Preheat the oven to 350˚F. Spray the cookie shot mold and inserts with cooking spray.
Place about 2 tbsp of cookie dough into each mold then press the insert down so that the cookie dough comes about halfway up the sides.
Bake the cookies for about 20-25 minutes or until the cookies are set.
Remove them from the oven and place them into the fridge to cool for about 15 minutes.
While the cookies cool, place the semi-sweet chocolate chips and white chocolate chips into two separate bowls. Microwave each of them in 30 second intervals, mixing after each session, until the chocolate chips are completely melted. Transfer the white chocolate to a piping bag.
Take the pan out of the fridge and remove the cookies from the mold. Use a pastry brush to coat the inside of each cup with the melted semi-sweet chocolate. Transfer the remaining semi-sweet chocolate into a piping bag.
Cut off a small section of the tip from the piping bags. Use the semi-sweet chocolate to pipe two dots for the eyes, an inverted triangle for the nose, a semi-circle for the mouth, and a strip for the sash. Then use the white chocolate to pipe the teeth inside the mouth and the design for the sash.
Place the cookies in the fridge for about 10 minutes to allow the chocolate to harden.
Pour the milk into a pitcher. Add a few drops of blue food coloring and mix. If needed, add more food coloring to get the desired color.
Remove the cookies from the fridge and pour the blue milk into each cookie shot. Enjoy!