Skip to main content

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 Filled Cookie

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


Post a Comment

Talk to me. I welcome your comments. (These comments are strictly moderated. Spammers take note.)

More Popular Posts

How to Make a Perfect Bacon and Eggs Breakfast

In my opinion, the best breakfast consists of two perfectly fried eggs, crispy bacon, and toast made with hearty bread. This bacon and eggs recipe delivers. It is the breakfast you want when you have time to relax around the kitchen table, drinking a cup of coffee or two. The Best Bacon and Eggs Breakfast (This post contains affiliate links for your shopping convenience.  When you make a purchase using these links you help support this blog.) How to Cook Bacon and Eggs My technique was learned from my mom, by watching her make our family's breakfast over and over again, year after year.  This is a basted eggs recipe which means the eggs are cooked in bacon grease. Cooking eggs in bacon fat is easy and takes just a little practice to perfect. All you really need for a great bacon and eggs breakfast is a good nonstick skillet and a good toaster . If you want to make your own bread for toast, a bread machine like mine  will make that easy as can be. Three

How to Trap and Get Rid of Fruit Flies

What can you do to kill fruit flies?  We've all been there.  Fruit flies in the kitchen.  Fruit flies in the bathroom.  Fruit flies buzzing around everywhere in your home.   It's a frustrating problem that happens to everyone at one time or another.  If you are a fresh fruit and produce lover you certainly know what I mean. How to Kill Fruit Flies with Two Ingredients Those pesky little buggers can often be brought into your home on the vegetables and fruit you buy. There are many solutions offered for fruit fly traps to help you solve your problem.   A quick Amazon search found these products. You can spend your money on one of these solutions or I can save you a whole lot of your hard-earned cash today. My solution is the best.  Here's why: You have the ingredients in your kitchen now.  You need apple cider vinegar and a mild dish liquid . It's a healthy, family-friendly solution. It works quickly because fruit flies are attracted to apple cider vin

How to Turn Store-Bought Potato Salad from Blah to Amazing

Here's a potato salad time-saver for you just in time for summer cookouts. You'll love how you can transform grocery store potato salad so easily no matter whether you are hosting a BBQ or bringing a side dish for a summer barbecue. When you need a quick potato salad, and no time to make one from scratch, that ordinary store-bought potato salad you have in your refrigerator can go from blah to amazing in just a few minutes with just a few ingredients. There's no judgment here. We don't always have the time to make a potato salad from scratch. Sometimes it is just easier to stop by your local grocery store to pick up a container of the store-made potato salad. It's good. It's predictable.  It will do.  All it needs is a little doctoring. How to Make Store-Bought Potato Salad Better Take Your Potato Salad from Blah to AH-Mazing! What should you do if you want that store-bought potato salad to have a little more flavor? You're going to a p

Easy Chicken Parmesan-A Make Ahead Freezer Dinner

Chicken Parmesan is a favorite dinner in the Just One Donna house.  It's also a favorite restaurant menu choice. I like to keep Chicken Parmesan prepared in my freezer for those busy weeknights when we might be tempted to head to a restaurant instead of eating at home.  That way, we'll have a delicious dinner all ready to go into the oven and save money to boot.  What's not to like about that? Freezer Chicken Parmesan for Busy Families This post contains affiliate links.  I receive a small compensation when you shop using these links Easy Freezer Chicken Parmesan for Dinner This Chicken Parmesan recipe is made with everyday ingredients in the spirit of semi-homemade. You may already have the ingredients you need in your pantry.   Chicken Parmesan Ingredients That makes this an easy recipe for any mom or dad to prepare in advance for those busy weeknight dinners. Make a double batch and you'll have a baked Chicken Parmesan dinner for tonight and anoth

