Have you ever played a Would You Rather game? This is a great way to bond and connect.

Would You Rather can be a fun option if you’re looking for a conversation game to add to a game night with friends.

To play, have one person ask a would you rather question, and everyone else calls out their answers. Continue the game by having someone else ask a new would you rather question. 

Use this list of 245 Would You Rather questions to get started. 

50 Best Would You Rather Questions

  1. Would you rather be able to breathe underwater or fly? 

This question hits on a classic superpower standoff that is surprisingly divisive. 

  1. Would you rather only be able to eat sweet or savory food? 

You know, granting that they both affected your health in the same way. 

  1. Would you rather never be able to read another book or never watch another movie? 

Both are essential forms of art and communication. Which one would you pick? 

  1. Would you rather meet your great-great-grandparents or your great-great-grandchildren? 

The past you came from or the future you influenced—either one would be enjoyable. 

  1. Would you rather be a fantastic storyteller, inspired by embarrassing moments, or never do anything embarrassing but not have funny stories? 

Do you care more about life being “for the plot,” or do embarrassing moments stress you out so much you’d do anything never to have another one?

  1. Would you rather have to say every thought out loud or never be able to speak again? 

Despite your best efforts, you probably have a few ridiculous thoughts from time to time. How much do you care if people know what they are?

  1. If you had to choose, would you rather every shirt you put on be slightly itchy or only be able to use single-ply toilet paper? 

Unfortunately, either option would make life quite tedious.

  1. Would you rather every scoop of ice cream you ever eat be too melted or every brownie you ever eat be a corner piece? 

For those who like corner pieces of brownie, this is a pretty easy decision. 

  1. Would you rather break the world record for the fastest marathon but have to run everywhere you go instead of walking, or be considered the best chef but have to cook something intricate and time intensive every time you make a meal? 
  1. Would you rather live in a tree house or a tiny home by the beach? 

A spin on the classic ocean or forest question, but add the part where you’d have to be OK with living there! 

  1. Would you rather never be able to send another text and have all personal communication as a phone call or have a video zoom call every day? 

Talk about phone anxiety! 

  1. Would you rather be mildly allergic to dust or very allergic to pollen? 

A mild allergy all year round or a bigger allergy that flares up during the spring? 

  1. Would you rather have the power of teleportation or the ability of telekinesis? 

Getting anywhere in the blink of an eye would be amazing, but it would also be pretty awesome not to get up to turn off the lights. 

  1. Would you rather have to watch only horror movies or only rom-com for the next year? 

What do you look for when watching a movie—something lighthearted and sweet or more intense and adrenaline-raising? 

  1. Would you rather be exceptionally good at a niche sport that very few people know about or be OK at every sport you try? 

The internal struggle is between wanting to be a Jack of all trades and being “the best” at something. 

  1. Would you rather be a world-class bassoonist or an Olympic-level curler? 

Both are incredibly prestigious and impressive. 

  1. Would you rather live in perpetual winter and always be a little too cold or endless summer and always too warm? 

Unfortunately, neither is comfortable. 

  1. Would you rather dive from the 10m diving board or go scuba diving in caves? 

Which one scares you more—heights or depths? 

  1. Would you rather every movie was a musical or every store had a soundtrack? 

Horror movies would probably be less scary if everyone sang and danced together! 

  1. Would you rather date someone super into fitness or artistic?

Plenty of people are artistic and athletic, but it’s interesting to think about what you’d do if you had to choose just one or the other. 

  1. Would you rather date someone you would describe as “fun” or “reliable”?

These two traits are not exclusive! How you describe your partner can often say more about you than them. 

  1. Would you rather be able to speak to animals or make plants grow? 

The choice between flora and fauna—both incredible options! 

  1. Would you rather have to fight one horse-sized duck or 50 duck-sized horses? 

Who knows what challenges you might face in life?

  1. Would you rather have one-inch nails or wear a stiletto every work day? 

People who can cook meals with long nails or run errands in stilettos are superhuman. 

  1. Would you rather wear a sweat suit or be dressed to the nines daily? 

Some people love feeling comfy and casual while others love feeling fancy—which one are you? 

