In a medium size mixing bowl, mix together the cream cheese, peanut butter, and sweetened condensed milk until smooth.
Stir in the milk and the pudding mix. Refrigerate for 30 minutes.
In a chilled stainless steel bowl, beat the heavy whipping cream until stiff peaks form.
Fold the whipped cream into the pudding mixture.
Cover and refrigerate until ready to assemble the trifle.
FOR THE WHIPPED CREAM
In a chilled stainless steel bowl, beat the heavy whipping cream and powdered sugar until stiff peaks form.
ASSEMBLY
I recommend doing the assembly just a few hours before you want to serve the trifle. If you make the trifle too far in advance, the cookies will get soggy. Soft is ok, but we don’t want them soggy.
Cover the bottom of your trifle bowl (or mason jars, paper cups, etc.) with a layer of Nilla wafer cookies.
If doing a trifle, cover with ⅓ of the peanut butter banana filling, sliced bananas, then ⅓ of the whipped cream. If you're using mason jars or another container for individual servings, you'll want to break up a couple cookies, add a scoop of the peanut butter banana pudding, some sliced bananas, and a scoop of whipped cream.
Repeat these steps two more times.
Refrigerate until you're ready to serve.
Notes
Feel free to swap out Nilla wafers for shortbread cookies, Nutter Butters, Oreos or even graham crackers.
If you're not doing a trifle, you could also split this recipe in half for smaller individual servings.