I started with what I thought would be the easiest cookie to put together, given that I’ve made sugar cookies hundreds of times before. I chose this simple recipe and followed standard cookie baking protocol: I whipped up some buttery dough, let it chill for a couple of hours, then rolled it out for cutting. Everything went as anticipated, and I was feeling all Martha Stewart-like when I took the cookies out of the oven. Perfectly shaped, not burnt, and ready to get all presentable.

Then came the decorating. In order to save time, I opted for store-bought icing tubes that seemed ideal for decorating. Big mistake. As soon as I began to ice the cookies, which were cooled down, the icing melted off as if the cookies were bleeding or crying. I didn’t panic just yet; I thought I could hide the mess if I were to dump a bunch of cheery sugar crystals on top. But, to my horror, the crystals started to melt into the icing. I felt cheated for purchasing what I thought would be fail-safe icing, and even more duped for the sugar crystals that didn’t even stay crystallized.

After a handful of really sorry-looking cookies, ones that could be easily mistaken for cookies my 2 year old decorated, I gave up and went for a simple glaze. Some ended up looking OK, considering the huge Pinterest-fail the in the beginning.

Verdict: Definitely overestimated my icing skills, and I was less than pleased with how some of the cookies turned out. These deceiving sugar cookies left me feeling a little less confident about my baking skills. At least they tasted better than they looked.

I’ve never made these candy cane cookies before, but the dough was quite similar to the sugar cookies, so I thought I’d give it a shot since I had all the ingredients. The goal was to gingerly twist the two dough colors carefully to resemble the look and shape of a candy cane. I was nervous when I first started making the canes for fear that the dough would be too stubborn and sticky and wouldn't form the perfect cane shape, but to my surprise, it wasn’t too difficult. It just took a slow and careful hand to roll out the dough, twist them into the “J” shape (in honor of my daughter's name), and place them onto the cookie sheet.

After taking a good 20 minutes to make an entire cookie sheet of these suckers, I looked over at the two balls of dough and realized that I had only used a third of the dough and had a long way to go. But making the canes was oddly therapeutic, so I didn't even mind that I was about to make 50 candy cane cookies. Plus, look at how cool they look when they come out of the oven!

Verdict: Time consuming, but surprisingly more simple to make than I originally anticipated! And super, super cute! I felt much better about my baking skills after this because of how photogenic and tasty they turned out, and I moved forward with the confidence of a Pinterest queen.

When I think of Christmas, one of the first baked goods that pop into my head is the gingerbread man. They have such a distinctly special taste, perhaps precisely because of the spicy ginger, so I couldn't go through the holiday season without making them. However, be warned: the molasses is also what makes the dough exceptionally sticky. I was very generous with my “sprinkle” of flour — I dumped handfuls at a time to completely cover my dough — and worked with great speed to roll out the dough and cut out the cookies. I'll admit, I started to break a sweat doing this, but I wasn't the least bit worried because my previous cookie making experience taught me to keep my cool and keep going. Speed, focus, and experience paid off because I ended up with some perfectly shaped gingerbread men. They baked to perfection in just 10 minutes.

Then came the frustrating part. Determined to avoid the melting icing disaster I went through with the sugar cookies, I refrigerated the icing right before decorating to harden up the consistency because I thought the icing might have been too runny since it was warm (I live in Southern California where we wear tank tops some days in December). It seemed like a logical fix to me, kind of like how chocolate melts in the heat and hardens when cooled, but I was terribly, terribly wrong. Turns out refrigerating the icing didn’t help one bit, and the icing was just as runny and completely unmanageable. My poor gingerbread people looked like they fell into a volcano. I was frustrated, to say the least, and sad that some perfectly good gingerbread men were ruined by such awful icing.

More than half of these guys (and gals) were victims of the Second Great Icing Explosion. I spent a good hour cursing at these over-priced tubes of icing that would not stop sputtering goops of green and red everywhere, and I actually felt sorry for the poor little gingerbread people (as if they were real creatures at the whim of my experimentation screaming for mercy) that had no face, or just one eyeball. But I did manage to put on some smiles and buttons on a handful of them!

I mean, some of them look happy ... right?

Verdict: Despite my failed attempts to give these gingerbread people some happy faces and pants, my partner and toddler gobbled them up with no reservations. I was relieved that my family couldn't care less about the gingerbread men's melted faces and glad that at the end of the day, at least all the cookies would be consumed, which is the most important thing to me. But can the Pinterest gods tell me this: how the hell do you ice cookies?! Is there a 3D icing printer out there that I am completely unaware of?

Since I’m making more than a single batch of baked holiday goods, I thought it would be a good chance to expand my repertoire to include a new dessert: traditional Jewish rugelach, often consumed around Hanukkah. I’ve only ever had rugelach at restaurants, but it's so delicious, I decided to give it a shot (and give me a much needed me a break from icing). Rugelach are a little more complex than the previous cookies because there are a few more steps that go beyond prepping and chilling the dough.

After I chilled the dough and rolled it out into a near perfect circle, I had to lather on layers of apricot preserve and filling. From there, I carefully cut out the dough into 12 perfect slices. I then rolled up each slice and slowly placed them onto the cookie sheet for baking. Before I could pop them in the oven, I had to chill them, brush on some egg wash, and then sprinkle on some sugar and cinnamon. Sounds like a lot of steps, and I reread the directions a few times over, but I eventually got I the hang of it.

These babies popped out of the oven smelling, looking, and tasting divine. The flaky crusts with a tart hint of cream cheese, the caramelized apricot preserves coating the edges, and the hidden crunch of walnuts all harmonized together in one delectable bite of everything good in this world. I mean, look at these delicious rolls! How could you say no?

Verdict: Though it was my first time making rugelach, they became my instant favorite. I’m not sure whether these fall into the “cookie” or “pastry” category, but regardless of what they are, there’s no way these are sitting on a table untouched. Everyone from my grandmother to my sister-in-law couldn’t stop munching on them. Move over gingerbread men, this is my new winter favorite. Oh, and they’re totally Instagram-able (I couldn’t help myself):

After all this baking, I can confidently say I know how to pick a good recipe and whip up some tasty dough. The decorating, however, is another skill that I am far, far from mastering. Even though I anticipated the sugar and gingerbread cookies to be simple, I overestimated my icing abilities (or store-bought icing discernment?) and botched more cookies than I’m willing to admit.

Although I’ve never attempted to make the candy cane cookies and rugelach before, these batches turned out to be the best looking (and yummiest, in my opinion) despite — or because of — the extra effort it took to make them.

May the Pinterest gods be ever in your favor.

Images: Courtesy of Loreann Talbo (17), whosjo_mama/Instagram, Giphy (1); Amy, Heather Katsoulis, blucolt, stu_spivack/Flickr