  1. Would you rather have an elephant’s trunk attached to your face or a neck as long as a giraffe? 

The elephant trunk would let you give people more hugs.

  1. Would you rather be allergic to gluten or dairy? 

Unfortunately, many people don’t get the choice and just get stuck with one (or both) of these allergies. 

  1. Would you rather have to fight Cerberus or Medusa? 

Neither of these options is excellent, with one being a three-headed dog that guards the underworld, while the other one’s a monster who turns people to stone when they look directly at her. 

  1. Would you rather sleep with socks on or wear socks and sandals? 

For some reason, socks in these two settings seem relatively polarizing. It’s interesting to learn who strongly feels about when socks should be worn and when they shouldn’t. 

  1. Would you rather hold a political office or have a friend of your choosing serve as president?

Are your friends the type of people you think would be able to lead a country well? 

  1. Would you rather have an unlimited supply of Chick-fil-A or Taco Bell?

Let the fast food wars commence! 

  1. If you had to, would you rather go back in time and fight in the Colosseum or the trenches of WWI? 

Both spaces are tragedy-filled, but which era and circumstances would you be more willing to navigate? 

  1. Would you rather travel with your significant other or best friends?

You could probably choose both, but if you had to choose…

  1. Would you rather only wear boots or flip-flops, regardless of the weather? 

If you choose socks, you may have to embrace wearing socks with flip-flops. 

  1. Would you rather be able to grow an awesome mustache or an awe-inspiring beard? 

If you choose the mustache, please get one of these mini hair dryers. 

  1. Would you rather go skydiving or bungee jumping? 

A great question for thrill-seeking friend groups. 

  1. Would you rather only drink coffee and no other beverages (except for water) or never be able to drink coffee again?

Learn just how devoted your friends are to coffee. 

  1. Would you rather have a window seat on the airplane or an aisle seat?

Getting up to stretch your legs is nice, but is it better than having a window view? 

  1. Would you rather retire early and be able to pour time into a humanitarian aid project or continue working until retirement age and change the company culture of your workplace? 

Either one is a fantastic legacy to leave behind! 

  1. Would you rather play on a team where you were close friends with everyone but lost roughly half your games or play on a section where you didn’t enjoy the people but consistently won?

This question can help you figure out who in your friend group plays sports to hang out with people and who wants to win. 

  1. Would you rather have a relationship like Jim and Pam from The Office or Nick and Jess from New Girl

You can’t go wrong with this one. They’re both pretty iconic power couples. 

  1. Would you rather reread a familiar comfort book or read something you’ve never read before? 

The constant struggle between something that feels comfortable and familiar and something exciting and new. 

  1. Would you rather have your favorite home-cooked meal or go to your favorite restaurant?

Some people love going out while others enjoy cooking something nice themselves—ask your friends, so you know who to invite over the next time you want to cook an elaborate dinner with someone. 

  1. Would you rather have the time to read 100 books every year or make 20 new friends? 

As with many other questions in this list, this comes down to helping one recognize how they spend their time. Is it going to places and meeting new people or learning new and exciting information while reading? 

  1. Would you rather invite someone you just met to be your +1 to a wedding or go solo?

Which one would you find more intimidating? Going solo to a wedding or going with someone you’ve never met before? 

  1. Would you rather have to yell, “I scream, you scream, we all scream for ice cream!” every time you eat anything or cry, “It’s raining, it’s pouring, the old man is snoring!” Every time you step outside of your house or car. 
  1. Would you rather do a Bachelor‘s marathon or an Amazing Race marathon? 

Either could be fun with good company and great snacks. 

  1. Would you rather your cat suddenly have human teeth or your dog starts speaking Italian? 

Either would feel like a bizarre world to wake up to. 

  1. Would you rather play a game of Monopoly or Settlers of Catan? 

Both games take a good couple of hours to play, so which would you rather? 

  1. Would you rather go ziplining through the amazon forest or ride a camel around the pyramids? 

Both would include beautiful sights and amazing animals.

