In a medium bowl, combine the milk and pudding mix; beat at medium speed with an electric mixer for 2 minutes. Set aside.
In a medium bowl, combine the peanut butter and confectioners' sugar; beat at medium speed with an electric mixer until creamy. Add the cream cheese, beating until smooth. Fold in the whipped cream topping, mixing to combine.
In serving glasses, layer the pudding, bananas, peanuts, peanut butter mixture, and crumbled cookies, as desired. Garnish with cookies and chopped peanuts, if desired. Serve immediately, or store in the refrigerator until ready to serve.