Inflate the balloons so that the bottom of it is just large enough to form a small bowl when dipped into the candy. Tie the balloon off and spray with cooking spray.
Place the white candy melts into a microwave safe bowl and heat for one minute at a time on the defrost setting until completely melted.
Dip the balloons into the candy melts so the bottom ⅓-1/2 of the balloon is coated in the melted candy.
Place the coated balloons onto the parchment-lined tray and let them set for a minute or two.
Continue to dip the balloons back into the candy a total of 4-5 times to form a thicker coating. You may need to put the candy melts back into the microwave to remelt during this.
Place the coated balloons into the fridge to set for a minimum of 30 minutes.
Use a pin to deflate the balloons and remove the candy bowls that are left behind.
Place the instant pudding mix into a bowl and whisk in the milk until thoroughly combined. Let the pudding mixture set until it has thickened.
Fill the candy bowls with the pudding. Make sure there is a little empty space at the top of the bowls.
Grind the Oreo cookies into crumbs with a food processor. If you don't have a food processor, you can stick the Oreos into a ziplock baggie and use a rolling pin to smash the cookies.
Sprinkle the crushed Oreo cookies onto the top of the filled pudding bowl.
Using an edible food marker, write "RIP" on the front of each Milano cookie.
Place each cookie into the center of each dirt pudding bowl.