Preheat the oven to 250°F and line a baking sheet with parchment paper.
In a medium bowl, mix almond flour, maple syrup, and vanilla extract to make the shortbread dough.
Scoop the dough using a double cookie scoop, roll it into balls, flatten them, and place them on the baking sheet. Make an indent in the center of each cookie using the back of the cookie scoop.
Bake for 25-27 minutes, then let cool completely.
While the cookies cool, soak the pitted dates in hot water for 10-15 minutes. Drain and blend them in a food processor until smooth to make the date caramel.
Spread the date caramel onto the cookies and freeze for 10-15 minutes.
Melt the dark chocolate with coconut oil, coat the cookies, and return them to the freezer for another 10-15 minutes until fully hardened.
Once hardened, remove from the freezer and enjoy your delicious Twix Cookies!