Start by chopping the Medjool dates into small pieces and soaking them in boiling water for about 10 minutes until soft. Drain and set aside.
In a saucepan, melt the butter over medium heat, then add the dark brown sugar and stir until combined and bubbling, about 2 minutes, filling your kitchen with a warm caramel aroma.
Add the drained dates to the butter-sugar mixture, then stir in vanilla extract. Cook gently for about 2-3 minutes until fragrant and slightly thickened.
In a mixing bowl, whisk together the flour and baking powder. Gradually pour in the warm date mixture, folding gently until the batter is smooth and thick but still pourable.
Pour the batter into a small greased baking dish, smoothing the top with the back of a spoon. Place it in a preheated oven at 180°C (350°F) and bake for 25-30 minutes, until the top is golden and a toothpick inserted into the center comes out with moist crumbs.
While the pudding bakes, prepare the toffee sauce by melting butter in a saucepan over low heat. Add dark brown sugar and heavy cream, bringing to a gentle simmer and stirring until the sauce is glossy and slightly thickened, about 3-4 minutes.
Once baked, check that the pudding is golden and risen with a slightly cracked top. Let it cool for about 10 minutes to settle.
Pour the warm toffee sauce generously over the pudding, allowing it to soak in and coat the top beautifully.
Serve slices of the pudding warm, topped with extra sauce, and enjoy the rich, sticky, caramelized flavors with a dollop of cream or a scoop of ice cream if desired.