short and sweet experience or savor a more extended, passionate encounter?

15. Would you rather share personal stories or keep daring adventures private?

Worst would you rather questions dirty edition

The following are some worst would you rather questions dirty edition:

1. Would you prefer receiving a candid message or a playful text?

2. Would you rather experiment with a new position or try out a new form of intimacy?

3. Do you lean towards watching content or reading romantic literature?

4. If given the choice, would you pick a romantic encounter with your favorite celebrity or an admired personality?

5. Would you rather experience a quick and satisfying moment or indulge in a more prolonged and passionate connection, even without reaching climax?

6. Do you feel more comfortable with subdued lighting or bright illumination during intimate moments?

7. When concluding a first date, do you prefer a warm connection or a more passionate farewell?

8. If your partner could only use either their hands or their mouth during foreplay, which would you choose?

9. Would you be more inclined to try pole dancing or lap dancing for fun?

10. Given the option, would you prioritize exceptional foreplay or an exceptional main event in the bedroom?

11. In the realm of physical affection, would you rather engage in mutual foot-related experiences or have your partner do so?

12. Would you prefer capturing moments through a visual recording or expressing them through written narratives?

13. If incorporating different sensations into foreplay, would you lean towards wax play or incorporating spanking?

14. In an imaginary scenario, would you rather lose the sense of touch or the sense of taste?

15. When it comes to intimate encounters, would you rather excel in the art of foreplay or in the act itself, but not both?


High fives all around, decision-making champions! You’ve faced dragons (metaphorical, hopefully!), wrestled with crazy situations, and (probably) still like each other (mostly).  Remember, there are no “wrong” answers (except maybe for the socks one… ew).

The real win is the laughter, the groans, and the hilarious (or horrifying) discoveries you made about yourselves. Now, go forth and unleash these mind-bending “Would You Rathers” on the world! Just, uh, don’t blame us if friendships break, brains melt, or everyone suddenly craves burnt toast.  We’re off to bleach our own brains after writing them. Catch you next time, brave souls!

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I am a relationship expert passionate about helping people forge deeper connections. I believe strong communication is the foundation of any relationship. Through open conversations, I guide individuals and couples in building trust and understanding. My goal is to equip you with the tools to navigate conflict, strengthen bonds, and cultivate fulfilling relationships.

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