Preheat the oven to 170°C and line a 12-hole cupcake tray with cupcake liners. In a small pan, combine the chopped dates with hot water and bring to a simmer. Stir for about 5 minutes, then remove from the heat and allow the mixture to cool.
In the bowl of an electric mixer, beat the unsalted butter and soft dark brown sugar on medium speed for around 5 minutes until light and creamy. Meanwhile, sift together the self-raising flour and baking powder and set aside. With the mixer on low speed, add the eggs one at a time, mixing until fully incorporated after each addition. Add the black treacle and half of the flour mixture, and mix to combine. Pour in the cooled date mixture from Step 1 and the vanilla extract, then add the remaining flour mixture and mix until just combined. I like to stop mixing once everything looks just blended to keep the cupcakes tender.
Using an ice cream scoop or two spoons, fill the lined cupcake cases two-thirds full with the batter. Bake in the preheated oven for about 20 minutes, or until the cupcakes are golden brown and springy to the touch. Allow the cupcakes to cool in the tin for 5 minutes before transferring them to a wire rack to cool completely.
In the bowl of an electric mixer, beat the unsalted butter until pale and soft. Add the sifted powdered sugar, soft dark brown sugar, vanilla extract, and 2 tablespoons of milk. Begin mixing on low speed and gradually increase the speed, whipping for about 5 minutes. If the frosting is too stiff, add additional milk a little at a time until you reach a smooth, pipeable consistency. For an extra luxurious touch, I always use whole milk in the frosting for better richness.
Once the cupcakes have completely cooled, fill a piping bag fitted with an open star nozzle with the vanilla frosting from Step 4. Pipe a swirl of frosting onto each cupcake. Finish by drizzling each one with warm caramel sauce and sprinkling with fudge pieces. I like to be generous with the caramel for a true sticky toffee experience.