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 peanut butter to a zip-top bag or pastry bag. Slightly warm the peanut butter by gently working it in your hands to make it easier to pipe into the dates. Cut a small corner off of the bag and pipe about a ½ teaspoon into each date. Sprinkle each date with chopped peanuts.

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.

Refrigerate for 10 to 15 minutes to allow the chocolate to set. Store in an airtight container in the fridge for up to 1 week or in the freezer for up to 1 month.