Grab 6 of each type of cookie and put them in a large Ziploc bag. Crush the cookies by hand, but be careful you don't crunch them up too much. Otherwise, you'll be working with cookie dust.

After you crush them up, lay out a piece of parchment paper and pour your cookie crumbles on to it. Spread them out evenly.

Grab your milkshake glasses, your chocolate frosting, and a butter knife or rubber spatula and spread the frosting evenly around the top of the milkshake glasses. This creates the base for which your cookie crumbles will stick to. I found that by applying a thicker coat of frosting creates a better base for your cookie crumbles. If you don't have enough on there, you will have a less chance of success with this step. So load it on!

Take your freshly frosted milkshake glass and lightly roll it in the cookie crumbles. Try not to press too hard otherwise it will smear the frosting on the glass and won't stick as well. Only roll the glass in the cookies once, then you can piece in any empty spots with more cookie crumbles where you see fit. You should have leftover cookie crumbles- set those aside because you will use those for the topping on the finished milkshake later.

Go through and press in your cookie crumbles to make sure they stay in place. Take your blue sprinkles and sprinkle them over any other open-frosted spots on the glass. Piece them in and press them down slightly. Now that your cookie crumbles and sprinkles are on your milkshake glasses, pop them in the freezer for the remainder of the time it'll take you to make the shakes, allowing them to set and harden.

Add your 5 scoops of vanilla ice cream and 1/2 cup milk to a blender.

Then add your sky blue gel food coloring to the blender as well. It's best to add a small amount at first, and if you are unhappy with the color outcome, add a little more.

Pour your cookie monster freak shake mixture into your chilled glasses. Add whip cream to the top.

Top with your blue sprinkles and the leftover cookie crumbles.

Add your adorable Cookie Monster cookies to the top of your milkshake (place in the middle). Don't forget a cute striped straw!