12 Dates of Christmas

A fun, memorable way to spend the holiday season with your partner. I created this back in 2016 and my husband and I still talk about it because we loved it so much.

Back when my husband and I were dating, I wanted to do something cute for him without being too cutesy. You know, cute to me and other women, but not so cute that other dudes would make fun of him if they found out about it (eyeroll).

I got the idea from watching a Christmas chick flick called (drumroll)…12 Dates of Christmas, starring Amy Smart and Mark-Paul Gosselaar.

The movie actually has very little to do with going on 12 dates (in the movie they actually repeat the same first date 12 times, sort of), but I thought it was such a catchy title and then thought, “hey…that would actually be kind of cool.”

I’m sharing this idea with all of you eight years after the fact because it just popped up in my photo memories and it’s too good to keep to myself. This was one of the best ideas I have ever pulled off because it was so fun and memorable.

You could easily use this as a month-long Christmas present instead of gifting “things.” It’s time well spent together and you can make it as expensive or inexpensive as you want–truly. I’m going to break it all down for you here and tell you how to pull it off in five simple steps.

Let’s dive in.

Step 1: Planning

After inspiration struck, my brain went crazy coming up with all kinds of things we could do together and how I could put it all together and pull it off. I quickly realized that in order to truly make it 12 dates of Christmas, I would have to cram 12 dates into 24 (or 25) days, which breaks down to basically every other day to fit it all in.

This is not necessarily easy. Working around work schedules and other functions around the holidays makes for an extra challenge. If you have kids, that’s even harder. If you have kids that also have activities…even harder yet. But it’s not impossible and, if you wanted to, you could even make this a family thing instead of just dates for you and your partner. We didn’t have kids or (many) obligations when I did this eight years ago, so we just had some tired days after some later nights.

To start, I suggest pulling out your calendar and writing down every single thing happening from December 1st to December 25th that you are currently aware of so you can figure out when you both (or all) have free time to partake in each date.

Be specific. Write down all of it so you know when you actually have the time free. And keep in mind that you don’t necessarily need entire evenings or hours upon hours to complete activities. An hour here or there can definitely work too.

Step 2: Budget + Schedule

If you need or want to, set a budget first before you go crazy planning things you can’t actually afford to do. If you should be looking at free events instead of front row center tickets to the Nutcracker, then by all means…stay in that lane. Don’t disappoint yourself by dangling expensive events or activities knowing you won’t be participating.

I ended up doing a couple of bigger, more expensive things and the rest were free or very inexpensive. For example, one of our favorite country artists happened to be coming to our area early December that year, so I got tickets for us to go. Not exactly holiday themed, but it was still fun and something we got to do together.

For the remaining days, we went to holiday themed events, gave back to our community, and had a couple fun at-home nights where we did something holiday themed.

Here’s exactly what we did for each of the 12 Dates:

Concert (Cole Swindell)
Holiday themed market (Holidazzle, back when it was at Loring Park in Minneapolis)
Attended our city’s annual Christmas tree lighting
Rang bells for Salvation Army red kettle at our local grocery store
Saw the Canadian Pacific Holiday Train stop in a nearby city
U of M Arboretum Winter Lights exhibit
Drove around neighborhoods to see Christmas light displays
Holiday painting class at our local bowling alley
Made popcorn and festive holiday cocktails at home and watched our favorite Christmas movies
St. Paul Santa Crawl + Trans-Siberian Orchestra concert
Dinner at a new-to-us restaurant
Movie theater night

To go with each date, I had a small wrapped “gift” that was a clue as to what our date was going to be. I usually gave it to him the day of or right before, depending on timing of things.

For example, when we went to see Cole Swindell, I bought his latest CD (they were still around back in 2016) and had him open it before we left and we listened to it on the way to the venue. For the CP holiday train date, I bought The Polar Express book and wrote in the front of it as a keepsake. For the annual Christmas tree lighting, I wrapped up an ornament that we brought with to the tree lighting and hung on the tree. For our painting class, I wrapped up a cheap pack of children’s paintbrushes.

