Please note that ingredients are per serving. Ice cream and milk are approximate - just how big do you want the shakes to be?
Freeze serving glasses.
Melt chocolate in a bowl big enough to dip the tops of the glasses in. Use 30 second increments in the microwave, stirring between rounds until smooth. Allow to cool but not solidify. You do not want to shock the frozen glasses, as they could crack if the temperature difference is too great.
Dip tops of cups in melted chocolate.
Dip tops of cups in sprinkles or add small candies by hand. Return glasses to freezer.
Place a dollop of chocolate on the cookie. Put gummy eye on top of the chocolate. Refrigerate to solidify the chocolate.
Defrost ice cream for about 10 minutes to soften.
Scoop ice cream into blender. Add milk and any other desired flavors. Blend until smooth.
Remove glasses from freezer and drizzle chocolate sauce along the insides.
Pour milkshake into glass. Stand cookie at the top of the glass. Serve.