Preheat the oven to 350 degrees, if toasting the coconut. Soak the dates in a hot water. Spread the coconut out evenly on a baking sheet and bake for 5 minutes, or until the coconut is a light golden. Be careful not to let it burn.
In a food processor, process together the dates, toasted coconut, cashew butter, & vanilla on high until smooth, stopping occasionally to scrape down the sides.
Use a tablespoon cookie scoop to form balls and flatten them on a cookie sheet lined with parchment paper. If desired, use a smoothie straw to create a hole in the middle, reshaping if necessary. Place in the freezer.
Microwave the chocolate, stopping every 30 seconds to stir, until melted. Dip the bottom of the cookies in the chocolate, lightly scraping off the excess. Spoon the remaining chocolate into a plastic bag, snip off a small corner, and drizzle the chocolate over the cookies.