To make the ice cream, blend all the ingredients together until creamy and smooth.
To make the caramel, place the dates, nut butter, and vanilla in a food processor and process until smooth. If necessary, add a little water, one teaspoon at a time, to help blend until smooth and spreadable.
Use a small spoon to spread the caramel in each of the ice cream molds. Pour the ice cream mixture over the caramel and fill to the top. Depending on your ice cream molds, insert a popsicle stick into the slot. Carefully place molds on a small tray and freeze for about an hour or more.
Before removing the molds from the freezer, melt the chocolate together with the coconut oil in the microwave or in a small pot over low heat, being careful not to overheat the chocolate. Stop the melting before all the chips are melted and let the heat of the melted chips do the rest of the work.
