Winter is the perfect season for cozying up with loved ones, sipping on hot cocoa, and having meaningful conversations. Whether you’re sitting by the fire, on a long road trip, or gathered around the dinner table, these conversation starters can add a touch of fun and warmth to your family time.
I’ve divided these into categories so you can choose the best questions for your setting—perfect for kids, teens, and the whole family. Don’t forget to grab my free printable with all the conversation starters!
Winter Conversation Starters
After-School Conversation Starters for Younger Kids
Younger kids are brimming with imagination, so these questions are designed to let their creativity shine!
- If you could build a snowman that comes to life, what would you want it to do?
- What’s your favorite thing about winter, and why?
- If you were a penguin, what winter adventure would you go on?
- Would you rather sled down the biggest hill ever or have a snowball fight with your favorite cartoon characters?
- What’s the best way to stay warm in winter—hot cocoa, a blanket, or snuggles?
- If you could decorate a tree with anything besides ornaments, what would you use?
- Would you rather live in a gingerbread house or a snow castle? Why?
- What’s your favorite kind of cookie to eat during winter?
- If you could make your own winter holiday, what would you celebrate?
- What’s the funniest thing that’s ever happened to you in the snow?
After-School Conversation Starters for Teens
Teenagers can be hard to engage, but these questions mix humor, pop culture, and just enough curiosity to get them talking.
- If you could invite one celebrity to a holiday party, who would it be and why?
- Would you rather get snowed in for a week with no Wi-Fi or no snacks?
- What’s the ultimate playlist for a winter road trip?
- If you had to wear one holiday sweater every day for a month, what would it look like?
- What’s your dream winter vacation—skiing in the mountains, a cabin in the woods, or a tropical beach?
- Would you rather star in a cheesy holiday movie or direct one?
- What’s the weirdest winter trend you’ve seen online this year?
- If you could give your pet a winter-themed makeover, what would it look like?
- What’s your go-to snow day snack or drink?
- If you could time travel to one historical winter moment, where would you go?
Dinner Table Conversation Starters for the Winter
These questions are perfect for family gatherings and are designed to include everyone, no matter their age.
- What’s your funniest or most embarrassing winter memory?
- If you could create a family tradition this winter, what would it be?
- Would you rather spend winter in a cozy log cabin or on a luxury ski resort?
- If you had to give everyone in the family a winter-themed nickname, what would they be?
- What’s the best winter dessert—pie, cookies, or hot chocolate?
- If you could invent a new winter sport, what would it be?
- What’s your all-time favorite winter movie or show to watch as a family?
- If you could have any animal as a sled team, what would you pick?
- What’s the most creative thing you’ve ever done with snow?
- Would you rather live where it’s always winter or always summer?
Holiday-Focused Conversation Starters
Holidays are full of stories, traditions, and laughter. These questions dive into the magic and memories of the season.
- What’s the best holiday gift you’ve ever received?
- If you could create your own holiday, what would it be called, and how would you celebrate?
- What’s your favorite holiday song, and why do you love it?
- If you could travel anywhere in the world to celebrate the holidays, where would you go?
- What’s one funny or unexpected thing that happened during a past holiday celebration?
- If you could eat only one holiday treat for the rest of the season, what would it be?
- What’s your favorite holiday tradition, and what makes it special?
- If you could have a holiday dinner with any fictional character, who would it be?
- What’s the weirdest or funniest holiday decoration you’ve ever seen?
- If the holidays had a mascot besides Santa, who or what would it be?
Winter “Would You Rather” Questions
Nothing gets the family giggling faster than a good round of “Would You Rather.” Here are some winter-inspired ones to try.
- Would you rather build the world’s biggest snowman or the fastest sled?
- Would you rather have snow that tastes like marshmallows or rain that smells like peppermint?
- Would you rather wear itchy holiday sweaters every day or listen to the same holiday song on repeat?
- Would you rather go ice skating on a frozen lake or skiing down a snowy mountain?
- Would you rather decorate 1,000 holiday cookies or wrap 1,000 presents?
- Would you rather live in a snow globe or a gingerbread house?
- Would you rather always have cold toes or always have a red nose in winter?
- Would you rather eat only candy canes for a week or only fruitcake for a month?
- Would you rather open one small present every day in December or one giant present on Christmas morning?
- Would you rather meet Santa or ride in his sleigh?
Click here to grab your FREE Printable!
Winter is a magical time to connect with your family, share stories, and create memories that will last a lifetime. Use these conversation starters during dinners, car rides, or cozy evenings to keep the laughter and bonding going all season long! Which question are you going to try first?
Send me a message on Instagram and let me know how your family answered!
Emily, a seasoned travel writer and editor, has traversed the Western United States, calling places like California, Arizona, Wyoming, Montana, and now Washington her home. With a passion for exploring and a particular fondness for unique Airbnb stays, she brings a wealth of experience and a fresh perspective to every piece she writes.
