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Deep Would You Rather Questions

Deep would you rather questions are a great way to get to know someone. It starts with a simple prompt, “Would you rather…” Followed by an A or B question. The other person picks one. And the winners are both of you because you got to know each other better.

P.S. I like this YouTube edition if you want a video version!

Deep would you rather question
Deep would you rather question

The best deep would you rather questions

—Deep would you rather questions

  • Would you rather prefer to live in infamy in the annals of history or perish in obscurity?
  • Would you rather choose to be the most well-rounded and adaptable person in the world or to be one of the world’s top specialists in a particular field?
  • Would you rather choose to Be intelligent or more muscular than average?
  • Would you rather want to have the title of the world’s richest person or the title of the world’s most intelligent person?
  • Would you rather eat something delicious but harmful or eat something that was both delicious and unhealthy for you?
  • Would you rather prefer have happened: that you inadvertently killed two adults or that you accidentally killed a child?
  • Would you rather want to adopt—a dog or a cat?
  • Would you rather want that all of your phone’s conversations leaked or all of its pictures?
  • Would you rather prefer asking a favor of your ex or a stranger?
  • Would you rather be three hours early or five minutes early?
  • Would you rather choose to be a monk or a priest?
  • Would you rather choose to lead—a cult or a religion?
  • Would you rather have the power to alter history or have access to the future?
  • Would you rather have the power to destroy your memories or those of others?
  • Would you rather prefer a partner who can read your mind or a partner who can read others’ minds?
  • Would you rather prefer to communicate with animals or be able to converse in all human languages? 
  • Would you rather spend the rest of your life speechless or blind?
  • Would you rather prefer a once-in-a-lifetime experience that only a select few people will ever have or a once-in-a-lifetime experience that many people have already had?
  • Would you rather prefer living a life where you can never forget anything or living where you can never recall anything?
  • Would you rather spend the remainder of your days in solitary confinement or a prison cell?
  • Would you rather prefer living in a nation where the government nearly always follows the law or in one where they have to pay attention to you?
  • Would you rather choose: a world free of sickness or one with fair wealth distribution?
  • Would you rather prefer—living to be 100 or 500 years old?
  • Would you rather choose never experiencing failure or ever being rejected?
  • Would you rather have your whole life’s events made into a film you can watch anytime you want to recall them or a book that anybody can read and interpret?
  • Would you rather choose the ability to teleport or the ability to reside in a place where you could quickly speak the language?
Deep would you rather question
Deep would you rather question

Deep questions about love and intimacy

—Deep would you rather questions about intimacy and love

  • Would you rather like to get a back or foot massage?
  • Would you rather like a hug or cuddle up on the couch?
  • Would you rather choose between a porch swing and a Ferris wheel?
  • Would you rather choose late-night phone calls or fun texting all day?
  • Would you rather choose a horoscope compatibility chart or a psychic reading?
  • Would you rather like to get a flirting glance during dinner or play footsie?
  • Would you rather want to gaze at one another or the stars?
  • Would you rather eat chocolate-covered strawberries or Godiva chocolates?
  • Would you rather slow dance or duet singing?
  • Would you rather prefer to sit by a campfire or hold hands at the movies?
  • Would you rather want to get jewelry or a new room for your anniversary?
  • Would you rather prefer to spend the holidays with family or alone?
  • Would you rather keep your hobbies separate, or do you prefer to share them?
  • Would you rather want to sing along to your favorite song as a group or listen to a recording?
  • Would you rather hurt your partner’s feelings by telling the truth out loud or by telling a white lie?
  • Would you rather forgive your ex or harbor resentment?
  • Would you rather attempt something novel with your spouse or stick with the tried-and-true?
  • Would you rather prefer a spontaneous vacation or careful planning?
  • Would you rather prefer a condom with bright colors or one with odd patterns?
  • Would you rather want to have sex in your childhood bedroom or your childhood basement?
  • Would you rather like to suck from a person’s body whipped cream or ice cream?
  • Would you rather like to receive as a romantic gift: lingerie or dirty toys?
  • Would you rather prefer to wear underwear every day or never again?
  • Would you rather like to kiss—your ex or a mortal enemy?
  • Would you rather want to marry a pastry chef or a restaurant chef?
  • Would you rather want to meet your current crush or your old flame?
  • Would you rather kiss your roommate or a total stranger?
  • Would you rather spend $5 on a subpar sex toy or $100 on one of the best?
Deep would you rather question
Deep would you rather question

