Do ahead: Pour 1¾ cups of the coconut milk (about 1 can) into an ice cube tray and let chill at least 4 hours or overnight, until solid.
Pour boiling water over the dates and let sit for 5 minutes to loosen them up. Rinse with cool water and drain well.
In a blender, combine the coconut milk cubes with the remaining ½ cup coconut milk, drained dates, and the rest of the ingredients. Blend until completely smooth. Divide between two cups (or store half in a sealed jar in the fridge for up to 48 hours).
If making whipped coconut, transfer only the solidified cream off the top of the chilled coconut cream can into the bowl of a stand mixer fitted with the whisk attachment. Whisk on medium-high speed until it begins to thicken. Add the vanilla extract, and continue whipping until stiff peaks form. Spoon this over the top of the milkshake just before serving.
Sprinkle with cacao nibs and serve with a thick straw.
This nutritional information has been automatically calculated, and as such, may be incomplete or inaccurate. Please reference the specific ingredients you use for the most accurate nutritional information.