Simmer the chocolate milk over low heat in a small pot. Remove from heat and set aside.
Bring a very small pot filled with 1-2 inches of water to a gentle simmer over low heat. Place the chocolate chips in a metal or other heat-safe mixing bowl, and rest on top of the pot of simmering water. Stir the chocolate chips until completely melted. Remove from heat. Add the chocolate soy milk and silken tofu to the melted chocolate chips . Use a hand blender or a regular blender to blend until completely smooth. Stir in the Amaretto and almond extract.
Transfer to individual bowls or one big bowl, and refrigerate for at least 1 1/2 hours, the longer the better.