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Funny Would You Rather Questions

Embrace the silly side of would you rather and ask some ridiculous questions! You can get creative and put your spin on any of these. 

  1. Would you rather have to skip everywhere instead of walking or singing instead of being able to speak? 
  2. Would you rather dress super formally every day or always be informally dressed? 
  3. Would you rather be able to bring inanimate objects to life or talk with animals? 
  4. Would you rather have to sing to every song you hear or dance any time you hear music? 
  5. Would you rather greet everyone with a high-five or call everyone you know (including your boss) “buddy”? 
  6. Would you rather participate in a 200-person food fight or a 5-day-long water balloon fight?
  7. Would you rather have everything you do appear on your body as a tattoo for 24 hours or have your skin color change based on your emotions? 
  8. Would you rather everyone listen to their music without headphones or chew loudly? 
  9. Would you rather your only form of transportation, besides walking, be a set of rollerblades or a unicycle? 
  10. Would you rather have the head of a unicorn and the body of a fish or the head of a fish and the body of a unicorn? 
  11. Would you rather your grilled cheese always be perfectly stringy or your soda never go flat? 
  12. Would you rather hear “There’s a snake in your boot” from Toy Story every time you put on your shoes or hear the theme song from Up every time you walk out your front door? 
  13. Would you rather have to climb in through the window or shower with your clothes on? 
  14. Would you rather vomit every time you see a clown or fart every time you eat garlic? 

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What one eats is a big part of their day. Learn more about your friend’s preferences and habits by asking a handful of food-related questions. 

  1. Would you rather eat a teaspoon of wasabi or a tablespoon of cinnamon? 
  2. Would you rather dinner guests praise your meal or your home decor? 
  3. Would you rather eat fruit at every meal or drink green juice every morning? 
  4. Would you rather take a pre-workout before going to sleep or go the entire day without caffeine? 
  5. Would you rather grow all your produce or harvest your honey? 
  6. Would you rather eat shark or bear meat? 
  7. Would you rather give up sweets or savory snacks? 
  8. Would you rather have a square of chocolate or popcorn every night? 
  1. Would you rather cook dinner for date night or have your partner cook for you? 
  2. Would you rather go to a brewery or a coffee roaster? 
  3. Would you rather hire a personal chef or a personal maid? 
  4. Would you rather have a birthday cake or birthday cupcakes? 
  5. Would you rather snack all day long but not have big meals, or only eat meals with no snacks? 
  6. Would you rather have someone help you cook, but they do things just a little differently than you’re used to, or someone help you clean, but they clean items up into different places than you are accustomed to?
  7. Would you rather have Pad Thai or pho?
  8. Would you rather eat pineapple on your pizza or dip your french fries in ice cream? 
  9. Would you rather never eat your favorite food again or be able to eat anything besides your favorite food? 
  10. Would you rather take a great photo of your restaurant meal or eat your food as soon as it arrives? 
  11. Would you rather share a meal with Jackie Chan or The Rock? 
  12. Would you rather have olives with every meal or vegemite for lunch once a week? 
  13. Would you rather cook using a cookbook or make up the recipe as you go? 
  14. Would you rather cook your favorite holiday food and enjoy it with 30 guests or share the meal with your close family and then enjoy leftovers for longer? 
  15. Would you rather have French baguettes or Italian pizza? 
  16. Would you rather travel back in time and share a meal with your favorite historical figure or share a meal with your favorite current celebrity? 
  17. Would you rather drink hot coffee that has cooled down to room temperature or iced coffee that was warmed up to room temperature? 
  18. Would you rather a first date happen over coffee or a meal? 
  19. Would you rather find the perfect cookbook in the thrift store or the ideal set of plates while antiquing? 
  20. Would you rather always have fresh berries in your refrigerator or always have warm cookies and milk? 
  21. Would you rather do the cooking or the cleaning? 
  22. Would you rather bake or cook? 
  23. Would you rather order a cocktail or a glass of wine with dinner? 
  24. Would you rather have pickles on your sandwich or blue cheese on your salad? 
  25. Would you rather have brunch out with friends or a night out with friends? 

