Measure 2 cups of vanilla ice cream. Spoon it into the blender.
Measure 2 oz of peanut butter whiskey with the jigger. Toss that into the blender.
Measure .5 oz of milk. Toss that into the blender.
Turn the blender on - smoothie setting works well. But you may need to vary depending on your blender.It just needs to run long enough to thoroughly mix everything together.
Take the hurricane glass and drizzle chocolate syrup all around the inside of the glass.
Pour the milkshake from the blender into the glass.