Place the cookies in a ziplock bag and crush them up into small chunks. Place the crushed cookies on a plate. Spread frosting around the rim of your glasses and roll them in the cookies.
Blend the ice cream and milk in a blender until smooth. If desired, mix in the remaining cookies and/or sauces and blend (for a smoother milkshake) or stir (to keep some larger cookie chunks).
Pour into glasses and top with whipped cream and a cookie!