In a medium bowl, combine 1 cup of chopped Medjool dates with 1 teaspoon of baking soda. Pour 1 cup of boiling water over the mixture and let it sit for 10 minutes. Mash the dates slightly with a fork.

In a large mixing bowl, cream together ½ cup of softened unsalted butter and 1 cup of brown sugar for about 2-3 minutes. Add 2 large eggs, one at a time, then stir in 1 teaspoon of vanilla extract until pale and airy.

Sift together 1½ cups of all-purpose flour, 1 teaspoon of baking powder, and a pinch of salt into the butter mixture. Fold in the flour until just combined. Add the date mixture, folding until evenly incorporated.

Preheat your oven to 350°F (175°C). Grease an 8-inch square baking dish or individual ramekins. Pour the batter in and smooth the top. Bake for 30-35 minutes until springy and a toothpick comes out clean.

In a saucepan over medium heat, combine 1 cup of brown sugar, 1 cup of heavy cream, and ¼ cup of unsalted butter. Stir until it comes to a gentle boil, then simmer for 3-5 minutes until slightly thickened. Stir in 1 teaspoon of vanilla extract and a pinch of salt.

After cooling the pudding for 10 minutes, poke holes in the top and pour warm caramel sauce over it. Serve warm with extra caramel sauce and consider adding vanilla ice cream.