Holiday Would You Rather Questions: Christmas, Hanukkah, New Year’s and Winter Break

November 2026  ·  54 questions

Holiday would you rather questions are quick two-choice picks that mix Christmas, Hanukkah, New Year’s and winter break, like “Would you rather build a snowman or a snow fort?” or “Would you rather eat a holiday cookie or a latke?” Below are 54 clean, easy questions in five groups, so mixed families, classrooms and holiday parties can all play together, whatever they celebrate.

Want to play right now? Tap a choice on the card below, then hit next for another question.

The holidays at a glance this year

The season is packed. Here are the big days, so you can pull the right questions for the right week:

54 holiday would you rather questions

Christmas

• Would you rather decorate the tree or decorate a gingerbread house?
• Would you rather open one gift on Christmas Eve or save every gift for Christmas morning?
• Would you rather have a real Christmas tree or an artificial one that never drops a needle?
• Would you rather find a gift from Santa that’s exactly what you asked for or a surprise you never knew you wanted?
• Would you rather go caroling around the neighborhood or drive around looking at Christmas lights?
• Would you rather wear matching family pajamas or an ugly Christmas sweater all day?
• Would you rather bake Christmas cookies or decorate them?
• Would you rather ride in Santa’s sleigh or help out in his workshop for a day?
• Would you rather have a white Christmas or a sunny 70-degree Christmas?
• Would you rather watch your favorite Christmas movie or a brand-new one?
• Would you rather have a stocking full of candy or a stocking full of tiny toys?
• Would you rather leave out cookies for Santa or carrots for the reindeer?

Hanukkah

• Would you rather light the menorah or be the first to spin the dreidel?
• Would you rather eat latkes with applesauce or latkes with sour cream?
• Would you rather have a jelly doughnut or a chocolate-filled doughnut?
• Would you rather win a big pile of chocolate gelt at dreidel or get one small gift every night for eight nights?
• Would you rather make your own menorah or decorate your own dreidel?
• Would you rather eat latkes every night of Hanukkah or doughnuts every night of Hanukkah?
• Would you rather have a Hanukkah party with all your cousins or a quiet night of candles with just your family?
• Would you rather give eight small gifts or one big gift?
• Would you rather sing Hanukkah songs or play dreidel all evening?
• Would you rather have blue and silver decorations everywhere or a menorah glowing in your front window?

New Year’s

• Would you rather stay up until midnight or celebrate an early “kids’ midnight” at 7 p.m.?
• Would you rather bang pots and pans at midnight or throw confetti at midnight?
• Would you rather make a New Year’s resolution you’ll keep or one that’s fun to try?
• Would you rather have a New Year’s Eve sleepover or a New Year’s Day pancake breakfast?
• Would you rather write a letter to yourself to open next New Year’s or make a time capsule for 10 years from now?
• Would you rather watch fireworks in person or watch the celebrations on TV?
• Would you rather wear a sparkly party hat or silly New Year’s glasses?
• Would you rather make a list of your favorite moments from this year or a list of things you want to do next year?
• Would you rather count down with noisemakers or count down with balloons dropping from the ceiling?
• Would you rather eat 12 grapes at midnight or eat black-eyed peas for luck on New Year’s Day?

Winter break

• Would you rather build a snowman or build a snow fort?
• Would you rather go sledding or go ice skating?
• Would you rather have a pajama day or a movie marathon day?
• Would you rather sleep in every day of break or wake up early for fun every day?
• Would you rather go to Grandma’s for the holidays or have everyone come to your house?
• Would you rather drink hot cocoa with marshmallows or warm apple cider with a cinnamon stick?
• Would you rather have a snowball fight or make snow angels?
• Would you rather do a giant puzzle with your family or play board games all afternoon?
• Would you rather build a blanket fort or have an indoor picnic by the fire?
• Would you rather have two weeks of snow days or two weeks of sunny beach days?
• Would you rather go on a winter vacation or stay home and do something fun every day?
• Would you rather catch snowflakes on your tongue or find the biggest icicle in the neighborhood?

Mix-and-match holiday picks

• Would you rather eat a holiday cookie or a latke?
• Would you rather celebrate in the snow or celebrate on a beach?
• Would you rather get a gift you can play with or a gift you can make something with?
• Would you rather make a homemade gift for someone or pick out the perfect store-bought gift?
• Would you rather have holiday lights on every house on your street or the biggest light display in town at your house?
• Would you rather learn how another family celebrates or teach someone your family’s favorite tradition?
• Would you rather do a holiday craft or bake a holiday treat?
• Would you rather give a gift or get a gift?
• Would you rather spend the holidays in the mountains or in a big city with lights everywhere?
• Would you rather start a new family tradition this year or keep every tradition exactly the same?

Why a mixed holiday deck works

Here’s the thing about December parties: not everyone celebrates the same holiday. A classroom might have kids who light the menorah, kids who hang stockings and kids who mostly care about two weeks off school. A Christmas-only game leaves some of them out. A mixed deck lets everyone shine.

It’s also a sneaky way to learn about each other. When someone picks “light the menorah” and explains why, the rest of the room hears about a tradition they might not know. Kids love being the expert.

How to play holiday would you rather

• Classic. Read a question, everyone picks, then each person says why. That’s it.
• Four corners. In a classroom, point to one side of the room for each answer and have kids walk to their pick. Great for burning off pre-break energy.
• Guess the grown-up. At a family party, kids guess what Grandma will pick before she answers.
• One a day. Use one question each morning from December 1 until break. Our classroom would you rather page has more ways to run it.
• Party round. Before gifts or dessert, go around the table with one question per person.

Which questions fit which group?

More holiday questions

Want a deck that’s all Christmas? The Christmas edition has plenty, and the Christmas would you rather questions for kids are perfect for little ones. For the days after the gifts are open, try the winter edition, and save the New Year’s edition for December 31.

What most hosts get wrong

Asking questions with a “right” answer. “Would you rather have the holidays or no holidays?” isn’t a question; everyone answers the same way. The best holiday questions put two good things side by side, like latkes or doughnuts, sledding or skating. That’s where the fun arguments start.

When you’re ready, tap the button on the card above to play all 54 holiday questions in the full Would You Rather game.

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