Make the Cookie Dough:

1. Process Sugar & Butter: In a food processor, process sugar for 30-45 seconds to make superfine sugar. Add cold butter pieces and process another 30-45 seconds until just combined.
2. Combine Wet Ingredients: Add egg, vanilla extract, and ⅛ tsp cherry flavoring. Process until just mixed, scraping down sides as needed.
3. Add Dry Ingredients: Add flour, cocoa powder, baking soda, and baking powder. Process until combined.
4. Roll & Chill Dough: Divide dough in half. Place each half between two large sheets of parchment paper and roll to about ⅛ inch thick. Refrigerate for at least 1.5 hours.

Bake the Cookies:
5. Preheat Oven: Preheat oven to 300°F (150°C) and line baking sheets with parchment paper.
6. Cut & Bake: Cut out heart shapes using a cookie cutter. Place cookies on a prepared baking sheet, ensuring it’s cold. Bake on the second-lowest rack for 20 minutes. Reroll scraps, refrigerate, and repeat.

Chocolate Coating:
7. Melt Chocolate: In a microwave-safe bowl, combine chocolate, oil, and 1-2 drops cherry flavoring. Microwave at 50% power in 30-second increments, stirring in between, until melted. Adjust cherry flavoring as needed.
8. Dip Cookies: Dip each cooled cookie into the chocolate, coating evenly and tapping off excess. Place on parchment-lined baking sheets and decorate with sprinkles if desired. Refrigerate for 10 minutes until set.

Candy Melts Decoration (Optional):
9. Drizzle: Melt candy melts in the same way as chocolate, adding a little oil if needed. Drizzle stripes over cookies and let harden for about 3 minutes.

Serve & Enjoy!