For the cookie:
2/3 cup butter
5 tablespoons sugar
1 1/3 cups flour
For the cake:
1 box red velvet cake mix
1 1/4 cups water
1/3 cup vegetable oil
3 large eggs
For the raspberry filling:
1 cup raspberries plus 6 more reserved for assembly
2 tablespoons sugar
2 tablespoons water
1/4 cup powdered sugar
For the "grey stuff":
1 (3.4-ounce) box instant vanilla pudding mix
1 1/2 cups milk
1 cup whipped topping
3 tablespoons instant chocolate pudding mix
Edible pearl sprinkles, for garnish
For the cookie:
Preheat oven to 350°F. Mix together the butter and sugar until creay, then mix in the flour. Roll out about a handful of the cookie dough on a floured surface to about 1/4-inch thickness. Use a mini tart pan (4 1/2") to cut out flower shapes. Place on an ungreased cookie sheet and bake for 15-20 minutes, or until light golden brown.
To make the cake: Mix your cake batter according to back of the box instructions and divide into a greased muffin tin about 2/3 full. Bake for about 16-19 minutes at 350°F, or until toothpick comes out clean. Cool cupcakes completely.
For the raspberry filling: Cook raspberries, granulated sugar, and water in a pot on medium heat for 10 minutes, stirring frequently. Pour through a fine mesh strainer to remove seeds. Mix in powdered sugar to thicken.
To make the "grey stuff": Whisk together vanilla pudding mix and milk into a large bowl. Chill in the fridge for 5-15 minutes, until thick. Pulse Oreo cookies in the food processor until they are a fine crumb. Take the pudding mixture out of the refrigerator and mix in the crushed Oreos. Carefully fold the whipped topping into the mixture. Mix in chocolate pudding powder. Chill for 1 to 1 1/2 hours.
To assemble: Slice the top off the cupcake, then flip the cupcake upside down on top of one of the cookies. Use a knife to cut a small cavity inside the center of the cupcake (or just use your finger to mash the center down). Fill the cavity with raspberry filling. Using a large star-shaped tip, pipe the "grey stuff" around the cake, covering it completely. Garnish with edible pearl sprinkles.