Preheat your oven to 350F.
Spray six 4-oz ramekins with baking spray and place on a baking sheet. Set aside.
Add the dates and the water to a small saucepan, making sure the dates are covered as much as possible by the water, and set it over medium heat. Bring mixture to a boil, then reduce heat to low and let simmer until the water is almost completely absorbed and the dates have softened (about 15-20 minutes). Remove from heat and set aside.
In a small bowl, whisk together the flour, baking powder, baking soda, and pinch of salt.
In a medium bowl, use an electric handmixer to cream together the 1/4 cup softened butter and brown sugar until light and fluffy. Beat in the egg and the vanilla extract.
Now that the dates have cooled slightly, scrape the dates and any remaining liquid into a small food processor. Blend into a smooth puree.
Scrape the date puree into the butter and egg mixture and beat until comined, then beat in the flour mixture on low.
Scoop the cake batter into the greased ramekins so all cakes are about even. Smooth the tops, then place the baking sheet with the ramekins into the oven. Bake at 350F about 20 minutes, or until a toothpick inserted into the center of a cake comes out clean. Remove from oven but keep oven on!
**Note: if making Sticky Toffee Pudding in advance, see my Recipe Notes below. If making this all in one day, keep going with the recipe.**
Let cakes cool about 10 minutes in the ramekins. Slice the tops off the cakes to make them level with the rims of the ramekins. Run a knife around the cakes and turn out onto a cooking rack. Slice each cake horizontally in half.
Get your cooled-but-still-warm toffee caramel sauce and spoon 1 tbsp into the bottom of each ramekin. Place the bottom layers of the cakes in each ramekin, cut side up. Add another 1 tbsp of sauce to each ramekin, then top with the remaining cake layers. Spread a final tablespooon of sauce over each cake.
Place the ramekins back on the baking sheet and bake for another 10 minutes at 350F until the cakes are bubbling slightly.
Remove cakes from oven and turn oven off. Let cakes cool 5-10 minutes, then run a knife around the insides of the ramekins, and invert out each Sticky Toffee Pudding onto a plate. Top with additional warm caramel sauce and, if desired, whipped cream or ice cream.