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Adventure and Travel Would You Rather Questions

Before traveling with someone, it can be helpful to ensure you’re on the same page about your priorities. Tensions can rise if you get on the road and realize that you have different expectations of using your time while traveling. 

Use a few of these questions to see if you’re compatible travel buddies, or agree ahead of time on how you will compromise in the areas you differ. 

  1. If you were on a month-long trip, would you rather visit many different countries for only a few days each or spend the entire month in one place and get to know that country more in-depth? 
  2. Would you rather travel with friends to a location you aren’t as excited about or travel solo, going where you want but not sharing those experiences with anyone? 
  3. Would you rather go for a week-long hike in the Alps or spend a week in a resort in Cabo? 
  4. Would you rather swim with sharks or run into a bear while hiking? 
  5. Would you rather travel light or have everything you might need with you but have to lug it around? 
  6. Would you rather go to New York or Los Angeles? 
  7. Would you rather spend your travel budget on good food or museum tickets? 
  8. Would you rather travel somewhere you’ve been before and loved or somewhere you’ve never been? 
  9. Would you rather have a chill vacation or a high-intensity vacation? 
  10. Would you rather go skiing or snowboarding? 
  11. Would you rather find the perfect airplane book or travel outfit—warm but not too hot, comfortable, and functional? 
  12. Would you rather get free access to all the museums in the city you’re visiting or meet the most amazing locals willing to share their restaurant and coffee shop tips? 
  13. Would you rather take home a fantastic unique souvenir from the place you visited or capture the most amazing photos? 
  14. Would you rather visit Singapore or Hong Kong?
  15. Would you rather see the Pope while visiting the Vatican or the Dalai Lama while visiting Tibet? 
  16. Would you rather listen to music or podcasts while on a road trip? 
  17. Would you rather take a train or a bus while traveling? 
  18. Would you rather curate the perfect playlist for your travels or find the ideal book to read? 
  19. Would you rather go on a cruise and have the stress of planning a trip taken off your plate but have to follow someone else’s itinerary or explore on your own? 
  20. Would you rather try an unfamiliar local food or have something familiar that the locals don’t typically eat? 
  21. Would you rather be able to understand any language you hear without studying it or instinctively know directions for everywhere you go without looking at a map? 
  22. Would you rather go on a safari and see lots of amazing animals or go on a helicopter ride over beautiful nature? 
  23. Would you rather go camping in the woods or sleep in a hammock on the beach? 
  24. Would you rather look up and see a shark while surfing or wake up to 10 scorpions inside your tent while camping? 
  25. Would you rather go on a long road trip in the summertime with no AC or winter with no heating? 
  26. Would you rather get the most Instagram-worthy photos while traveling but stay on the beaten track or find the coolest hidden gems but not be able to take any pictures? 
  27. If you were stranded on a desert island, would you rather have the tools to build a raft and leave but have a limited food supply, or have endless food and clean water but have to wait in hopes that someone saw and rescued you? 

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The art world can be filled with dreamers and thinkers. Don’t be surprised if you ask one of your artistic friends a question, and they go on a tangent explaining their thought process or suggesting a third option. 

  1. Would you rather meet your favorite book character in real-life or wake up inside the world of your favorite book? 
  2. Would you rather only be able to listen to a single musical artist for the rest of your life or never be able to listen to your favorite artist again? 
  3. Would you rather go on tour as a musician or have an adamant literary critic compliment a poem or short story you wrote? 
  4. Would you rather wake up with the ability to play the saxophone at a world-class level or paint unique oil paintings? 
  5. Would you rather be able to make the perfect playlist for any occasion or always be able to recommend a book your friends would love? 
  6. Would you rather speak only in rhymes or have to do a beautiful pirouette every time you walk in or out of your front door? 
  7. Would you rather have to fight off a zombie with your favorite movie character or have to run away from a 10-foot spider with your favorite book character? 
  8. Would you rather your favorite musician release new music every day but never go on tour or have front row tickets to every concert on their tour, but they only drop a new album once every five years? 
  9. Would you rather wake up with the ability to sing beautifully, but anyone who hears you falls into a trance for 30 minutes, or be able to tell incredible stories that come to life? Still, there always has to be a villain in the story they create as well. 
  10. Would you rather play the piano or the violin? 
  11. Would you rather put on a 60-minute solo concert that everyone you know attends or put on a performance art piece, seen by thousands, in a museum? 
  12. Would you rather be able to see music or smell a painting visually? 

