In a large mixing bowl, beat the softened cream cheese with a hand mixer on medium speed until completely smooth and fluffy, about 2 minutes. Add the sweetened condensed milk and vanilla extract and beat until fully incorporated.

In a separate bowl, whisk the instant pudding mix with the cold whole milk for 2 minutes until thickened. Fold the pudding mixture into the cream cheese mixture until smooth and well combined. Set aside.

Pour the cold heavy cream into a chilled mixing bowl. Beat with a hand mixer or stand mixer on medium-high speed until soft peaks begin to form. Add powdered sugar and vanilla extract, then continue beating to medium-stiff peaks. Do not over-whip.

Gently fold approximately two-thirds of the whipped cream into the pudding mixture using a rubber spatula. Reserve the remaining one-third for the topping.

In a large trifle bowl or 9x13-inch baking dish, spread a thin layer of the pudding mixture across the bottom. Arrange a single layer of vanilla wafers over the pudding, covering as much surface area as possible.

Add a layer of sliced bananas over the wafers, covering them in a single layer. Spoon a generous layer of the pudding mixture over the bananas and spread evenly.

Repeat the layering process — wafers, bananas, pudding — until all components are used, finishing with a final layer of pudding on top. Aim for at least 3 complete layers.

Spread the reserved whipped cream over the top in an even layer. Garnish with a few whole vanilla wafers and crushed wafer crumbs. Cover tightly with plastic wrap pressed gently against the whipped cream surface.

Refrigerate for a minimum of 4 hours, or overnight for best results. The wafers will soften dramatically as they absorb the pudding, creating that classic soft, cake-like texture throughout.

Serve cold, scooping through all the layers so each portion gets a bit of every element. Garnish individual servings with extra banana slices if desired.