Forgotten Pork Chops

Today dawned dark and dreary in my corner of New England.  I woke to a dusting of snow, gray skies, and an ongoing drizzle forecast for the remainder of the day.  It's days like these when you turn to a one-pan, comfort food dinner like this recipe for Forgotten Pork Chops. This recipe is perfect for a dreary winter weeknight or any day you want an easy, hearty meal. One-Pan Pork Chops and Rice (This post contains affiliate links for your convenience.  When you purchase through these links I receive a small compensation.)  Forgotten Pork Chops Truth be told, this recipe came about on a day when I wasn't really in the mood to spend time in the kitchen.  Much like today, it was dreary.  It was pouring rain and we had just sent the last of our guests home from my son's wedding. All I wanted to do was sit with my feet up. I needed an easy pork chop recipe!  This recipe is the result and has been a favorite ever since.  The recipe serves two to four, depending on the n

DIY Cheap and Effective Rug Cleaning

I like to use area rugs to make my home feel warm and inviting.  Area rugs help absorb noise and add pops of color throughout your home.  While regular vacuuming is important, you'll want to deep clean your rugs periodically, especially if you own pets,  Today I want to show you how I clean my area rugs.  It is a cheap and effective rug cleaning method. How to Clean Your Area Rugs (This post contains affiliate links for your convenience ) Cheap and Effective Rug Cleaning This post will focus on cleaning polypropylene rugs like I have in my front entry hall and wool rugs like I have throughout the rooms in my house.  Polypropylene rugs are workhorses and take a beating. That's why polypropylene is a good choice for the entry location. Good quality wool rugs are also workhorses and my preferred choice for my home.  They can be pricey, making them an investment decision for many. In my experience, good-quality wool rugs can also be cleaned using this method.  Just be

Rum Punch for a Party

As the weather warms and you start to think about gathering friends and family for parties and celebrations you'll want to think about signature cocktails. This rum punch cocktail is an ideal cocktail for a large gathering because the flavors are irresistible. Don't you think a warm-weather cocktail should make imagine yourself sitting by the shore on a tropical beach with your toes in the sand? Fruity rum drinks are perfect and rum punch is one of those perfect cocktails.  Cool and fruity, rum punch will make a party! One sip and you'll be transported to the beach. Rum Punch Cocktail (This post contains affiliate links for your shopping convenience.  When you make a purchase using these links you help support this blog.) Rum Punch for a Party! Can you make a rum punch ahead of time?  This rum punch recipe is a make-ahead recipe I use whenever we are having a large group for a summer picnic or barbecue.  Use the recipe below as your baseline and double or tripl

Baked Stuffed Pork Chops

My mom, Gloria, was a terrific home-cook.  Her baked stuffed pork chops with cream of mushroom soup recipe has long been a favorite with our family, especially my sons.   I didn't make it often over the years because it never seemed to turn out as tasty as Mom's always did.  One time when Mom made this dish for me I told her I just couldn't make my stuffed pork chops taste as good as hers always did.  As she recited the recipe I realized I consistently omitted two critical ingredients.   There should have been applesauce in the stuffing and a little white wine in the sauce.  Mom had never told me about these secret ingredients. They make all the difference in the world! Do you think she didn't tell me on purpose?   Baked Pork Chops with Stuffing and Mushroom Gravy Baked Stuffed Pork Chops This stuffed pork chops recipe is

Winter Care for Orchids and African Violets

Are you familiar with the term "hygge"?  It's a Danish term that has caught on in the U.S. because it speaks to the feelings of coziness and relaxation we seek during the winter months.  It emphasizes the simple things in life and the feelings of a life well-lived.   One of the ways I create hygge this time of year is by making sure my collection of African violets and orchids is happy and healthy. How to Care for African Violets and Orchids During Winter This post contains affiliate links.  We receive a small compensation when you shop with these links. Your houseplants are most likely crying out for some attention right now.  If you are like me, you ignored them a bit during the busy holidays.  After all the festive decorations are put away, it's time to give your plants a lovely spa treatment.  Read on for tips on how to care for orchid plants and African violets in winter.