Place cashews in a bowl and cover with water. Soak for 1 to 3 hours. Drain.
Combine soaked cashews, banana, ice cubes, tofu, dates, cacao powder, vanilla extract, and 1 teaspoon soy milk in a blender. Process until smooth. Add an additional teaspoon of soy milk only if needed, in order to keep the mixture as thick as possible.
Stir in cherries and chocolate chips; pour into a bowl to serve.
