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 surely 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 Cookie Recipe

What are old-fashioned date-filled cookies? 

Old-fashioned date-filled cookies are a nostalgic, soft sandwich cookie featuring two rounds of tender sugar cookie dough with a sweet, homemade date jam filling in the center. This vintage 1930s recipe is a traditional holiday favorite, prized for its soft texture and the perfect balance of buttery dough and naturally sweet dates.

Prep time: 20 minutes

Baking time: 10-12 minutes

Key Ingredients: Dates, sugar, flour, and shortening (for that authentic vintage crumb).

Jump to Recipe

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.

Cream: 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, and 2 cups water.

Cook together until smooth and thick.  Roll cookies thin.  Cut out and place on a 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.

Why You’ll Love This Vintage Date Cookie Recipe

If you are looking for the exact date-filled cookies your grandmother used to make, this is the one. Unlike modern recipes that can be too crunchy, this version stays soft and chewy for days.

The Filling is the Star: By simmering the dates with a little water and sugar, we create a thick, spreadable jam that won't leak out in the oven.

Perfectly Balanced Sweetness: The dough itself isn't overly sweet, which allows the rich, caramel-like flavor of the dates to shine.

Make-Ahead Friendly: These cookies actually taste better on day two, after the moisture from the filling softens the cookie even further.

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! 

Tips for Successful Date-Filled Cookies

For holiday cookies, start with a 2-inch 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.

Three Ways to Shape Date-Filled Cookies

While my Grandma always made these as a classic "sandwich" cookie, there are several ways you can shape this dough depending on the look you want or how much time you have. No matter which method you choose, the key is to keep the dough chilled so it's easy to handle!

1. The Classic Sandwich Method (As Pictured)

This is the traditional way to make old-fashioned date cookies.

How to do it: Roll your chilled dough to 1/8-inch thickness on a floured surface. Use a 2.5-inch round cookie cutter to cut out your circles. Place half of the circles on your prepared baking sheet, add a teaspoon of date filling to the center, and top with a second dough circle.

Pro Tip: Gently press the edges with your fingers or a fork to seal the "sandwich" so the filling stays tucked inside during baking.

2. The Fold-Over Crescent (The "Turnover" Style)

If you want a higher dough-to-filling ratio, the crescent fold is a popular vintage variation.

How to do it: Cut your dough into 3-inch circles. Place a teaspoon of filling slightly off-center. Fold the dough over to create a half-moon shape (like a mini empanada or turnover).

Pro Tip: Use a fork to crimp the curved edge. This method is great because it ensures the filling never leaks out of the sides, and it gives the cookies a beautiful, rustic look.

3. The Easy "Drop and Press" Method

Don't have time to roll and cut dough? This is the "lazy cook's secret" for a faster batch.

How to do it: Scoop a tablespoon of dough and roll it into a ball. Place it on the cookie sheet and use your thumb or the back of a spoon to create a deep well (like a thumbprint cookie). Fill the well with the date mixture. You can either leave them open-faced or top them with a smaller "cap" of flattened dough.

Pro Tip: If the dough is sticking to your hands, lightly flour your palms before rolling the balls.

Watch Me Make Cookies with Date Filling for More Tips

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Frequently Asked Questions: Date Filled Cookies

Can I use Medjool dates instead of regular Deglet Noor dates?

Yes, you can use Medjool dates. They are larger, sweeter, and softer than regular dates. If you use Medjool, you may need to reduce the added sugar in the filling slightly and simmer them for a few minutes less, as they break down much faster into a jam-like consistency.

Why does the recipe call for shortening instead of butter?

My grandma used shortening because it was the standard for 1930s vintage baking. Shortening has a higher melting point than butter, which results in a cookie that is taller and softer. Using shortening ensures the dough holds its shape around the filling without spreading too thin or getting crispy.  I always use shortening, too, for authenticity.

How do I store date-filled cookies to keep them soft?

Store these cookies in an airtight container at room temperature for up to 5 days. These are unique because they actually soften over time as the moisture from the date filling seeps into the cookie dough. If you need to store them longer, they freeze beautifully in a freezer-safe bag for up to 3 months.

My dough is too sticky to roll out. What should I do?

Sticky dough is usually caused by the dough getting too warm. Wrap your dough in plastic wrap and chill it in the refrigerator for at least one hour (or even overnight). If it’s still tacky, lightly flour your rolling pin and your work surface. Avoid adding too much extra flour to the dough itself, as this can make the cookies tough.

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

dessert

American

Yield: 48

Author: Donna Urso

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.

Ingredients

The Cookies

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

The Date Filling

• 8 ounces pitted dates, chopped
• 1/3 cups granulated sugar
• 1 tablespoons flour
• 1 cups water

Instructions

To Prepare the Filling

1. Chop the dates. A sharp knife should do it. Alternatively, 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 of 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 of the 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 a golden brown color. Don't overbake.
7. 3-inch cookies will take approximately 20 minutes to bake, and smaller cookies will take 12-15 minutes.
8. Remove to a rack to cool completely.

Notes

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

Calories

140.89

Fat (grams)

4.73

Sat. Fat (grams)

1.87

Carbs (grams)

22.51

Fiber (grams)

0.47

Net carbs

22.04

Sugar (grams)

10.39

Protein (grams)

2.06

Sodium (milligrams)

93.15

Cholesterol (grams)

10.55

Nutrional information is approximate.

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