Step 3: Brainstorm

Next, think of things you want to do or you think would be fun to do together during this holiday season. Here’s some holiday themed suggestions:

Construct a gingerbread house, candy train, or other holiday themed confection.
Bake cookies
Volunteer for a charity event, food shelf, toy drive, church, school, or other “give back” activity
Ice skating, sledding, tubing, snow shoeing, or other outdoor winter activity
Decorate a Christmas tree, indoors or outdoors
Go caroling
See a play or concert
Holiday shows, plays, exhibits or events
Make your own Christmas cocktails or find a place serving festive drinks
Watch a holiday movie
Take a class with a holiday theme i.e., painting, sign making, flower/plant arranging, cooking, etc.
Community events i.e., tree lightings, parades, bonfires, etc.
Christmas shopping for yourselves, others, or to donate to charity
Do a workout together wearing Santa hats
Make Christmas cards for friends and family
Take festive holiday photos as a keepsake or to share with family and friends
Sexy time with a holiday theme (if you just started to sweat or got embarrassed, I apologize. I definitely blushed even typing this one, but I also think it’s a great idea…so take it or leave it).
Learn something new together i.e., knitting, woodworking, karate, hot yoga, a new exotic recipe, dance routine, couples challenge (Google it, you won’t be disappointed), etc.
Game night with Christmas cookies and cocoa

The sky is the limit, honestly. You can do almost anything and add some red + green to it to make it feel holiday themed. Don’t limit yourself to just “holiday” activities.

The best part about this is that you are designing it with you and your partner or family in mind. Choose things that you think would be fun but also a little out of your comfort zone for some new experiences. Jaremy and I had never painted anything but walls when we took the holiday painting class and it was one of our favorite things to do (even though neither of us has a natural talent for it). It’s all about time spent together and making memories. I guarantee that planning this all out will be talked about for years to come no matter what it is that you decide to do for each of the 12 dates.

Step 4: Put Your Plan into Action

Now that you’ve done your research and planned your dates, it’s time to execute your plan.

Right away, secure any tickets you need to buy. Make the reservations for restaurants or classes so they aren’t full. Don’t wing it. You want this to go as flawlessly as possible so you are also having fun and not sweating the details as you go.

Go through each date in your head from start to finish. Some of them will have a couple layers of planning. For example, for the CP holiday train, I needed the clue, but also made sure we had a food shelf donation to bring with (it’s a free event but they ask you to make a donation). For anything with a venue, it’s a good idea to choose parking ahead of time if there isn’t on-site parking.

For the clues, I went and got everything I wanted to use all in one afternoon shopping trip. Then I went home, wrapped them all, labeled them with each date number 1-12, and put them in a basket on our kitchen table so I wouldn’t forget about them and to build anticipation.

For the first date, I also got a Christmas card and wrote a note about what would be occurring over the course of the next 25 days, for 12 dates, explaining the idea and that each date would have a clue before we participated, and expressing my hope that this would be nostalgic for us in later years and something we could look back on fondly (awwwww).

Step 5: Have a Backup Plan

Just in case any of your original date ideas fail, or something happens that inhibits you from getting to partake (weather, event cancellations, illness, etc.), have a backup plan ready.

I had two ideas ready as backups if any of my ideas fell through–and one totally did–so I was happy to have a backup plan without having to feel too flustered or have the entire evening energy ruined.

12 dates of Christmas is one of the most memorable Christmas seasons we have had together. Now that we have a toddler, I’m thinking of bringing it back next year as a family event for a chance for all of us to spend quality time together and make some new holiday memories. If you do this, don’t forget to take pictures! I made a sort of memory book on social media with all of our photos, and you could even make one on an app and have it printed so you can pull it out each Christmas for years to come.

Cheers to spending quality time with the ones we love this holiday season!