Old Fashioned Date Filled Sugar Cookies

  • 16 ounces pitted dates, chopped
  • 2/3 cups sugar
  • 2 tablespoons flour
  • 2 cups water


  • 2 cups granulated sugar
  • 1 cup shortening
  • 2 large eggs
  • 2 teaspoons vanilla
  • 6 teaspoons baking powder
  • 1 teaspoon kosher salt
  • 1 cup milk
  • 6 cups all-purpose flour


First, make the filling. Chop the dates.  Snip the dates using kitchen shears into the bowl of an electric food chopper.  Add the 2 tablespoons of flour to help keep the dates from sticking to the blades of the chopper. Place the chopped dates in a 2-quart saucepan. Add the sugar and water, stir to combine. Heat the mixture over medium heat and cook until thick, about 15 minutes. Set aside to cool to room temperature.

While the filling is cooling, make the cookie batter. Mix the flour, salt and baking powder together in a large bowl. Set aside. In the bowl of your electric mixer, cream together the shortening and the granulated sugar, about 3 minutes, or until light and fluffy. Add the eggs, one at a time and the vanilla, beating to combine well. Alternately add the dry ingredients and the milk, beginning and ending with the flour mixture.

Divide the batter in half, wrap in plastic and refrigerate until ready to use. Preheat the oven to 350 degrees F. When ready to assemble the cookies, lightly flour your rolling surface. Roll out one-half of the dough to a thickness between 1/8-1/4 inch using a rolling pin. Choose the size of your cookie cutter.  Use a 3 inch round to make HUGE cookies. I recommend a smaller round, about 2 inches. These cookies expand in the oven, so if you start smaller you'll have more room on your cookie sheet.

Place one cookie on the baking sheet. Top the cookie with the cooled date filling. Be generous, but be sure to leave a border along the edge to seal the top cookie to the bottom cookie. Now place a second cookie on top of the filling. Continue to assemble additional cookies, eight or nine to a cookie sheet. Bake one pan of cookies at a time on the center rack of your oven. My large sized cookies took 20 minutes to bake, smaller cookies will take 12-15 minutes. They are done as they start to get a tinge of golden color.

Remove the cookies to a rack to cool. Cool completely.