Line an 8x8 inch square baking dish with parchment paper.
In a large bowl, add in almond flour, peanut butter, syrup, vanilla, salt, milk and whisk together until combined. Fold in the chocolate chips. Transfer mixture to the baking pan and spread out evenly. Place in the freezer for 15 minutes.
Date Caramel Layer:
In a mini food processor pulse together the dates, peanut butter, vanilla and salt until smooth. Transfer mixture on top of the cookie layer evenly. Place back in the freezer for 20 minutes.
Chocolate Layer:
In a small pot melt your chocolate chips and coconut oil on low heat, stirring constantly until smooth and melted. Transfer melted chocolate on top of caramel mixture and spread out evenly. Sprinkle with flaky sea salt and freeze for 1 hour or until chocolate is hard.