Mix together date sugar and almond flour in a medium-sized bowl.
Add date syrup, aquafaba, and cherry vinegar and mix until a dough begins to form. Let rest for 5 minutes. If the dough feels too sticky, gradually add more date sugar, 1 tablespoon at a time, until it becomes smooth and pliable.
Lightly dust a clean work surface with more date sugar. Roll out the dough to a thickness of ¼” to ½”. Use a 1 ½” round or heart-shaped (or other shapes) cookie cutters to cut out shapes. Place the shapes on a parchment-lined baking sheet. Freeze for 20-30 minutes until firm.
Melt chocolate in the microwave at 50% power in 30-second increments, stirring in between.
Coat each piece in the melted chocolate. Place in the refrigerator for at least 30 minutes to let the chocolate harden.
Store airtight in the refrigerator with parchment paper between layers.