Coming up with winter date ideas can be difficult and planning dates in general can be a challenge at times too. Not to worry, we’ve got you covered! Think outdoor dates are exclusively reserved for warmer weathered seasons? Definitely think again. As long as you have a loving partner and a nice cozy jacket, you’ll find an abundance of unique outdoor winter date ideas! For the homebodies out there, we didn’t forget about you – don’t worry. 

Coming up with cute winter date ideas

Winter dates have such a wide range of activities, they truly are endless! Here are a few indoor and outdoor winter date ideas:

Outdoor Winter Date Ideas

🎶 Baby it’s cold outside ~~ 🎶 and it will be for a little while! Why not make the best of this cool weather and have the perfect outdoor winter date planned for you and your loved one! Getting out and enjoying the winter breeze might be exactly what you need after being cooped up at home due to the pandemic. Here are some ideas for your next winter outdoor date!

Outdoor Date Ideas:

  • A winter picnic with tons of heating pads and warm blankets
  • A day of sledding or a good old fashioned snowball fight
  • Snowman making competition
  • Go on a hike
  • Go Ice skating and drink some delicious hot chocolate
  • Soak in an outdoor hot tub

Indoor Winter Date Ideas

Sometimes, a cozy indoor date is just what you and your loved one need. If it snows wherever you live, you know how much of a hassle it is to get from point A to point B – this makes indoor dates that much more necessary! Here are some ideas for your next indoor winter date!

Indoor Date Ideas:

  • Board game night next to a warm fire
  • Cook a romantic dinner for two together
  • Order takeout and watch a movie
  • Make a relationship scrapbook
  • Give each other a massage
  • Toast marshmallows indoors

Well, what are some cold weather date ideas?

Winter is probably the best season to schedule a lowkey date night. With the weather cooling up, the indoor and outdoor date ideas are endless. To add to the lists above, here are some date ideas specifically made for the cold weather:

Cold Weather Date Ideas

  • Host a hot chocolate competition
  • Do a holiday themed craft
  • Look at Christmas lights
  • Go holiday shopping
  • Try a new winter sport
  • Have a winter themed cocktail night
  • Take a carriage ride with (make sure to take some warm blankets)

A winter couple photoshoot can be a real winner

There’s nothing more magical than a photoshoot in the snow or in front of your beautifully decorated holiday home. What’s more magical than holding your loved one close while the snow elegantly falls around you? Take this season as an opportunity to get some of the best shots!

Frankly speaking, some of the best couple shots are candid ones! So definitely do something you both incredibly enjoy. The happiness you feel will be sure to reflect in those breathtaking pictures. 

Outdoor fun date ideas for couples in winter

While the list for outdoor winter activities can be endless, here are some fun winter date ideas for couples living in Chicago and New York:


Fellow Chicagoans, buckle up for a lengthy winter. To keep you a bit sane, here are some date night ideas for you and your special someone!

Chicago Ideas 

New York 

Most New Yorkers out there aren’t the biggest fan of winters. We get it – with all the slush and the wind whipping out of control how can you even enjoy a date night? Here are some ideas that might make it just a bit more enjoyable.

New York Ideas

  • Enjoy a cozy night at the bar in Little Italy
  • Dine in at Luzzo’s La Pizza Napoletana, East Village
  • Adventure through the amazing pieces at The MET
  • Let loose at Bryant Park for some ice skating
  • Be on the hunt for a speakeasy

Fun free date ideas for winter

Most of the activities listed above are absolutely free! Other than museum visits, the occasional rentals for sporting dates, and the amount spent on supplies for home cooked meals, these activities come with low costs and are mostly free if you’re already in possession of supplies!


What can you do on a date in the winter?

There’s so many activities you can do for a winter date! From visiting museums, to ice skating, all the way to cooking homemade meals and having a cozy movie night – the options are endless!

What can I do with my girlfriend on a cold day?

You can stay home and have a cooking competition, play board games, have a craft night, roast some marshmallows by the fireplace, and end the night with a movie.

What can you do with your boyfriend when it’s cold outside?

If they would prefer to stay home, cook some dinner with them, challenge them to a game, look through old photo books together and even start scrapbooking a future!

Where should I go on a first date in the winter?

The best first winter dates always start with an ambient restaurant and can also include arcades, bars, carriage rides, snowball fights, and even a movie night. 

What is cuffing season?

Cuffing season refers to individuals getting into relationships during the colder months of the year. Relationships that start during “cuffing season” stereotypically don’t last very long and tend to die out as the warmer months come along! But who knows, you might be one that goes against those stereotypes!


Although finding winter date ideas can be difficult, especially with seasonal depression rolling around, the options are truly endless. Whether you’re an outdoor person or a homebody there is definitely a date idea out there for you! We hope the items listed in this blog have helped and can’t wait for your next extraordinary winter date night with that special someone!

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