25 Winter Date Ideas — Cheap and Fun Ways to Connect!

Dec 22, 2021 | Date Night, Marriage

Connecting with your sweetie is SO important, but sometimes it's a little harder to do when it feels like you're stuck inside in the cold weather. Never fear, we've come up with the best cheap or free winter date ideas you'll both love!

Couple hugging outside during the winter, from Fun Cheap or Free

Olaf said it best… “Winter's a good time to stay in and cuddle!” But it's also a good time to get out and enjoy each other's company, too! It's time to quit twiddling your thumbs, trying to figure out what to do as a couple, and have fun, already.

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Don't worry, we've got some great cheap and fun ways to connect with your special someone during this cold season! Try out a few (or all!) of our winter date ideas and enjoy each other's company before the warm weather comes back and you have to wait until next year for some of these fun date ideas. Let's get started!


Couple watching movie on the couch, from Fun Cheap or Free

Who says you have to leave the house to have fun? We have some epic winter date ideas you definitely won't want to miss! Whether you plan on keeping warm inside, getting outside to play, or creating some foodie masterpieces, we've got something for everybody. No car needed!


  • Cozy Up – What's more romantic than cozying up with your favorite person on the couch?! Bonus points if you're curled up in a super soft blanket.
  • Play Your Favorite GamesGame night is always fun! Grab your favorite board game, like Ticket to Ride, or some cards, then get to it.
  • Design Your Dream Home – This is always a fun one and it sets your eyes (and budget) on the prize! If you're already living in your dream home, then daydream about another goal.
  • Go Camping in Your Living Room – Who says you need to go outside to camp? Set up in your living room and have a blast!
  • Have a Movie Marathon – Watch your favorite movies or series together or discover something new! Harry Potter, anybody?
  • Plan a Vacation – It's always fun to plan for the future! If you've been saving for a vacation, then take the time to plan it now. You can also plan a staycation at home if that's more your style! You can still have plenty of fun in your hometown.


Couple building a snowman during winter date, from Fun Cheap or Free
  • Build a Snowman – Nothing says winter quite like snow! Get outside, build a snowman, and dress it up for good measure. You could also turn this into a fun competition to see who can build one the quickest! (Psst… No snow? No problem! Just grab some white playdough, channel your inner child, and make them inside!)
  • Have a Snowball Fight – Here's another fun winter date idea! Get out in the snow and have a snowball fight, either with each other, the rest of the family, or even with friends. Those of you who aren't lucky enough to get snow can even find fake snowballs to throw at each other in the house! Better yet, recycle some used paper and make your own snowballs!
  • Sit Around the Fire Pit Outside – Turn the heat up and fire up the fire pit! It's fun to unplug, enjoy being outside, and have fun just talking and being with each other.
  • Go Stargazing – Winter is the perfect time of year to look at the stars! The cold air means you'll get a clear view of the beautiful sky. You'll be able to see lots of constellations. Who knows? You may even get lucky enough to see a shooting star or meteor!
  • Winter Photoshoot – Go to your backyard and have a winter photoshoot! It can be as cute or goofy as you want… Just remember to have fun and not get stressed. 😉


Hot chocolate on a counter, from Fun Cheap or Free
  • Make Homemade Hot Chocolate – Hot cocoa is always delicious, but it's extra good when you make it from scratch at home! You'll go bananas over our Mexican hot chocolate recipe, we promise.
  • Have an Indoor Picnic – Who says you need to go outside to have a picnic?! Use our best tips and picnic ideas and picnic on your living room floor!
  • Make Chocolate Covered Strawberries – Why yes, Valentine's Day is technically still during the winter months! So try your hand at making chocolate covered strawberries and be amazed at how easy and cheap they are versus buying those expensive ones at the store.
  • Have a Chili Contest – Both of you get in the kitchen and see who can make the best pot of chili… without a recipe! It turns a delicious meal into a fun challenge.
  • Roasted Marshmallows – Got a fireplace or fire pit? Bust out the marshmallows! Or go the extra mile and make some delicious s'mores. Feel free to use any leftover holiday candy to take them up a notch!
  • Bake Bread – Can bread be a love language? Because it's totally ours. 😉 Try your hand at homemade white bread, French bread, rustic bread, or even banana bread!
  • Create Your Own Soup – This is a fun way to not only shelf cook, but also spend some quality time together in the kitchen! Grab whatever meats, veggies, liquids, and grains you need to use up and make your own soup from scratch. You really can't go wrong throwing it all together and you can be proud of the finished masterpiece.

Pro Tip: While you're making your delicious meals and bread, plan to freeze what you won't eat! It'll give you an easy freezer meal for those nights when you just don't feel like cooking. Score!


Couple skating on ice during winter date, from Fun Cheap or Free

Alright, so you've had enough of the house and you're ready to get in the car and go somewhere! Don't worry, we've got some awesome winter date ideas that you're sure to love.

  • Find a Drive-In Movie – This is always so fun! If there's a drive-in movie nearby, then take full advantage of it. Take your own drinks and snacks and you have a cheap and fun winter date idea!
  • Take a Stroll Around Downtown – Go exploring and find a quaint downtown to walk hand-in-hand around. We have a great post on how to find fun things to do near you to help with this! Don't forget to bundle up if it's chilly outside. A travel mug full of your favorite warm drink will surely help to keep you warm!
  • Go Hiking – It's always fun to go hiking at different times of the year to see how nature and animals change and react to the seasons. Bundle up and get outside! We promise you'll warm up after you start walking. 😉
  • Take Advantage of the Snow – If you live somewhere that gets snow during the winter (or it happens to be one of those rare occasions where you live), take full advantage of it! Go sledding, skiing, snowboarding, or snowmobiling. Enjoy it while it lasts!
  • Find a Carriage Ride – Does anywhere near you offer carriage rides in the street or sleigh rides in the snow? Make it a point to find one then go do it! Take some warm blankets to cuddle up under and don't forget a nice warm drink to keep you warm. Check Groupon for a good deal!
  • Go Ice Skating – Talk about a great winter date idea! Find an ice skating rink or a (*well-frozen*) pond and take to the ice. Work on your couples figure skating or play a fun one-on-one game of hockey. Winner gets a massage!
  • Volunteer – It's so important to give back to the community, so why not make a date out of it?! Volunteer at a local soup kitchen or animal shelter, or take a trip together to buy some much-needed non-perishable items for the food pantry.

Pro Tip: Save up for some of these fun winter date ideas if they're a little too pricey for you! Skip the drive-through or eating out for the week and put that money in your date fund. In no time at all, you'll have the money saved for these fun ideas that cost a little money!


Sometimes it can feel like there's absolutely NO time for fun dates because you're so busy doing all. the. things. Laundry, cleaning the house, running kids to extracurricular activities, the list just goes on and on… Well not anymore, honey! It's time to invite Productivity Boot Camp into your life. Our fun, online video program will help you tackle the pain points in your life, set up systems, and help you make more time in your life for what's important to you! Check it out…

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Alright, well there you go! Twenty-five of our favorite winter date ideas that are just ready and waiting for you and your sweetie. What's your favorite date when it's cold out? Share it with us in the comments below!

Image with text that reads "25 cheap and easy winter date ideas" from Fun Cheap or Free

Looking for even more fun date ideas?

Happy dating!


  1. Alejandra Martin

    Can you turn this into an amazing printable for us? I love to print them out and laminate them to keep them in my family binder! =)

    • Fun Cheap or Free

      That’s definitely the plan for in the future! 🙂


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