Deep questions for a crush

—Deep would you rather questions for a crush

  • Would you rather prefer a fastball to the crotch or someone giving your dick a paper cut perpendicular to the hole?
  • Would you rather be in the center of your parents, your brother, your dog, or a human centipede?
  • Would you rather like to suck a used condom or a used tampon you discovered on the street?
  • Would you rather prefer to participate once in their sexual activity or have to see it every night for the remainder of your life?
  • Would you rather choose between being alone your entire life or dating a hot killer?
  • Would you rather want to eat—a live spider or a dead rat?
  • Would you rather find more seductive, blood or insects?
  • Would you rather prefer to pass away without experiencing any psychological harm or be abducted for six months?
  • Would you rather want to find in your backyard: a dead body or simply the guts?
  • Would you rather prefer to find in your kitchen: a human skull or a human hand?
  • Would you rather like to lose first: your hands or your genitalia?
  • Would you rather prefer being stuck in a burning building with no way out, or drowning in a bathtub?
  • Would you rather prefer to be eaten alive, a wolf or a bear?
  • Would you rather prefer being tethered to a radiator in an empty room or having an IV in a spooky hospital?
  • Would you rather like to encounter Norman Bates in a hotel or Freddy Krueger in your dreams?
  • Would you rather drive away or run over a body to see who you hit?
  • Would you rather prefer: odd shadows on your wall or unusual noises in the middle of the night?
  • Would you rather want to be trapped in the woods with—Hannibal Lecter or Slenderman?
  • Would you rather prefer to stay in a haunted hotel or a hospital for the insane?
  • Would you rather light it on fire or soak it in acid?
  • Would you rather see ghosts wherever you go or go blind?
  • Would you rather prefer getting away with murder or being found guilty of a crime you didn’t commit?
  • Would you rather see their spirits or hear their voices? 
  • Would you rather prefer a straightforward connection that fails or a long-distance relationship that succeeds?
  • Would you rather solve a Rubik’s cube in 10 seconds or ride a unicycle across a tightrope?
  • Would you rather prefer to be healthy but look awful, or be unwell yet look fantastic?
  • Would you rather prefer living in your ideal house in a mediocre neighborhood or your ideal home in a mediocre neighborhood? 
  • Would you rather prefer: a stress-free life or an unrestricted life?
Deep would you rather question
Deep would you rather question

Freaky questions

  • Would you rather gain 200 pounds for the rest of your life or lose your sex organs forever?
  • Would you rather not have sex with your cousin but have everyone believe you did, or vice versa?
  • Would you rather prefer the nicest house in a run-down neighborhood or the worst house in a posh one?
  • Would you rather prefer five penises or none at all?
  • Would you rather lack arms or legs?
  • Would you rather choose no fingers or eyes?
  • Would you rather prefer to relieve yourself in secret every day for the rest of your life or to relieve yourself in public once a year?
  • Would you rather choose once having sex with your brother or sister or remaining a virgin forever?
  • Would you rather prefer—knives or penises for fingers?
  • Would you rather want to pass away within the next five minutes or live forever?
  • Would you rather marry Charlie Sheen or Paris Hilton?
  • Would you rather prefer: being extremely wealthy and required to work for Justin Bieber or being extremely poor and able to work for anybody you want?
  • Would you rather live knowing that everyone would know that you opted not to save the lives of 10,000 strangers? Or would you rather die rescuing 10,000 strangers from death, knowing that no one would ever know it was you?
  • Would you rather prefer: that everyone thinks your life is terrible, but in reality, it’s great? Or that everyone thinks your life is awful, but in reality, it’s great? 
  • Would you rather like to have: a time machine that only travels in the past or a time machine that only travels in the future?
  • Would you rather choose: endless love or endless wealth?
  • Would you rather choose: unrestricted power or unrestricted respect?
  • Would you rather spend your life the way it is now or get everything you’ve ever desired but pass away in a year?
  • Would you rather choose: a gorgeous fool or an ugly genius?
  • Would you rather never be permitted to wear clothing but be able to keep your thoughts to yourself? Or would you prefer to have your ideas broadcast so that everyone can constantly know what you are thinking as you are thinking it?
  • Would you rather have mild acne that affects your face or terrible acne that only affects portions of your body hidden by clothing?
Deep would you rather question
Deep would you rather question

