First, begin by preparing the Caramel Layer. Blend the dates in a blender with some of the coconut milk until fully smooth. Add the blended dates to a small pot with the rest of the coconut milk, maple syrup, salt, and vanilla. Bring to a boil over medium heat, and then reduce heat and allow the caramel mixture to simmer, stirring occasionally. Allow the caramel mixture to reduce down to about half, this will take about 45-50 minutes of simmering over low heat.
While the Caramel Layer is simmering, prepare the Shortbread Base. Preheat oven to 350 degrees Fahrenheit. Add coconut flour, almond flour, coconut oil, maple syrup, and salt in a bowl. Stir to combine. Pat evenly and firmly into a 9x9 baking dish. Bake in preheated oven for 10 minutes. Remove from oven and let cool.
Once the caramel mixture has reduced after 45-50 minutes, whisk in 1 tablespoon of cornstarch while simmering to thicken the mixture slightly. Remove from heat. Allow the caramel to cool slightly before pouring over the shortbread base. Place the shortbread and caramel base into the freezer to firm for 20-30 minutes or longer.
Once firm, slice into 11 strips and then slice the strips in half. Place the cut strips back into the freezer to firm again while you melt the chocolate.
Either melt the 8oz of dark chocolate until smooth or prepare the Chocolate Coating.
To prepare the chocolate coating, melt coconut oil, then add cocoa powder and maple syrup. Stir to combine.
Dip the frozen shortbread caramel strips into the melted chocolate or chocolate coating. Place on a cookie sheet and place in the freezer to set again. If desired, drizzle additional chocolate or chocolate coating over the set bars and top with sea salt.
Store in the freezer for up to 2 months. Enjoy directly from the freezer or allow to thaw for a couple of minutes before enjoying.