In a food processor or blender, mix the dates completely smooth with some of the milk, then add the rest of the ingredients and blend until smooth.
Fill your popsicle molds with the mixture. Do not over fill them as the mixture will expand when freezing. Let freeze for a couple of hours or over night.
Once frozen, simply mix the chocolate and nut butter together and pop the ice cream out of the molds. Drizzle or dip the popsicles in the chocolate, let set and enjoy!