Whisk the milk, vanilla extract, and pudding together until combined and slightly thickened or for about 2-3 minutes.
Fold in the whipped topping, then mix in the chopped bananas, cover in saran wrap, and place in the fridge to chill while you make the cookies.
Preheat the oven to 350F then line a baking sheet with parchement pape and set aside.
Cream the butter, oil, Imperial Sugar granulated sugar, and Imperial Sugar powdered sugar in a large mixing bowl or in a stand mixer.
Add the egg, and vanilla butter emulsion and mix until combined.
Add the flour, salt, and baking powder and mix until combined, using a large cookie scooper, scoop out 9 equally sized cookie balls, place them on the prepared baking sheet, gently flatten them to about 1 inch in thickness, then using a ¼ measuring cup, press down the center of the cookie to make a well for the filling.
Bake for 10 minutes then cool on the baking sheet fully.
Once the cookies are cooled, top with the banana pudding mixture, Nilla wafer crumbs, and a mini Nilla wafer in the center, and enjoy!
