Drizzle chocolate inside each of the glasses and place them in the fridge (or the freezer if you have freezer-safe glasses) while doing other steps. It prevents the chocolate from simply running to the bottom of the cup and gets the cup cold.
Add ice, milk, chocolate sauce, and chocolate chips to the blender.
Secure your blender’s lid properly and blend. Using low speed, blend for about 30 seconds. Then, up it to around max speed for about 20 seconds. All blenders are different, so you’ll have to use your best judgment.
After you’ve mixed it thoroughly, taste test it for thickness and flavor. If you’d like it thicker, add more ice cubes.
If it needs more chocolate, add more chocolate sauce and chips. Blend again if you’ve added any extra ingredients.
Pour the mixture into your prepared glasses. Add whipped cream and drizzle some chocolate sauce on the top.
Serve the drink immediately, and enjoy! Add a straw to the top for maximum drinkability.