So, you hear “Christmas dating” and you probably think about cozy evenings, maybe some mistletoe, right? Well, my version of “dating” Christmas over the years has been a bit different. It’s been more like an annual appointment with a very demanding client who has a long list of expectations.

My Early Attempts at “Perfect”
I used to go all out. I mean, really all out. I’d start planning in October. Who was coming? What would everyone eat? Did Aunt Mildred still hate cranberries? The gift list was a military operation. Decorations? Had to be Pinterest-worthy, of course. I was trying to orchestrate this perfect, magical Christmas, like the ones you see in old movies.
What did I get? Well, a lot of stress, mostly. You’d think trying to make people happy would be, you know, happy. But it was more like this:
- Coordinating schedules: Like herding cats. Everyone’s busy, someone always has another commitment.
- Food preferences: One’s vegan, one’s gluten-free, one only eats beige food. You end up making five different meals.
- Gift expectations: Trying to find that “perfect” gift that shows you care but doesn’t break the bank, and then someone looks mildly disappointed anyway.
- The pressure: Just this unspoken thing in the air that everything HAS to be magical.
It felt like I was project managing a space launch with a budget of pocket change and a team of volunteers who all had different ideas of what a rocket should look like. One year, I swear, I spent more time making spreadsheets than actually enjoying anything.
The Breaking Point
You’re probably thinking, “Okay, drama queen, it’s just Christmas.” And yeah, I get it. But there was this one year, about a decade ago, that really changed how I “date” the holidays. That was the year I decided we’d have the ultimate family Christmas. The whole shebang. My wife was on board, bless her, but mostly it was my grand vision.
I booked this big rental cabin in the woods. Supposed to be snowy and picturesque. It rained. Non-stop. The “charming rustic fireplace” smoked out the entire ground floor the first night. My brother-in-law, bless his heart, tried to “fix” the Wi-Fi router by unplugging everything and then couldn’t remember how it went back together. So, no internet for three days with a bunch of increasingly grumpy teenagers.

Then the oven in the cabin decided to run about 50 degrees hotter than the dial said. Christmas dinner? Half of it was charcoal. I’d spent weeks planning this menu, sourcing ingredients. I even tried to make a fancy Yule log cake from scratch. It looked less like a log and more like something a dog had been sick on.
But the real kicker? I was so busy trying to make everything perfect, running around like a headless chicken, that I barely spoke to anyone. I was snapping at my wife, stressed about every little detail not going according to my master plan. On Christmas Day, after the burnt dinner fiasco, I just sat on the porch in the rain, feeling like a total failure. My kid, who was about ten at the time, came out and asked if I was okay because I looked “really sad.” That hit me hard. Here I was, trying to create “magic,” and I was miserable and making everyone around me walk on eggshells.
What I Do Now
So, yeah. That was my big Christmas “dating” disaster. What did I learn? I learned that “perfect” is a scam. It doesn’t exist. Now, my approach to Christmas is way different. We still do things, but it’s simpler. Potluck dinners, so everyone chips in. Gifts are smaller, more thoughtful, or sometimes we just agree on no gifts for adults and focus on the kids.
If something goes wrong? Oh well. We laugh about it. The oven breaks? We order pizza. Rains instead of snows? We play board games inside. My “date” with Christmas is now much more relaxed. It’s about actually spending time with people, not about putting on a show. And honestly? It’s a hundred times better. I actually look forward to it now, instead of dreading the workload.