7 Incredibly Creative, Cheap, and Cozy Winter Date Ideas

December 26 and the days following are kind of a bummer.

Now that all the excitement of Christmas has passed, the upcoming months can feel mighty dreary and boring (if only we had a stack of presents awaiting us every morning).

Even in our relationships, we may be tempted to get complacent, letting one day blur into the next until the warmer weather comes to lift our spirits.

I think there are ways we can make the most of the post-Christmas season and even deepen our relationships during these cold months.

How? Glad you asked.

The point of winter is that not all the time has to be “busy.” Try enjoying each other’s company without necessarily doing something together.

When you think of going on a date, you most likely think of going to do something. The movies, dinner, a leisurely walk around the park . . . The warmer, prettier months are understandably more conducive to these types of activites; however, I think winter offers us something different—but just as important (and romantic).

And no, I’m not talking about “Netflix and chill.”

The winter months graciously provide a quieter, slower time of year, which can help us nurture our relationships and achieve a deeper level of intimacy.

To show you how winter can help us grow in our relationships, here are some cheap and cozy winter date and activity ideas that will help you keep your relationship fresh and fun—even if the “weather outside is frightful.”

1. Start a journal

It’s more fun than it sounds . . . literally.

I was introduced to the idea of a “lark journal” a couple of years ago and loved it. Lark is an old-fashioned word for fun. And a Lark Journal is a notebook (you can buy a small, basic one for a few dollars from pretty much any grocery store) you use only to keep the highlights from various outing and times together. Next time you spend a day together, go out to dinner, etc., take a few extra minutes to write each of your favorite parts of the day or night.

The fun yet difficult part is trying to not read each other’s entries right away. Instead, hang on to them for a particularly cold, dark day, and bring the journal out when you’re not sure what else to do together or need some cheering up from the winter blues. It is a beautiful way to recall some of the special times you’ve had together, and can come in handy when things get tough or you’re stuck in a rut.

Sharing dreams is one of the most beautiful parts of getting to know someone.

It is really cool to experience things this way (including yourself) from your loved one’s perspective, and it’s a good exercise in gratitude.

2. Have a coffee shop day

The point of winter is that not all the time has to be “busy.” Yes, excursions and activities are fun and good, but so is just sitting in a coffee shop.

Whether it’s an old favorite or a recently-opened one that you’ve been wanting to try, you can bring your favorite books, your journals, or a crossword puzzle and spend a few hours in a cozy coffee shop enjoying each other’s company without necessarily doing something together.

This time together—while still intentional—allows for a more “realistic” or full picture of what a relationship can look like over the course of a lifetime (it’s not all movie and dinner dates, people).

And don’t forget to espresso your love for each other!

. . . Too much?

1,000,000 bonus points if you don’t take out your phone or computer during this time!

3. A film festival for two

Choose a classic movie to watch together. Nothing Marvel and no chick-flicks. There are many beautiful, enriching films out there that will inspire you, give you some important perspective, and encourage meaningful conversation.

Treat it like a true movie night. Popcorn, hot chocolate . . . and no texting during the movie, please.

Some excellent, influential movies you and your loved one can enjoy on a cozy night in are:

  • Gone with the Wind
  • Casablanca
  • Psycho
  • Schindler’s List
  • Modern Times
  • The Wizard of Oz
  • Citizen Kane
  • Bonnie and Clyde

4. Practice your prose

Poetry can be daunting and potentially boring. The reality is that there are a lot of really beautiful poems out there that will inspire us with their beauty—and it can be a good literary exercise for us to decipher them.

Dating is so much more than jumping from one activity to the next. It’s a continual unveiling of the other.

Grab a blanket and some coffee and maybe turn on some classical music—or something jazzy. Start with something simple (see below) and take turns reading it out loud. Take a stab at analyzing it together. You may be surprised as you each give your own interpretation of the piece. Understanding a poem can be hard work, but it allows you to learn patience and can teach you how to problem solve together—while also taking off the pressure that one of you needs to be “right.”

If poetry feels too foreign, try a short story. The point is to take part in a form of entertainment that is slightly more active than merely watching a show or a movie. Furthermore, attempting to decipher the meaning and morals behind these types of works can be another starting point for meaningful conversations and growing in understanding of each other.

Simple and short poems for beginners:

5. Test your teamwork

Puzzles are so cozy and fun. This is something you can easily do with another couple and that provides a low-pressure environment to host. My parents are notorious for turning down dinner invitations in order to stay in and finish the puzzle they had started. You can turn on some music (nothing too upbeat), have a snack or two, and pour some wine. Boom! Fun date night in—plus the incredible feeling of accomplishment when it’s all finished.

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6. Cards ’n’ Kegs

Choose a low-key brewery in your area. Show up with a deck of cards, and play a round or two of some games for two while sipping on your favorite craft beer. This is another one you could make into a double date. And if you’re not a fan of cards, you can also try Scrabble or Checkers!

Some fun card games for two you can try:

If all else fails, have another beer and use the cards to build a tower instead.

7. Go on a dream date

Sharing dreams is one of the most beautiful parts of getting to know someone. Whether it’s together or individually, it’s good for you to have dreams and to know what your loved one is hoping to achieve in life. Set aside an evening or afternoon to write down and read aloud some dreams you would each like to see come true. You can start with some common areas: finance, physical wellbeing, travel, career . . . you could even challenge each other to pick one that you begin working toward today—this way you have some built-in accountability as well.

There is a lot of good that can come out of these dreary days. Be present to each other and get to know our loved one in an intentional way.

BONUS: 8. Channel your inner fancy man (or woman)

Take advantage of this chilly time of year to check out some of the indoor attractions in your town or a nearby city. If you’re visiting an art museum, go the extra mile and dress up to feel more sophisticated (ooh la la). Go to a local library or bookstore and pick out a book you would like the other to read (can you tell I’m a bookworm?). Choose a country and make a traditional meal from there—you could keep the theme going and watch a foreign film from the same country!


Don’t let the winter months pass you by. There is a lot of good that can come out of these dreary days. Most importantly, it gives us the opportunity to be present to each other and get to know our loved one in an intentional way.

Dating is so much more than jumping from one activity to the next. It’s a continual unveiling of the other—something that requires slowing down and a lot of patience, especially when circumstances (ex: weather) aren’t ideal.

For so long we had something to look forward to. Even though December 25 has come and gone, it doesn’t mean we don’t have anything else to look forward to until spring.

Suggest one of these ideas to your loved one and enjoy this time of getting to know each other just a little better—and love them just a little more every (dreary) day.

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