In the meantime make the chocolate cups. Melt about 12 ounces of the chocolate in a microwave safe bowl on 30 second intervals, stirring after each, until melted and smooth. Place 12 cupcake liners in a cupcake mold. Using the back of a spoon or a pastry brush to smooth the chocolate up the sides of the liners. Place in the freezer for 10 minutes or the fridge for 20.
When the cookies are chilled and ready to go make the cookie dough. Place the butter in the bowl of a stand mixer of a large mixing bowl. To the bowl add the brown sugar, cream or coconut milk and vanilla. Beat until combined, fluffy and light in color. Beat in the flour and salt until combined. Stir in the chocolate chips. Remove the cookie dough and add to a new bowl, set aside.
In the same mixing bowl you mixed the cookie dough in add the peanut butter and vanilla. Mix until smooth and combined.
To assemble the cups, grab the cooled cookies and cut the very outside edges off and save them for eating! Then cut the cookie into 6 rows horizontally. Then cut each row into four squares. You should now have 24 cookie squares. *Note that you only need 12 of the cookie squares, so either save the rest for eating, or make 12 more cups (doubling the chocolate cups, peanut butter and cookie dough layers) or halve the cookie recipe and press it into an 8x8 baking dish.
Now grab the chocolate cups from the fridge. Working with the chocolate cups still in the cupcake molds, place a cookie in the bottom of each. Spread a layer of cookie dough over the cookie and then a layer of peanut butter.
Melt the remaining chocolate in a microwave safe bowl on 30 second intervals, stirring after each, until melted and smooth. Carefully spoon the chocolate over the peanut butter layer completely covering the peanut butter.
Place in the fridge for at least 30 minutes before serving.
These can be stored in a cool area, but are best right out of the fridge