Preheat the oven to 350°F. Line a cookie sheet with parchment paper or a silicone baking mat. Set aside.
In a food processor, pulse the dates and the almonds until they are finely chopped. Add the oat flour, eggs, chia seeds, flax meal, rolled oats, honey, salt, vanilla, cinnamon and cocoa powder and process until the mixture is well combined and comes together into a dough. Add the mini chocolate chips and pulse a few times to mix them in evenly.
Scoop the dough by the tablespoonful (a one tablespoon cookie scoop works well for these) onto the prepared baking sheet, spacing them one to two inches apart.
Lightly grease the end of a wooden spoon and use it to make a small indentation in the top of each cookie (or just make a hole with your thumb).
Place 1/2 teaspoon of the cherry jam or jelly into the hole in each cookie.
Bake for 10 minutes, then allow to cool on the cookie sheet for 5 minutes before removing the cookies to a wire rack to cool completely.
Once the cookies are completely cool, whisk together the powdered sugar, milk and vanilla in a small bowl, adding a little more milk if it’s too thick. Drizzle the glaze across the cooled cookies, you might not need it all.
Allow the cookies to sit out for several hours and then store them in a container that is NOT airtight at room temperature. If you keep them in an airtight container they will get sticky to the touch, they keep the cookie like texture if they are stored in a non-airtight container. They keep well for up to one week.
You can use any kind of jam/jelly for these cookies, I used a homemade cherry jelly that was quite low sugar to keep them as healthy as possible. You could also omit the glaze if you’d like to eliminate the processed sugar, but you might want to increase the honey by a tablespoon or two if you do that as they might not be sweet enough without it. Again, they would be a bit sweeter if you use regular jam/jelly instead of low sugar.
To make sure these cookies are gluten-free, please use certified gluten free oats and oat flour.