Place the chopped chocolate in a small bowl, then set aside.
In a saucepan, heat the almond milk over medium heat. Just before it starts boiling, remove it from the heat and pour it into the dark chocolate bowl. Let sit for about 3 minutes to let the chocolate melt. Whisk well to combine the melted chocolate with the milk.
Let it cool at room temperature while you prepare the cookies and the date caramel. After about 30-40 minutes it will have thicken and have the consistency of a paste. If it's still too soft, place the bowl in the refrigerator for 30 minutes.
Caramel
Place the pitted medjool dates in the bowl of a food processor and process until you get a smooth paste. Add the water only if needed, if your medjool dates are very moist you won't need it. You want a thick and smooth consistency. Set aside.
Cookies
Preheat oven to 350°F.
In a large bowl, whisk together the rice flour, arrowroot, almond flour, baking soda, baking powder, and coconut sugar.
Melt the coconut oil over low heat until just melted. Combine the coconut oil with the almond milk, applesauce and vanilla extract.
Slowly pour in the wet ingredients into the dry ingredients and mix until well combined using a wooden spoon. The dough will be soft but you don't need to chill it.
Line a baking sheet with parchment paper and set aside.
Transfer the dough to a piping bag and pipe 1.5-2-inch rounds of batter onto the prepared baking sheet, 3-4 inches apart, since the cookies will spread. You will probably need to cook them in 2-3 batches.
Bake 9 minutes, or until the edges are golden brown. Let cool completely before removing them from the baking sheet.
Spread about 1 tablespoon of the chocolate ganache onto the flat side of a cookie. Spread a tablespoon of date caramel on top of the chocolate ganache and sandwich with another cookie. Repeat with the remaining cookies.
Chocolate shell (optional)
Melt the dark chocolate with the coconut oil in a double boiler over medium heat.
Gently dip each cookie sandwich in the melted chocolate. You can use a fork or a dipping tool to make things easier. Make sure to tap your fork on the side of the bowl to let excess chocolate drip back into the bowl. Transfer the cookies to a baking sheet lined with parchment paper and let cool for at least 1 hour.
Store the cookies at room temperature in an airtight container for up to 3 days or 5 days in the refrigerator.
Notes
If dipping the cookies, make sure to use a chocolate with a high percentage of cocoa butter (70% dark chocolate for example); it will result in a thinner coating.