In a small saucepan, melt 2 Tbsp butter and 1 apples worth of diced apple, and maple syrup. Saute until apple is tender, set aside.
In a food processor, add oatmeal and dates. Pulse a few times until there are no large chunks. Add to the bowl of the stand mixer.
In a food processor add remaining butter (softened), sugars, egg, vanilla, and remaining apple. Pulse until fully combined.
Add flour, salt, baking soda, and cinnamon to the bowl of the stand mixer and mix to combine.
Add sugar mixture from food processor to bowl of stand mixer and mix to combine thoroughly. Stir in sauteed apple mixture.
Place dough in the freezer for 15-20 minutes.
While the dough is in the freezer, preheat oven to 350°.
Place dough by spoonfuls onto prepared cookie sheet, be sure to leave at least 2 inches between each cookie.
Bake 15-18 minutes, or until golden brown.
Allow to cool on the cookie sheet for 5-10 minutes before transferring to a wire rack and allowing to cool completely.