Line a large rimmed baking sheet with parchment paper. Remove and discard the stems from the dates. With a sharp knife, carefully slice the dates lengthwise to remove and discard the pits; do not cut the dates fully in half. Place the opened dates on the prepared baking sheet.

Add the coconut, almond flour, coconut oil and maple syrup to a food processor and manually pulse until a wet and sticky mixture forms, but there are still noticeable pieces of coconut; scrape down the sides and bottom of the food processor as needed to incorporate all of the ingredients. Add about 1 teaspoon of the coconut mixture to each date.

In a microwave-safe dish, combine the chocolate chips and olive oil and microwave for 15-second increments, stirring after each cycle, until smooth and melted.

Carefully pour the melted chocolate into a zip-top bag or pastry bag. Cut a small corner off of the bag and generously drizzle over each date. Top each date with an almond.

Place in the freezer for 10 to 15 minutes to allow the chocolate to set and the coconut mixture to firm up before serving. Store in an airtight container in the fridge for up to 1 week or in the freezer for up to 1 month.