Soak the Medjool dates in a bowl of very hot water for 10 minutes, then line a mini muffin pan with mini liners.
Melt together the chocolate chips and coconut oil in either the microwave or over a double boiler until completely melted and smooth.
Once the chocolate is melted, pour about 1 teaspoon of melted chocolate into the bottom of each mini muffin liner and use a spoon to spread the chocolate around to cover the entire bottom of the liner. Once all liners are lined with chocolate, transfer your muffin pan to the freezer to set and place the remaining melted chocolate aside for now.
Once the dates are very soft, drain them from the water and transfer the soaked dates to a food processor or high-speed blender and blend until they are mostly smooth, scraping down the sides of the food processor or blender as needed.
Spoon about 1-2 teaspoons of date caramel into each cup lined with chocolate. Repeat this process until all cups have been filled with date caramel.
Pour 1-2 teaspoons of melted chocolate over each date caramel cup, making sure you completely cover the date caramel inside. Once all cups are filled with chocolate, transfer the pan back into the freezer for 10-15 minutes or until the chocolate is completely set. Remove date caramel cups from the freezer, transfer to an airtight container and store in the fridge or enjoy right away!