Chill Out with 100 Winter Would You Rather Questions For Middle Schoolers!

Winter is the perfect time for cozy gatherings, indoor fun, and sparking imaginations. And what better way to do that than with some hilarious and thought-provoking Winter Would You Rather Questions For Middle School? Get ready to debate the tough choices, share some laughs, and maybe even learn a thing or two about your friends and classmates.

Why Winter Would You Rather Questions Rock for Middle Schoolers

So, what exactly are “Winter Would You Rather Questions For Middle School”? Simply put, they’re questions that present two scenarios, asking you to choose which one you’d prefer, even if both options are a little silly, strange, or challenging. They’re super popular because they’re a fantastic way to break the ice, encourage critical thinking, and reveal what people really value. Winter Would You Rather questions are a fun, engaging, and simple way to interact in the classroom, with friends, or even just to pass the time on a snowy day.

Think of them as mini-dilemmas designed to get you thinking outside the box. They aren’t about right or wrong answers, it’s all about personal preference and justifying your choice. Plus, they can be used in so many different ways! Teachers might use them as quick writing prompts to get students engaged at the start of class. Friends might play a round at a sleepover, leading to some hilarious debates. Families can use them during long car rides to keep everyone entertained. The possibilities are endless!

They are also a good way to gauge what your students enjoy or feel uneasy about. Here are some examples of situations where they can be used:

  • Classroom icebreakers
  • Party games
  • Conversation starters

Winter Wonderland Dilemmas

  1. Would you rather only be able to drink hot chocolate or only be able to drink apple cider for the rest of the winter?
  2. Would you rather have a snowball fight with snowballs that never melt or go sledding on a hill that never ends?
  3. Would you rather build a snowman that comes to life and follows you everywhere or have a pet penguin that wears a tiny hat?
  4. Would you rather live in an igloo made of ice or a gingerbread house made of candy?
  5. Would you rather have the power to control snow or ice?
  6. Would you rather wear a snowsuit all day, every day, or wear shorts and a t-shirt all day, every day?
  7. Would you rather be trapped in a snow globe or a giant inflatable snow globe?
  8. Would you rather have a winter vacation in the mountains or at the beach?
  9. Would you rather have a magical scarf that keeps you warm forever or a magical pair of gloves that never get wet?
  10. Would you rather only be able to eat peppermint-flavored things or gingerbread-flavored things for the entire winter?
  11. Would you rather have to sing carols every time you enter a room or have to wear reindeer antlers everywhere you go?
  12. Would you rather have a snow day every week or have no homework for the rest of the year?
  13. Would you rather have a robot that shovels your driveway or a robot that decorates your house for the holidays?
  14. Would you rather be able to speak to animals or control the weather?
  15. Would you rather get socks or underwear for Christmas every year?
  16. Would you rather find a real snowman or an abominable snowman in your yard?
  17. Would you rather be able to ice skate perfectly or ski perfectly?
  18. Would you rather be stuck on a ski lift or a Ferris wheel?
  19. Would you rather get a white elephant gift that’s actually good or a very expensive gift that you don’t like?
  20. Would you rather live in Santa’s Village or with elves in a tree?
  21. Would you rather have a pet polar bear or a pet artic fox?
  22. Would you rather be famous for building the best snowman or making the best snow angels?
  23. Would you rather have a magical sled that can fly you anywhere or magical skates that never slip?
  24. Would you rather be a world-famous snowman builder or the world’s best ice skater?
  25. Would you rather drink warm hot chocolate or warm apple cider on a cold winter night?
  26. Would you rather get stuck in a blizzard or an ice storm?
  27. Would you rather get buried in snow or get lost in a corn maze?
  28. Would you rather play in the snow or sit inside by a fire?
  29. Would you rather go ice fishing or winter hiking?
  30. Would you rather be able to breathe under snow or walk across ice without slipping?
  31. Would you rather always wake up to a white Christmas or never have to shovel snow again?
  32. Would you rather be able to make snow angels that can sing or snowballs that can talk?
  33. Would you rather have a snowplow or a snow blower?
  34. Would you rather only be able to wear one color of winter clothing?
  35. Would you rather live in a place that never snows again or that has winter all year round?

