Saturday, September 17, 2016

Old Fashioned Date Filled Oatmeal Cookies

This recipe has special meaning to me. It is the last recipe I got from our Aunt before she unexpectedly passed away. It is a recipe that our mom and our aunt's grandma used to make for them growing up. It does have "old fashioned" written all over it. 
Almost a date square in cookie form, if you will. 
The hint of orange is subtle but really elevates these simple cookies to another level.
When I make these now I always think of our aunt. I hope you give them a try and let us know what you think.

Old Fashioned Date Filled Oatmeal Cookies 

Date Filling
1 lb chopped dates
1 cup cold water
4 Tbsp brown sugar
4 Tbsp orange juice
2 tsp lemon juice
grated rind of 1/2 an orange

1 cup butter, room temp
1 cup brown sugar
2 cups rolled oats (not quick oats)
2 cups flour
1 tsp baking soda
pinch salt
1/4 cup boiling water
1 tsp vanilla

Prepare date filling - In a medium saucepan, combine dates, cold water, brown sugar, orange juice, lemon juice, and orange rind. 

Cook over medium heat, stirring often, until thick and smooth. Remove from heat and let cool while you make cookies.
Prepare cookies - Line a cookie sheet with parchment paper. Set aside. 
Preheat oven to 375.
In a large mixing bowl, beat butter and sugar until smooth, scraping sides of bowl as needed. Stir in rolled oats. Next, stir in flour, baking soda, and salt. 
Add in the boiling water and vanilla and stir until well combined. Dough will be crumbly but stick together when you press it in your hand. 

Scoop onto prepared cookie sheet and press with a fork (or the palm of your hand) to flatten slightly.

Bake at 375 until lightly golden brown, about 10 - 15 minutes. Remove from heat and let cool on cookie sheet for about 5 - 8 minutes before removing to wire rack to cool completely. 

When cool you can sandwich the cookies together with the cooled date filling.
Flip over half of the cookies so the bottom is facing up.
Scoop a generous amount of date filling onto the flipped cookies.

Top with another cookie - bottom of that cookie facing down to touch the filling. Gently squish them together. 

Continue until all the cookie are used up.

You can make them as small or as big as you like, just keep in mind that with that lovely date center they are very rich and filling.
I believe I used my medium cookie scoop and got approx 23 or 24 cookies - which means 11 or 12 fairly large sandwich cookies. 

These freeze well too, FYI.
Also, if you want even more orange flavor simply grate the rind of a whole orange instead of just half. 
Our mom loves these as she says they remind her of her grandmother (plus they taste fantastic). 
I love them because they remind my of our aunt (plus they taste fantastic). 


  1. Thank you for sharing this. I really like dates, and cannot wait to try this recipe. The first thing that came to mind was the (also old-fashioned) date pinwheel cookies that my mom used to make. I've never enjoyed the process, but I'm thinking these would combine all the flavors we like without the hassle of rolling the dough!

  2. Thank you thank you thank you! I have almost spur of the moment company coming tomorrow and I didn't have a thing in the house - I went to trusty Pinterest and happened upon this recipe. My grandmother used to make these for us and we loved them! Being short on time with a house to clean still I remembered the box of oatmeal cookies sitting in the cupboard that hadn't been opened and used them for a shortcut. They worked out wonderfully! The filling is exactly what my grandmother did as well - most recipes don't seem to call for it and its such a great addition. Will be using this recipe alot :)

    1. *don't seem to call for orange juice. Sorry its rather late and I think I'm about ready for bed once the filling cools down enough in the cookies to pack away til tomorrow lol

  3. My mom used to make something similar but only at Christmas. She rolled out the cookie dough fairly thin and cut them with assorted cutters and then filled them with date filling. Everybody loved them and misses them since she passed.

    1. They would make a perfect Christmas cookie :)
      Thank you for sharing your memory with us.

  4. My Gramma used to make date filled cookies similar to these. They freeze really well and my best memories from childhood include sneaking into the freezer for a frozen date filled cookie and eating it before it was completely thawed.

  5. Saw your picture and those were my dads fav cookie. Mum used to make them often... oh how I miss themboth. I make them sometimes and the kids say grampas fav and yes my kids are

  6. I never had a grandma that made these cookies, but I just might be a grandma that makes these cookies one day! LOL they are my husband's new favorite, and mine too. The only thing that I did differently was I browned the butter. Love this recipe! Thanks, Holly