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Would You Rather Questions to Ask Adults

  1. If you had to choose, would you rather have the career of your dreams or the family you’ve always wanted? 
  1. Would you rather work a job you love that pays a modest salary or a job you’re just OK with that pays twice as much? 
  2. Would you rather go back in 1,000 years or forward in 1,000 years? 
  3. Would you rather your firstborn child be named by a random name generator or a group of your college friends? 
  4. Would you rather have all your closest friends come to your wedding and have a fantastic party or have them all visit you one by one over the following year and be able to spend more quality time with each one individually? 
  5. Would you rather set your best friend up with the partner of their dreams or always have them date someone new who is exciting and you enjoy meeting? 
  6. Would you rather always know what to wear to events but have a hard time talking with strangers or always know how to strike up an interesting conversation but be underdressed? 
  7. Would you rather only be able to only get your news from one media outlet that tends to be more polarized or only know the news events happening on one continent? 
  8. Would you rather have an at-home spa night with snacks and face masks or get a professional massage? 
  9. Would you rather get a glimpse of the future or forget something from your past? 
  10. Would you rather never have to pay taxes again (without breaking the law) or have an extra month of paid vacation time? 

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Would You Rather Questions for Kids

Asking kids in your life would rather questions can lead to some fun conversations and help you get an insight into what they are thinking. Questions like these where they can choose between two options can make it easier for young children to engage in the conversation as they have a limited number of options. 

  1. Would you rather live in forever winter or forever summer? 
  2. Would you rather be able to talk with animals or hear people’s thoughts? 
  3. Would you rather be a professional athlete or a professional actor or actress? 
  4. Would you rather play tag or hide-and-go-seek? 
  5. Would you rather have ice cream or pizza every day?
  6. Would you rather be able to run as fast as a jaguar or jump as high as a kangaroo? 
  7. Would you rather play basketball or guitar? 
  8. Would you rather live next door to your best friend or on a playground? 
  9. Would you rather have a little sister or a little brother? 
  10. Would you rather aliens invade the Earth or robots take over? 
  11. Would you rather go to Disneyland for one day or a beach resort for a week? 
  12. Would you rather find a quarter on the ground every time you go outside or get a dollar every time you see a rainbow?
  13. Would you rather be able to do a perfect cartwheel or sing a song perfectly?  
  14. Would you rather meet the president of the United States or the Queen of England? 
  1. Would you rather wake up and realize you were a lion or a penguin? 
  2. If you had to pick one type of sandwich for an entire year, would you rather only eat peanut butter and jelly sandwiches for lunch or ham and cheese sandwiches? 
  3. Would you rather have an ice cream cone for dessert but have to go to bed early or not have any ice cream but be able to stay up as late as you want? 
  4. Would you rather have your friends sleep over and stay up super late playing games or wake up early to go on a big adventure? 
  5. Would you rather school be four long days or six short days every week? 
  6. Would you rather spend a snow day sledding or building a snowman? 
  7. Would you rather speak to animals or know every language? 
  8. Would you rather have your favorite snack or play with your favorite toy? 

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Would You Rather Questions to Ask Your Friends

  1. Would you rather get stuck at the top of a Ferris wheel for an hour or have a flock of pigeons surround you at a train station for 20 minutes?
  2. Would you rather talk with your best friend weekly for an hour on the phone or see them once a year for a weekend? 
  3. Would you rather only be able to read books by your favorite author or only be able to watch movies from your favorite director for the next ten years? 
  4. Would you rather go back to the day you met your friend and relive that moment with all your recent memories of your friendship or get a five-minute glimpse of what your friendship will look like in 20 years? 
  5. Would you rather it start raining every time you step outside or have the clouds come out whenever you try to look at the stars? 
  6. Would you rather spend a weekend away together or call one another every day for a 15-minute check-in? 

