Start by soaking the dates in boiling water for about 10 minutes until very tender, then blend until smooth or chop finely for a chunkier texture.
In a large bowl, cream the softened butter and dark brown sugar together using an electric mixer or whisk until the mixture is light, fluffy, and fragrant, about 3 minutes.
Add the eggs one at a time to the creamed mixture, beating well after each addition to ensure a smooth, glossy batter. Stir in vanilla extract for extra flavor.
Gently fold in the blended or chopped dates, mixing until evenly incorporated into the batter.
Sift the self-raising flour into the mixture and fold gently until just combined. Do not overmix to keep the batter airy and moist.
Pour the batter into a greased 20cm (8-inch) baking dish, spreading it evenly with a spatula. Bake in a preheated oven at 180°C (350°F) for 30–35 minutes, until the top is golden and a skewer inserted in the center comes out moist but clean.
While the pudding bakes, warm the caramel sauce gently in the microwave or on the stovetop until just pourable, about 1-2 minutes.
Remove the pudding from the oven and let it rest for about 10 minutes; it will set slightly but remain moist and sticky on top.
Drizzle the warm caramel sauce generously over the warm pudding, allowing it to soak into the sponge and create a glossy, sticky finish.
If desired, serve slices of pudding with a drizzle of heavy cream or a dollop of whipped cream for extra indulgence.