Holiday Happenings and Conundrums

  1. Would you rather only be able to give presents or only be able to receive presents during the holidays?
  2. Would you rather have to spend Christmas with the Grinch or Krampus?
  3. Would you rather eat only Christmas cookies for a week or only eat candy canes for a week?
  4. Would you rather have a Christmas tree that’s so big it touches the ceiling or so small it fits in your pocket?
  5. Would you rather be in charge of decorating the Christmas tree or wrapping all the presents?
  6. Would you rather get a visit from Santa Claus or the Easter Bunny?
  7. Would you rather have all your presents arrive before Christmas or after Christmas?
  8. Would you rather travel around the world with Santa on Christmas Eve or work at the North Pole all year round?
  9. Would you rather be on the naughty list or the nice list?
  10. Would you rather have to wear an ugly Christmas sweater every day or sing carols every time you enter a room?
  11. Would you rather never receive another Christmas card again or have to write 100 Christmas cards?
  12. Would you rather have your house decorated for Christmas or your car?
  13. Would you rather spend Christmas at home with your family or at a tropical resort?
  14. Would you rather watch a Christmas movie every day for a month or listen to Christmas music every day for a month?
  15. Would you rather be forced to attend every family gathering or have to cook Christmas dinner?
  16. Would you rather have to explain to Santa why you are on the naughty list or explain to your parents why you failed a test?
  17. Would you rather only be able to watch one holiday movie for the rest of your life or listen to one holiday song for the rest of your life?
  18. Would you rather be in charge of cooking the holiday feast or in charge of cleaning up afterward?
  19. Would you rather get the worst gift in the world or not get any gifts at all?
  20. Would you rather celebrate Christmas in July or July on Christmas?
  21. Would you rather get a stocking full of coal or only receive gift cards to stores you don’t like?
  22. Would you rather only receive clothing as gifts for the rest of your life or only receive food?
  23. Would you rather spend Christmas Eve caroling or watching your favorite holiday movie?
  24. Would you rather have a fake Christmas tree or a real one that doesn’t smell?
  25. Would you rather wear a full-body snowman costume or an elf costume for the holiday season?
  26. Would you rather be a reindeer pulling Santa’s sled or one of Santa’s elves in the workshop?
  27. Would you rather attend the perfect Christmas party or have a quiet night alone during the holiday?
  28. Would you rather have to buy presents for your entire class or do community service every weekend?
  29. Would you rather get a lump of coal every year or never get any presents again?
  30. Would you rather be the only one in your family who doesn’t get presents or the only one who gives them?
  31. Would you rather wear a Santa hat every day or reindeer antlers for the entire season?
  32. Would you rather have all the lights on your house be pink or all be green?
  33. Would you rather receive a fruitcake every year or a Christmas sweater?
  34. Would you rather only be able to give handmade gifts or only be able to receive them?
  35. Would you rather have Christmas in the summer or the summer in Christmas?

New Year’s Eve Nightmares and Dreams

  1. Would you rather have to kiss someone you don’t like at midnight or spend New Year’s Eve alone?
  2. Would you rather have a New Year’s resolution that’s impossible to keep or not make any resolutions at all?
  3. Would you rather be stuck in a time loop, reliving New Year’s Eve forever, or skip ahead a year into the future?
  4. Would you rather have to wear a silly party hat all night or carry around a noisemaker that never stops making noise?
  5. Would you rather have a magical fortune cookie that always tells the truth or one that always tells lies?
  6. Would you rather be able to predict the future or change the past?
  7. Would you rather have to write a 10-page essay about the past year or give a five-minute speech about your hopes for the future?
  8. Would you rather have a New Year’s Eve party at your house or go to a party at someone else’s house?
  9. Would you rather stay up all night celebrating or go to bed early and wake up refreshed?
  10. Would you rather eat black-eyed peas and collard greens for good luck or a fancy dinner with champagne?
  11. Would you rather set off fireworks or watch a fireworks show?
  12. Would you rather make a toast to the new year or listen to someone else’s toast?
  13. Would you rather have to wear a sequined dress or a tuxedo to a New Year’s party?
  14. Would you rather be the only one who has no fun at a New Year’s party or be the one who breaks something expensive?
  15. Would you rather have to clean up after a party or be responsible for all the planning?
  16. Would you rather host the worst New Year’s Eve party or not get invited to any parties for the year?
  17. Would you rather wake up with a bad hangover or be super tired and miss all the celebrations?
  18. Would you rather be able to attend one New Year’s Eve party from history or skip ahead one year to the future?
  19. Would you rather have to write a speech for New Year’s or be the one who has to clean up afterwards?
  20. Would you rather have to spend every New Year’s Eve working or never get a raise for the rest of your life?
  21. Would you rather have the power to rewind the past year or fast forward through the next one?
  22. Would you rather have to make a toast or sing in front of people during New Year’s celebrations?
  23. Would you rather have to write an essay about the past year or a song for the new one?
  24. Would you rather always have to stay up until midnight or always wake up early the next day?
  25. Would you rather have to spend the night with your most annoying relative or be stuck doing chores?
  26. Would you rather get coal in your stocking or miss the ball drop on TV?
  27. Would you rather host an epic New Year’s Eve bash or travel somewhere exotic and have a quiet night?
  28. Would you rather have to spend the holiday with your family or a group of strangers?
  29. Would you rather dance all night or play board games until the clock strikes twelve?
  30. Would you rather have your wish come true or someone else’s?
  31. Would you rather have a terrible start to the new year and an amazing finish or an amazing start and a terrible end?
  32. Would you rather have a New Year’s Eve party with a strict dress code or no dress code at all?
  33. Would you rather accidentally reveal someone’s secret at midnight or have your own secret revealed?
  34. Would you rather write a New Year’s card to your future self or receive a New Year’s card from your past self?
  35. Would you rather get stuck reliving the same New Year’s Eve party over and over or never be able to celebrate New Year’s again?

So there you have it – a avalanche of Winter Would You Rather Questions For Middle School! Whether you’re looking for a fun way to connect with friends, liven up a classroom, or simply pass the time on a cold winter day, these questions are sure to spark some interesting conversations and maybe even reveal a few hidden truths along the way. Enjoy the winter wonder and have a blast with these “would you rather” scenarios!