My Christmas Cookie Box Bloopers

Back in November 2024, I had this phenomenal idea that for Christmas 2025, I would make Christmas cookie boxes for my friends and family. It was sweet.

I tried to hold on to that.

I certainly had fun making my Christmas cookie boxes this year, but the more accurate word to describe my cookie-making experience is definitely humbling. If you’ve ever heard me say someone needs to get me on a baking show, I’d like to formally retract that statement. At least until next year.

People say baking is a science, and I am here to tell you that I really didn’t want that to be true—but it is. I feel like I went into this Christmas cookie box project totally blind. I didn’t have a stand mixer while making these cookies (I literally got one the day I delivered the cookies, though, so my baking game is about to improve greatly), I didn’t have a cooking scale, and I didn’t have a cookie scoop.

What did I have, you may be wondering? An irrational sense of confidence that I could do this thing. And I did, in fact, do this thing. Just maybe not particularly well.

My journey began last Sunday, when I pulled out my notebook and made a cookie-prepping schedule. Here’s the basic math of my cookie boxes: I planned to hand out about 8 boxes with a dozen cookies in each box. I made 6 different types of cookies, with a plan for everyone to get 2 of each type in their boxes, and thus I needed batches of at least 16 for this all to work out. Now, I have two writing degrees, so it was incredibly difficult for me to figure out that math. Nonetheless, I persisted.

The Prep: Thursday

Thursday was day one of Christmas cookie prep. That evening, I prepped the sugar cookie dough and the dough for my raspberry thumbprints. Though I’d made two successful batches of thumbprints earlier in the week (more on that later), I decided to switch up my recipe for the cookie boxes.1

Some of the mishaps were small. My sugar cookie dough ended up with a 17 cookie yield rather than the recipe’s 20, which made me feel like I did something wrong (insert the need for a cookie scoop here). And an issue I stumbled upon frequently during my cookie-making experience is that no matter how closely I followed the recipe, my dough just was not scoopable. It was too sticky to roll into balls by hand, even after I refrigerated it overnight. This was frustrating.2

The Prep: Friday

On Friday, I woke up and immediately baked my sugar cookies. As a side note, let me say: For the past four days, I’ve been eating, breathing, and dreaming about my Christmas cookies. My heart, mind, and soul have been dedicated to completing these cookie boxes. It has been no small feat. So, I woke up on Friday and needed to bake the first batch more than I needed to make coffee (which, if you know me, is saying a lot).

In my frenzy to get the first cookie baked off, I put way too many pieces of dough on one baking tray,3 and the batter spread under the oven’s heat. Now, this happened to me a hell of a lot during this baking process. Every single one of my cookies spread in the oven, no matter how long I froze or refrigerated the dough for. Every time it happened, I felt deflated and like I was failing. And it all started with my first!!! cookie. It was not, in fact, a hot start.

Thankfully, the sugar cookies were easily saved. It was just a little something to take the edge off, if you will; by that I mean my sugar cookies literally did not have round edges. They were sort of like sugar rectangles. Tasty sugar rectangles.

On Friday evening, I prepped three more cookies: snowballs, crunchy chocolate shortbread, and chocolate crinkle.

Maybe it’s because I love all things chocolate, but my chocolate cookie batters came out delicious. The chocolate crinkle cookie was rich and decadent, and those baked up the best out of the six types of cookies I made. I considered keeping the 18 crinkle cookies for myself. I used my favorite baker’s recipe.

The crunchy chocolate shortbread is a recipe I have made before from Alison Roman’s Sweet Enough cookbook (love btw), and I don’t know if my baking skills have actually regressed since I last made the recipe, but something went very wrong. The cookies were not crunchy, nor were they shortbread. They spread in the oven (I could not catch a break, let me tell you), and I ended up calling them “cookie dough bark” because they were soft and oddly misshaped, though still yummy. This might have been my most disappointing fail of the night. I remember really loving the chocolate shortbread when I made it last year, and I was looking forward to having it in all its crunchy glory again. Alas.

My favorite fail story from this Christmas cookie project happened while I was making the snowballs. The recipe I used was from Food Network, and it was fine enough, though a qualm I have is that the recipe calls for putting the nuts in a food processor until they’re “very finely ground,” and I don’t agree. I used pecans for my snowballs, and I think it would have been significantly better if some of the crunch from the pecan was still there when you bit into the cookie rather than incorporating some sort of pecan dust into the dough. But overall, the recipe was fine.

