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Grandma's Soft and Chewy Date-Filled Cookies

One of the things I can count on as the Thanksgiving and Christmas seasons arrive each year is a feeling of nostalgia. The traditional foods we serve at our family's holiday tables can sure bring out all the feels.

Now that it is officially cookie season, we should kick it off with an old-fashioned homemade date-filled cookie recipe. This is a soft, tender cookie with dates that is a special, nostalgic, family recipe.  

An Old-Fashioned Date Cookies Recipe

An old fashioned date filled cookie from Grandma's recipe file.

This old-fashioned, date-filled cookie was my dad's favorite cookie from his childhood. My dad was born in 1932 so this recipe has been around for quite a while. 

Grandma's Original Recipe

This is my grandma's date filled cookies recipe from the 1930s and 1940s. 

In fact, the way the original recipe was written made me laugh. Like many vintage recipes from the time, this recipe for date-filled cookies was customarily ambiguous.

 2 cups sugar, 1 cup shortening
Add 1 cup milk, 2 eggs, 6 level teaspoons baking powder, 2 teaspoons vanilla, flour enough to roll.
Filling: Stir 2 packages of dates, 2/3 cups sugar, 2 teaspoons flour, 2 cups water.

Cook together until smooth and thick.  Roll cookies thin.  Cut out and place on cookie sheet.  Fill. Cover with a cookie.  Bake at 350 degrees F, 12 to 15 minutes.

I've rewritten the recipe for all of us modern-day cooks, cutting the date filling in half.  I always have too much extra filling when I make as much as the original recipe. I've also added details and hints from my experience making these cookies.

These cookies have all the old-fashioned flavor you want.  This is an official old-fashioned date cookies recipe. My dad confirmed it.

How to Make Date Cookies Like My Grandma

This is a rolled cookie, made from two rounds of cookie dough. 

A deliciously sweet date filling is sandwiched between the two cookies. 

You can make them small and dainty or large and hearty.  Just adjust the cooking time accordingly.

These cookies will be wonderful as holiday cookies and gifts for favorite cookie lovers.  

Don't be too shocked when you go to buy your dates.  They are expensive! 

Two rolled-sugar cookies filled with a delicious date jam.


Tips for Successful Date Filled Cookies

For holiday cookies, start with a 2-inch sized round cookie cutter.  That will make a perfect cookie for holiday cookie platters.

Chop your own dates.  Yes, it will take you a little longer to make your cookies but they will taste better. I find the pre-chopped dates do not make as yummy a filling as when I chop my own dates.

Don't overbake your cookies.  Soft and chewy date cookies are the best.  

Be generous with the filling but be sure to leave enough room to completely seal the top cookie to the bottom cookie.

Watch Me Make Cookies with Date Filling for More Tips

More Old-Fashioned Cookie Recipes

Molasses Cookies are soft cookies perfect with a glass of milk.
Gingersnap Cookies are crisp cookies with a crackled texture. Try making ice cream sandwiches with them.
Iced Oatmeal Cookies take traditional oatmeal cookies to new heights.
Frosted Sugar Cookies have a cake-like texture topped with buttercream frosting.

Grandma's Date Filled Cookies Recipe

grandma's date filled cookies, old-fashioned date cookies, homemade date filled cookies
Yield: 48
Author: Donna Urso
Date-Filled Cookies, An Old Fashioned Recipe

Date-Filled Cookies, An Old Fashioned Recipe

Prep time: 30 MinCook time: 15 MinInactive time: 60 MinTotal time: 1 H & 45 M
A generous-sized cookie with a sweet date filling, made from a vintage family recipe.


The Cookies
The Date Filling


To Prepare the Filling
  1. Chop the dates. A sharp knife should do it. Alternately, use kitchen shears to snip them into the bowl of a food processor. Add one tablespoon of flour to help keep the dates from sticking to the blades of the chopper.
  2. Place the chopped dates and flour (from the food processor if you used it) in a 2-quart saucepan. Add the sugar and water, stir to combine.
  3. Heat the mixture over medium heat and cook until thick, about 15 minutes. Set aside to cool to room temperature.
To Prepare the Cookie Dough
  1. Mix the flour, salt, and baking powder together in a large bowl. Set aside.
  2. In the bowl of your electric mixer, cream together the shortening and the granulated sugar, about 3 minutes, or until light and fluffy.
  3. Add the eggs, one at a time, and the vanilla, beating to combine well.
  4. Alternately add the dry ingredients and the milk, beginning and ending with the flour mixture.
  5. Divide the batter in half, wrap in plastic wrap and refrigerate until ready to use.
Baking the Cookies
  1. Preheat the oven to 350 degrees F.
  2. Lightly flour your rolling surface. Roll out one-half of the dough to a thickness from 1/8-1/4 inch using a rolling pin.
  3. Cut the rounds for your cookies. For HUGE cookies, use a 3-inch round. 2-inch or 2 1/2-inch round cookie cutters will work, too. These cookies expand in the oven, so if you start smaller you'll have more room on your cookie sheet.
  4. Place one cookie on an ungreased baking sheet. Top the cookie with approximately one teaspoon of the cooled date filling. Be generous with the filling, but be sure to leave a border along the edge to seal the top cookie to the bottom cookie.
  5. Then place a second cookie round on top of the first. Press the edge of the top cookie to the edge of the bottom cookie all around. Continue to assemble additional cookies, nine to twelve to a cookie sheet depending on the size cookie you are making. Seal the edges using the tines of a fork dipped in flour.
  6. Bake one pan of cookies at a time on the center rack of your oven. until they start to tinge with golden brown color. Don't overbake.
  7. 3-inch sized cookies will take approximately 20 minutes to bake, smaller cookies will take 12-15 minutes.
  8. Remove to a rack to cool completely.


Make the filling first. It needs to come to room temperature. The cookie dough requires 30-60 minutes of cooling time in your refrigerator.

This is not a quick recipe. It will take you an afternoon.

Nutrition Facts



Fat (grams)


Sat. Fat (grams)


Carbs (grams)


Fiber (grams)


Net carbs


Sugar (grams)


Protein (grams)


Sodium (milligrams)


Cholesterol (grams)


Nutrional information is approximate.

PIN This:
The best old fashioned date-filled cookie from Grandma's recipe box.



  1. Can you use butter instead of the shortening?

    1. You can try but I always make these cookies exactly as the family recipe is written, with shortening.

    2. I'm in my 70's and Date filled cookies originated from my German Grandmother.
      My recipe is similar to original you posted.
      I quit sealing the top cookie to bottom by crimping with fork years ago!
      They are more delicate tasting by putting ample date filling inside and after I top...I simply use my 3 fingers and gently push down on top to spread the filling more evenly.
      The cookies bake and taste so delicate and look fanatical with the 3 finger indentation on top.
      My family absolutely love them!
      My Sister still does fork sealing...I think it makes them too crunchy around the ends.
      Other note on matter how much filling I put stays put on cookie and not run out sides...that I first was afraid of. Marilyn


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