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Would you Rather Questions for Athletes

The next time you want to start a conversation with someone wearing a sports jersey, try out one of these would you rather questions. 

  1. Would you rather your favorite team win every game, but you would know the game’s outcome ahead of time, making it less exciting, or have them win some games and lose others without knowing what would happen, making the matches more exciting? 
  2. Would you rather play pickleball or spikeball? 
  3. Would you rather play rugby or ultimate frisbee? 
  4. Would you rather be a professional hockey player or a professional speed skater? 
  5. Would you rather play soccer or baseball?
  6. Would you rather be a coach or a referee? 
  7. Would you rather coach minor league baseball or a soccer team of five-year-olds? 
  8. Would you rather go to the gym or go for a run? 
  9. Would you rather trail run or train springs? 
  10. Would you rather never get another sports injury again but only be able to play for three more years or play for ten years but have the possibility of painful injuries? 
  11. Would you rather do cardio or heavy lifting at the gym? 
  12. Would you rather have a personal trainer or plan your workout regimen? 
  13. Would you rather date someone who loves training in the gym or living an active, outdoor lifestyle? 
  14. Would you rather spend the day watching reruns of some of the most incredible soccer games ever played or attending a live match? 
  15. Would you rather watch an F1 race or a basketball game? 
  16. Would you rather be an incredible team player known for helping others on their team shine and score points or be a solo player? 
  17. Would you rather drink a protein shake before your morning workout or on an empty stomach? 
  18. Would you rather try the Keto diet for one month or do Paleo?
  19. Would you rather eat a rigorous diet and never have fast food or follow a strict workout plan and wake up two hours before work every day to fit in your workout?
  20. Would you rather watch the Super Bowl at home with all your friends and favorite snacks or go by yourself to the game and experience the atmosphere of being there? 
  21. Would you rather spend the day surfing or snowboarding? 
  22. Would you rather surf the North Shore of Hawaii or Bells Beach? 
  23. Would you rather get the instantaneous ability to skate a half-pipe or do an elite gymnastics routine? 
  24. Would you rather have a distance runner’s endurance or a swimmer’s shoulder strength? 
  25. Would you rather run out of electrolyte water while doing a long-distance run or not hit your protein macros because you ran out of a protein shake? 
  26. Would you rather go snorkeling in Hawaii or the Philippines? 
  27. Would you rather talk to your favorite athlete for five minutes or have a season pass to their matches? 
  28. Would you rather have to wrestle a hippo or a seal? 
  29. Would you rather be as fast as a jaguar or as strong as an ant? 
  30. Would you rather listen to the same playlist during every workout or not listen to any music? 

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Relationship Would You Rather Questions

Some of these dating scenarios are silly, while others are more serious. Both can be a launching point to talk with your friends about what you value and look for in a partner. 

  1. Would you rather fall in love with a mermaid/merman or a centaur? 
  2. Would you rather your significant other sneeze whenever they kiss you or start coughing when you hold hands? 
  3. Would you rather be with someone who eats the same food every day or watches the same movie once a month? 
  4. Would you rather date someone more sensitive or more logical? 
  5. Would you rather be in a relationship where one partner stays home and cares for the household while the other is the breadwinner or have both partners work outside the home and contribute to the family’s upkeep? 
  6. Would you rather have a “meet cute” with a stranger or be set up by mutual friends? 
  7. Would you rather have a long or short engagement? 
  8. Would you rather change something about your partner or change something about yourself? 
  9. Would you rather your partner burped after every meal or stepped in gum whenever you went for a walk? 
  10. Would you rather your partner be passionate about their job but work 60-hour weeks or feel “meh” about their job but work 40-hour weeks? 
  11. Would you rather move to another country to be with the love of your life or have them move to you and help them adapt to your country? 
  12. Would you rather your significant another offer to cook dinner or spontaneously bring you home a bouquet? 
  13. Would you rather have a big wedding you’ve always dreamed of or put a downpayment on the house with your partner? 
  14. Would you rather spend your honeymoon in a resort on Bora Bora or on a cruise in the Mediterranean? 
  15. Would you rather date someone who shares all your same hobbies or has an entirely different set of hobbies you can learn from? 
  16. Would you rather spend date night with a home-cooked meal and meaningful conversations or go to town for a memorable evening with your partner? 
  17. Would you rather spend the first five years of marriage without kids or start having children immediately? 
  18. Would you rather your significant other give you lots of sweet compliments or listen well to the challenges you’re facing? 
  19. Would you rather nervously sweat on every first date or throw up before leaving the house because you’re so stressed? 
  20. Would you rather date someone long-distance for several years or end the relationship despite still loving them because long-distance would be too hard? 
  21. Would you rather your significant other write a song inspired by you or paint your portrait?
  22. Would you rather date someone your family didn’t approve of or your friends didn’t approve of? 
  23. Would you rather fall in love with your book crush or favorite TV character? 
  24. Would you rather know that your partner will ask you to marry them, or would it be a surprise? 
  25. Would you rather have a destination wedding with only close family and friends or have a wedding intimate to home with all of your friends? 

