Think the warm, caramelized flavors of sticky toffee pudding — dates, brown sugar, cinnamon — baked into a buttery thumbprint cookie and filled with silky toffee sauce. Those decadent cookies happen to be the ideal holiday cookie swap showstopper, afternoon tea accompaniment and Sunday-night-in dessert for date night. Crispy edges and chewy centers with pools of molten toffee make these impossible to resist!

Ingredients
(Makes 24 cookies)
Cookie Base:
- 1 cup (2 sticks) unsalted butter, softened
- ¾ cup packed dark brown sugar
- 1 large egg, room temperature
- 1 tsp vanilla extract
- 2 cups of all-purpose flour (or gluten-free 1:1 baking mix)
- 1 tsp ground cinnamon
- ½ tsp baking powder
- ¼ tsp salt
- ⅔ cup Medjool dates, pitted & finely chopped (soak in hot water 10 mins if hard)
Toffee Filling:
- ½ cup heavy cream
- ½ cup dark brown sugar
- ¼ cup unsalted butter
- 1 tbsp molasses (or golden syrup)
- Pinch of flaky sea salt
Optional Garnish:
- Powdered sugar
- Chopped pecans or walnuts
- Vanilla ice cream (for serving)
Instructions
Make the Toffee Sauce
- Combine cream, brown sugar, butter, molasses and salt in a saucepan. Simmer on medium while stirring 5–7 minutes until thickened. Let cool slightly.
Prep the Cookie Dough
- Cream butter and sugar until light and fluffy (2–3 minutes). Stir in egg and vanilla until smooth.
- Whisk flour, cinnamon, baking powder and salt in a separate bowl. Fueling up the wet ingredients little by little Fold in chopped dates.
- Chill dough 30 minutes (to prevent spreading).
Shape & Bake
- Make the cake: Preheat oven to 350°F (175°C). Prepare baking sheets with parchment.
- Roll dough into 1-inch balls. Place 2 inches apart. Using your thumb (or the handle of a teaspoon), press in the center of each to form a well.
- Bake 10–12 minutes until the edges are golden. Press the wells again immediately (they puff while baking).
Fill & Finish
- Spoon ½ tsp toffee sauce into each warm cookie’s well. Let cool completely. Sift with powdered sugar and nuts (if using).
Tips & Variations
Dietary Tweaks:
- Vegan: Substitute the butter with vegan butter, the egg with a flax egg and the cream with coconut cream. Use maple syrup instead of molasses.
- Gluten-Free: Replace with GF flour blend (plus ½ tsp xanthum gum).
- Nut-Free: Omit the garnish or use seeds.
Flavor Twists:
- Boozy Kick: Stir 1 tbsp rum or bourbon into the toffee sauce.
- Spiced Up: Work in ¼ tsp nutmeg or cardamom to the dough.
- Chocolate Drizzle: Drizzle melted dark chocolate over cookies that are filled.
Time-Savers:
- Store-Bought SauceUse ½ cup prepared toffee or caramel sauce.
- Date hack: Purchase pitted, chopped dates or substitute raisins (soak them in hot water first).
Serving & Storage
Serving Ideas:
- À la Mode: Serve warm with vanilla ice cream and additional toffee drizzle.
- Giftable: Arrange in festive tins, with parchment between layers.
- Tea Time: Enjoy with chai or espresso for a cozy indulgence.
Storage Tips:
- Room Temp: Store in an airtight container for 3 days (sauce may soak in).
- Freeze: Freeze unfilled cookies 2 months. Thaw, crisp at 300°F for 5 mins. Fill.
- Sauté Separately: Chill extra sauce for up to 2 weeks; heat before using.
FAQ
Q: My cookie wells closed up while baking!
A: Immediately re-press them right out of the oven — they’re still soft.
Q: Can I use dried dates?
A: Yes! Soak in hot water (or tea!) for 15 minutes to soften it first.
Q: Sauce too thick/thin?
A: Thin with cream or thicken with 1 tsp cornstarch slurry (simmer 2 mins).
Q: Can I make these ahead?
A: Yes! Cook the cookies and keep without filling; fill with sauce before serving.
Final Thoughts
These, Sticky Toffee Pudding Thumbprints, are a love letter to sweet induces of a cozy Brit, spiced, buttery, converging, luxuriously gooey. They’re surprisingly easy to prepare but taste like you slaved away in the kitchen for hours. Pro tip: Double the toffee sauce for drizzling on ice cream (or stealing spoonfuls).
Tried them? Show us your #StickyThumbprintMagic!