Preheat the oven. Preheat your oven to 250°F. Line a baking sheet with parchment paper.
Make the shortbread dough. In a medium bowl, mix almond flour and maple syrup until a smooth dough forms. Place the dough between two sheets of parchment paper and roll out to 1/4 inch thickness.
Cut out the cookies. Use a round cookie cutter or wide jar lid to cut circles. Use a metal straw or small cutter to press a hole in the center of each circle. Re-roll scraps and repeat.
Bake. Transfer cookies to the prepared baking sheet. Bake for 25–30 minutes, until set and lightly golden. Let cool completely on a wire rack before assembling.
Make the date caramel. Remove pits from dates and place in a bowl. Cover with nearly boiling water and soak for 10 minutes. Drain and transfer to a food processor. Process on high for 3–5 minutes until completely smooth and creamy, adding water 1 tablespoon at a time if needed. Set aside.
Toast the coconut. Heat a dry skillet over medium heat. Add shredded coconut and stir constantly for 3–5 minutes until golden and fragrant. Watch closely - it burns quickly. Transfer to a plate to cool. (Oven method: bake at 350°F for 3–5 minutes, checking frequently.)
Assemble the cookies. Spread a generous layer of date caramel on top of each cooled cookie. Press the caramel side into the toasted coconut, or sprinkle coconut on top and press gently to adhere. Alternatively, mix the caramel and coconut together first and spread as one layer.
Add the chocolate. Melt chocolate chips and coconut oil together in the microwave in 30-second intervals, stirring between each, until smooth. Dip the bottom of each cookie into the melted chocolate. Place back on parchment and drizzle remaining chocolate over the tops.
Set and serve. Place cookies in the freezer for 20–30 minutes to set. Enjoy chilled from the fridge or freezer.