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Would You Rather Questions to Help You Get to Know Someone’s Personality and Preferences Better 

Would you rather it be a great group game, but it can also be used in one-on-one settings to get to know someone better? These questions can help you understand someone’s preferences in different situations. 

  1. Would you rather spend a Saturday in the city shopping or sightseeing? 
  2. Would you rather go to a farmers market or sleep in and have a relaxed morning? 
  3. Would you rather go home on a Friday night and put on cozy PJs or go out with friends? 
  4. Would you rather speak your mind or keep the peace? 
  5. Would you rather always be a little uncomfortably hot or a little uncomfortably cold? 
  6. Would you rather travel 10 minutes or 100 years to the future? 
  7. Would you rather throw a dinner party for 15 guests or organize a picnic with 50 members of your family? 
  8. Would you rather host a big group gathering with many people you know and introduce them to one another or have smaller get-togethers where everyone is already friends? 
  9. When something has happened that needs to be resolved, would you rather the other person be direct and let you know what they’re upset about or take longer to say what’s on their mind but express it gently? 
  10. Would you rather lend someone your car or offer to give them a ride? 
  11. Would you rather spend a rainy afternoon reading a long book with a warm cup of tea or getting some projects around the house finished? 
  12. Would you rather stay late at work to finish everything you need to do or bring work home to complete it from the comfort of your home? 
  13. Would you rather repeatedly go to the same place for vacation or never be able to return somewhere you’ve already visited? 
  14. Would you rather see a Broadway show or a professional ballet? 
  15. Would you rather host a party with five of your closest friends or a potluck that anyone is welcome to come to? 

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Final Thoughts: Take the Question a Step Further

When you’re using questions like these to get to know someone better, try finding ways to keep the conversation moving forward so you can get to know them better. 

Here are some tips to segway a question into a conversation:

  • Ask them why. If someone answers and doesn’t give much of an explanation, try asking why they would choose that answer. Here are two ways to do that, depending on whether you also agreed with them or answered differently! 
  • “Really? That’s so interesting. I chose the other option for these reasons [give a few sentences with your reasoning]. Why did you feel differently about it? 
  • “I agree! After all, [give some of your reasoning for giving that answer]. Why did you choose this option? 

By sharing a bit about why you chose the way you did, you can help it feel less intimidating to someone who may be introverted

  • Be engaged with the speaker. If someone volunteers how and why they chose the response they did, be sure to engage with what they’re saying. You can do this non-verbally by making eye contact, nodding your head, and leaning in your seat. Once they finish speaking, you can bounce off what they’ve said or ask a follow-up question.
  • If you’re playing with a group, try asking the quieter members what they think. First, wait for a few rounds before doing this. This will give everyone a few minutes to get a feel for what is happening and decide when they are ready to jump into the conversation. If you are facilitating the group (for example, in a classroom setting), you may want to draw people into the game. Try asking a question and, after a little while of more chatty people talking, casually say, “[Name], what are your thoughts—mountains or ocean?” 

If you’re looking for more ways to spark conversations, check out these killer conversation starters.

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