Date Pinwheel Cookies

I hadn't had a great experience with Date Filled Squares, so I was leery of this recipe for Pinwheel Cookies, which also looked to be filled with dates. However, Passover and Easter were approaching, and we were attempting a Middle Eastern meal to celebrate the season. Since dates are so prevalent and well-loved in that part of the world, these cookies seemed like the perfect dessert. I just had to cross my fingers and hope they were good. But, in case they weren't, I only made half a batch because the original recipe seemed huge. 

How to make Date Pinwheel Cookies

I started with the filling because it needed to cool before it could be used. My dates weren't pitted, so I first took out the pits and then gave them a chop. Next, I put them in a saucepan with 1/4 cup of brown sugar and 1/4 cup of water. 

I turned the heat to medium to cook them. I assumed the dates needed to cook down into a sort of paste, but halfway through the process, I found that I needed more water. I added another 1/4 cup and continued cooking and stirring until the mixture was thick and jammy. 

After the cooked dates had cooled for a few minutes, I added some chopped nuts, then I plopped the mixture into a bowl to let it continue to cool. 

On to the dough. 

One lesson I learned during the Date Filled Square fiasco was that if I was trying to make a flavorful treat, shortening was not my friend. So, the first tweak I made was to swap out the shortening for butter. I creamed that with the sugar, then added the eggs and vanilla.

I was about to add the flour to the creamed mixture, when I noticed that Grandma's recipe says to add half the flour, mix that, and then add more flour, "enough to make a soft dough." You gotta love old-fashioned recipes. 

I'm all about a pinch of this and a pinch of that when I'm cooking, but my baking recipes need to be precise. So, I dumped 1 and 3/4 cups of flour into a sieve, figuring I could add the remaining 1/4 cup if the dough didn't seem rollable.  I added the leavening and the salt and sifted these ingredients in. 

Next, I beat that together. The dough seemed to have plenty of flour without the remaining 1/4 cup. 

I floured my rolling mat, gathered the dough together, and formed it into a rectangle to make it easier to roll into that shape. 

It was then time to add the dates. 

The cooled mixture was quite thick, and I wondered if I would even be able to spread it on out onto delicate dough. The best thing, I decided, was to dollop it all over the rectangle and then spread it out. 

That technique worked pretty well, but you can see that it was thin in some places and thick in others. Adding a little more water to the date mixture might have helped. 

It was too late now, though. I moved on to the next step and rolled the dough up from the long side, jelly-roll-style. 

I trimmed the ends, wrapped it in plastic, and placed it in the fridge to chill.  

The recipe said to chill it for four hours, but I hadn't left that much time in my schedule. I left it in for one hour and that seemed to be plenty. I had no trouble cutting it into slices. 

After I laid the slices onto a parchment-lined cookie sheet, I decided I could have made a better effort at keeping my dough log round. Flat on one side, curved on the other, these slices seemed more like the opening to a tomb. Oh well. That seemed appropriate for our purposes, so I didn't try to change the shape. The baking process somewhat improved their appearance, but I still have work to do to make them look nice.  

The Verdict

I brought them out at the end of our pseudo Middle Eastern meal (which, if you're interested, consisted of shawarma, flat bread, olives, grapes, yellow rice, and hummus.) The family was dutifully impressed by the swirls in the cookies. And then they took a bite. 

Murmurs of appreciation filled the room. Soon, the family was reaching for more.  These cookies were a delicious balance between a tender crumb and a sweet, caramel-like ripple that wasn't super thick, which was one of the problems with Date Filled Squares. The nuts added an additional layer of texture and crunch. As I had hoped, these date-filled bites were the perfect finish to our meal. We topped off the evening by watching the movie The Prince of Egypt.  

I highly recommend all of the above.