Blend on high until very creamy and without any chunks, streaming in water as needed.
Taste. If the pudding is not chocolatey enough, mix in additional cacao powder about 1 tablespoon at a time. If not sweet enough, add more dates, blending in 1 or 2 at a time. If needing to blend more, use water only as needed.
Taste again to make sure the flavor is perfect. Scoop into serving bowls and chill if desired, or top with your toppings and enjoy as is.