Start by pitting and chopping about 8 Medjool dates into small pieces. In a saucepan, combine the chopped dates with 1 cup of water and bring to a gentle simmer over medium heat. Allow the mixture to simmer for about 5 minutes until the dates soften and absorb the water. Once softened, mash the dates with a fork until you achieve a smooth paste.

While the dates cool, preheat your oven to 350°F (175°C). Next, take a greased 8x8-inch baking dish and lightly coat it with butter or cooking spray, ensuring the entire base and sides are covered.

In a large mixing bowl, cream together ½ cup of unsalted butter and 1 cup of dark brown sugar until the mixture is light and fluffy, about 3-4 minutes with an electric mixer. Then, add in 2 large eggs one at a time, mixing thoroughly after each addition. Gently fold in 1 cup of all-purpose flour and 2 teaspoons of baking powder, ensuring no lumps remain, and finally, mix in the mashed date mixture until fully incorporated.

Pour the batter into the prepared baking dish, smoothing it out evenly. Bake in the preheated oven for about 35 minutes, or until the top is golden brown and a toothpick inserted into the center comes out clean.

While the pudding is baking, prepare the toffee sauce. In a saucepan over low heat, combine 1 cup of heavy cream, ½ cup of dark brown sugar, and ¼ cup of unsalted butter. Stir continuously until the mixture is bubbling and the sugar has dissolved. Once ready, remove from heat and stir in 1 teaspoon of vanilla extract.

Once your sticky toffee pudding has baked, allow it to cool for about 5 minutes before cutting it into squares. Serve warm with a generous drizzle of the toffee sauce on top.