Deep questions for couples

—Deep would you rather questions for couples

  • Would you rather be with an athletic adventurer or a bookish nerd?
  • Would you rather prefer living in a large metropolis or a rural town?
  • Would you rather prefer using your partner’s toothbrush or wearing their underwear?
  • Would you rather prefer for your significant other: chronic body odor or persistent poor breath?
  • Would you rather pass out during your wedding or a business presentation?
  • Would you rather prefer not to have to cook for your lover every night of the week or eat takeaway every night?
  • Would you rather prefer: having a tattoo of your ex or having a tattoo of your partner’s ex?
  • Would you rather be perpetually occupied or perpetually bored?
  • Would you rather be incredibly clever or incredibly funny?
  • Would you rather live in pajamas or a suit jacket for the rest of your life?
  • Would you rather skip: taking a shower or brushing your teeth for a month?
  • Would you rather be opulently wealthy or well known around the world?
  • Would you rather like to have: the best sense of humor or the best looks in the room?
  • Would you rather prefer to have more of in your home: rats or cockroaches?
  • Would you rather have a year without the internet or texting?
  • Would you rather choose to visit: an exciting, vibrant metropolis or a stunning alpine landscape?
  • Would you rather prefer someone who speaks with a lisp or a loud, piercing voice?
  • Would you rather date: a classical pianist or a comedian?
  • Would you rather prefer to kiss someone with horrible breath or nasty poop?
  • Would you rather prefer one leg or one arm?
  • Would you rather flash your former employer or moon a stranger?
  • Would you rather prefer writing your autobiography or letting someone else make a movie about your life?
  • Would you rather like to visit: the past or the future in 100 years?
  • Would you rather choose to give up for good: coffee or alcohol?
  • Would you rather deal with uncontrollable silent gas or obnoxious sneezing for the rest of your days?
  • Would you rather be surrounded by wild creatures and poisonous plants in a jungle or left stranded in a desert without water or a sense of direction?
Deep would you rather question
Deep would you rather question

Philosophical and deep would you rather questions

  • Would you rather battle one bull-sized ant or 1,000 ant-sized bulls?
  • Would you rather prefer: a hamster the size of a dog or a dog the size of a hamster?
  • Would you rather prefer: sweat mayonnaise or spaghetti for your hair?
  • Would you rather live forever with spinach in your teeth or an eyelash in your eye?
  • Would you rather prefer: laughing whenever someone tears or speaking in a British accent at all times?
  • Would you rather prefer: a tattoo on your face in the design of your choice or one in a covert location of someone else’s choosing?
  • Would you rather choose: breathing like Darth Vader or speaking like Yoda?
  • Would you rather prefer: the need to urinate after every inquiry you ask or the impulse to sneeze after every hello?
  • Would you rather prefer to wear—two size too big shoes or one size too tiny jeans?
  • Would you rather prefer: mistakenly liking an old Instagram photo of your ex or sending an inappropriate text to a family member?
  • Would you rather want to have public your Spotify listening history or your Netflix viewing history?
  • If you could only use emojis or slang phrases to communicate, which would you choose?
  • Would you rather choose: to eat solely McDonald’s at every meal or have to search for everything you eat?
  • Would you rather like to join: a daily book club or a fight club that only meets once a month?
  • Would you rather prefer never being able to speak again or constantly say what you’re thinking?
  • Would you rather prefer: being compelled to sing along with every song or being compelled to dance along with every song?
  • Would you rather choose: becoming a Death Eater or living a powerless life in the Harry Potter universe?
  • Would you rather prefer: to run into your famous crush right out of bed or to skip deodorant the day you meet them?
  • Would you rather prefer: that your pet can communicate with you but is unable to comprehend what you are saying? Or that your pet can hear every word you say but is unable to communicate?
  • Would you rather want to perform your favorite song alone in front of a large audience or simply with the original performer?
  • Would you rather glow bright red when someone upsets you or brilliant pink when you’re attracted to them?
Deep would you rather question
Deep would you rather question

Popular questions

—Popular deep would you rather questions

  • Would you rather marry your best friend or neighbor?
  • Would you rather spend all your life happy and broke or unhappy and rich?
  • Would you rather have all the happiness in the world or all the money?
  • Would you rather be in your dream job and broke or a bad job and rich?
  • Would you rather be the smartest person or the most attractive person?
  • Would you rather have only enough money to survive and be happy or be rich and not be as happy?
  • Would you rather eat meat or eat vegetables?
  • Would you rather have an intelligent life or a naive life?
  • Would you rather meet a celebrity in real life or a famous author?
  • Would you rather be a normal person in a weird world or a weird person in a normal world?
  • Would you rather have a one-night stand or a long-term relationship?
  • Would you rather have a photographic memory or super-smelling abilities?
  • Would you rather know the uncomfortable truth or get a white lie?
Deep would you rather question
Deep would you rather question

More fun games to play

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Fact checked:
Board reviewed by Marianne Tomlinson, LCSW (Couples and Family Therapy). Content is rigorously reviewed by a team of qualified and experienced fact checkers. Learn more.

About the author

Ryan Sanderson (LCSW) Ryan is a game and relationship enthusiast who enjoys all things quizzes, games, fun, love, relationships, and family. He's a licensed social worker and helps families, couples, and children in need. He's spoken about love and relationships on Salon.com, Forbes, and Mirror, to name a few.

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