What wasn’t fine was my ability to hold on to a parcel of thought for more than fifteen minutes. At the beginning of the recipe, I decided I was going to half it, because the recipe yield was four dozen cookies, and that was way more than I needed. Because I can’t remember a thing to save my life, though, by the time I was rolling the dough, I realized that I forgot I halfed the recipe, so I ended up putting the normal amount of flour in a bowl with ingredients that I’d halfed at the beginning.4 As a result, my first batch of snowballs were dense and slightly chalky.

I made a second batch and found the dough much more rollable than the difficult-to-knead first batch. I set them in the fridge for a good night’s rest, and at around 11 p.m., as I was watching Friday Night Lights, a pang of fear hit my chest as I realized the most mortifying thing: I forgot to put sugar in the second batch of snowballs.5 I forgot sugar. In a cookie recipe.

Thankfully, the recipe called for powdered sugar, so I rushed to the kitchen, took my snowballs out of the fridge, and spent the next fifteen minutes pushing teaspoon-sized amounts of powdered sugar into the center of each cookie ball, then re-rolling, then placing them back on the parchment paper tray to go into their frosted sleep. I went to bed defeated.

The Prep: Saturday

Saturday morning was a baking morning. At 8 a.m., I baked my snowballs and rolled them in powdered sugar (once when they were fresh out of the oven and once again when they were cooled). I rolled my crinkle cookie dough in granulated and powdered sugar pre-bake, and those (as I mentioned before) came out beautiful. I also baked my thumbprints, and, to literally no one’s surprise, the dough spread. I hadn’t even had my coffee yet, and I’d already had my first fail of the day—later that morning, my shortbread spread in the oven, too. Let’s just move on.

In the evening, I prepared what I would say was my second success story of this Christmas cookie baking process: my gingies! Otherwise known as gingerbread cookies. I used a recipe my friend Shelby had tested the night before, and it did not disappoint.

The Prep: Sunday

The gingies baked up perfectly—they were soft in the center, crunchy along the edges, and I decorated them to the best of my ability (which is minimal). There were Christmas trees, gingerbread men, Santas, and even mittens! I iced some, left some of the cookies plain, and dusted others in just powdered sugar. The gingies were the only recipe where I got a higher yield than I expected, so I threw a little extra in each box for good measure. It’s Christmas, after all.

The Assembly

The final step was assembling the cookie boxes, which brought me full circle, back to the math part of this project. My brain hurts.

I ended up with seven cookie boxes, each with anywhere from 12 to 14 cookies, depending on how much I like the recipient—I’m kidding. I gave a few people extras of cookies I knew they’d like the most, because I pay attention to my friends and family, duh.

And thus, on this snowy Sunday, I hopped in my sleigh6 and delivered my Christmas cookie boxes to my friends and family.

My Takeaways

If you’re considering an undertaking of this magnitude and it’s your first time doing it, my note to you is this: Lower your expectations. These cookies were not my best, and that’s okay. It was my first time making this many cookies (over one hundred!) and it was bound to be a learning experience. Next year will be better. I will have a cookie scoop. And a scale. And a stand mixer. And more humility.

Even more about cookies, and other stuff:

• Sarah Fennel is my favorite baker, and I attended her Christmas cookie swap in NYC earlier in the week, which was an epic experience. I also got to take a photo with her and we chatted about my food Substack, which all started because I love her blog so much.

• I made coconut caramel thumbprints (from Sarah Fennel’s Sweet Tooth) and chocolate chip peppermint cookies for a cookie swap I did with my lovely friend Shelby, who’s also a Substacker. Shelby made me espresso martini cookies, the aforementioned gingerbreads, and oatmeal raisins. I went over to her apartment and we watched Julie & Julia, which is my new favorite movie. I love Christmas cookie season.

  • I’ll note that my chocolate chip peppermint cookie dough also spread in the oven. I ended up with one big chocolate peppermint cookie pancake, and my festive cookie cutters saved the day.

• I got an immersion blender at my work holiday party gift exchange, so I’ll be knee-deep in soup once Christmas cookie season is over. Send recipe recommendations!

• Had some meals/bevs worth mentioning: Tara Mor (W 30th Street), Bar Primi (I went to the Bowery location, but there are multiple), and a divine matcha from The Lark (Church Avenue).