“Gramma’s” Old-Fashioned Date Squares (A Chewy & Classic Treat!)

Are you searching for the ultimate, nostalgic comfort-food dessert? The kind of soulful, “from-scratch” treat that tastes just like the one grandma used to make—impossibly chewy, perfectly sweet, and packed with a rich, jammy fruit filling? This incredible, “Gramma’s” Old-Fashioned Date Squares recipe is that perfect, timeless tradition. We’re talking a rich, buttery, and unbelievably tender oatmeal shortbread crust, a luscious, and deeply caramelized homemade date filling, and a final, magnificent, golden-brown streusel crumb topping.

This isn’t just another bar recipe; it’s a guide to mastering a legendary, multi-generational secret. This is pure, old-fashioned baking at its absolute best. We’ll show you the simple but crucial “old-world” secrets to a flawless, foolproof, and unbelievably moist and flavorful bar that will be the star of your holiday cookie platters, bake sales, or a cozy afternoon with a cup of tea.

Table of Contents

Table of Contents

Recipe Overview: The Ultimate “Chewy & Jammy” Holiday Bar

What makes this “Gramma’s” Date Square so spectacularly delicious is its incredible, deep flavor and its wonderful combination of textures. This recipe is a masterpiece of classic, rustic baking. The “magic” of this recipe is the two-in-one oatmeal crumb mixture, which acts as both the sturdy, buttery base and the crunchy, golden-brown streusel topping. The heart and soul of the bar is the from-scratch, cooked date filling. Sweet, pitted dates are simmered with water and brown sugar until they break down into a thick, rich, and jammy paste, which is then brightened with a brilliant, secret splash of lemon juice.

Metric	Time / Level
Total Time	1 hour 30 minutes (includes cooling)
Active Prep Time	25 minutes
Difficulty Level	Easy
Servings	12 squares

The Baker’s Pantry: The Essential Ingredients

This iconic dish uses a handful of high-quality, simple ingredients to create its signature rich and comforting flavor.

• The Oatmeal Crumb (The “Two-in-One” Secret!):
  • Pastry Flour: This is a “Grandma’s secret” to an incredibly tender, “short,” and melt-in-your-mouth texture that you can’t get from all-purpose flour.
  • Rolled Oats: A classic, hearty addition that provides a wonderful, chewy texture and a nutty, wholesome flavor.
  • Brown Sugar & Softened Butter: The classic, rich, and caramel-flavored foundation. Using softened butter (not cold!) is the key that allows this to come together as a crumbly, mix-in-style dough.
• The “Jammy” Date Filling (The Heart of the Bar!):
  • Pitted Dates: The star of the show! Diced, pitted dates (like Medjool or Deglet Noor) are perfect.¹
  • Lemon Juice: The crucial, “secret weapon!” A final splash of fresh lemon juice is the key that cuts through the richness and balances the deep, sugary sweetness of the dates, making the whole bar taste bright and complex, not just sweet.

The Baker’s Masterclass: The Secrets to a Perfect Date Square

This recipe is all about a few simple but brilliant techniques that guarantee a flawless, impressive result.

1. The “Cooked Filling” is KEY!: The number one, non-negotiable secret to a perfect date square that is never dry is to cook the filling first. Simmering the dates, water, and brown sugar on the stovetop is the key that breaks them down into a thick, rich, jammy, and moist paste. This is the secret to that perfect, gooey center that will never dry out in the oven.
2. The “Pastry Flour” Secret: The key to the authentic, old-fashioned, “melt-in-your-mouth” crumb is the pastry flour. Pastry flour has a lower protein content than regular all-purpose flour, which is the secret that prevents gluten from overdeveloping and guarantees a wonderfully soft and tender, “shortbread-like” crust.²
3. The CHILL is CRUCIAL for Clean Cuts!: This is the single most important, professional secret to a perfect, beautiful bar that doesn’t crumble and fall apart. You must let the bars cool completely in the pan before you even think about slicing them. This crucial, patient step is the key that allows the hot, molten date filling to set up, which is the magic that will allow you to get beautiful, clean, and professional-looking squares. Do not skip this step!

Step-by-Step to the Best “Gramma’s” Date Squares

This elegant, festive dessert is a joy to prepare.

Part 1: The Art of the “Two-in-One” Oatmeal Crumb

Step 1: First, preheat your oven to 350°F ($175^{\circ}C$).

Step 2: In a large bowl, combine your 1 1/2 cups of rolled oats, 1 1/2 cups of sifted pastry flour, 1 cup of the packed brown sugar, 3/4 teaspoon of baking soda, and 1/4 teaspoon of salt.

Step 3: Add your 3/4 cup of softened butter to the bowl. Use a pastry blender or your fingers to mix the butter into the dry ingredients until the mixture is crumbly.

Step 4: Press half of this crumb mixture evenly into the bottom of a 9-inch square baking pan to create your base.

Part 2: The Rich and Jammy Date Filling

Step 1: In a small saucepan, combine your 3/4 pound of diced dates, the 1 cup of water, and the remaining 1/3 cup of brown sugar.

Step 2: Bring the mixture to a boil over a medium heat, and then cook, stirring, until the mixture has thickened into a jammy paste.

Step 3: Remove the pan from the heat and stir in your 1 teaspoon of lemon juice.

Part 3: The Festive Assembly and Final Bake

Step 1 (The Fun Part!): Spread your hot date filling evenly over the top of the unbaked crust.

Step 2: Sprinkle the remaining half of your crumb mixture evenly over the top of the date filling.

Step 3: Bake for 20 to 25 minutes. You will know the bars are perfectly done when the top is a beautiful, light golden brown and lightly toasted.

Step 4 (The Most Important Step!): You must let the bars cool completely in the pan before you cut them into 12 squares.

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What to Serve With Your Date Squares

These beautiful and nostalgic bars are a fantastic, all-in-one treat that are perfect on their own!

• The Perfect Pairing: They are absolutely perfect served on a holiday cookie platter alongside other classics like shortbread, gingerbread, and “Grandma’s Snowball Cookies.”
• A Cozy Treat: They are the perfect, chewy, and satisfying bite to enjoy with a cup of hot coffee, a cup of tea, or a tall, cold glass of milk.

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Storage and Make-Ahead Tips

These are the ultimate make-ahead holiday treat!

• Make-Ahead: This is a perfect make-ahead recipe! You can bake the entire, uncut slab up to 2 days in advance.
• Storage: Store the finished, cut squares in an airtight container at room temperature, with sheets of wax paper between the layers, for up to 1 week.
• Freezing: These bars freeze beautifully! You can freeze the entire, uncut slab or the individual, cut squares for up to 3 months.

Frequently Asked questions (FAQs)