In a bowl, add the instant vanilla pudding mix and the cold milk. Whisk together and let it sit for 10 minutes to thicken up.
After 10 minutes, add the sweetened condensed milk and softened cream cheese to the pudding. Whisk vigorously or use an electric hand mixer to combine. Set aside once smooth.
To a different bowl, add the heavy cream and vanilla extract. Using an electric hand mixer, beat until stiff peaks form to make whipped cream. Make sure not to over-beat it.
Combine the whipped cream with the pudding mixture and gently fold in with a rubber spatula. Set aside in the fridge.
Add Nilla wafers to a food processor and blend until fine like sand. Combine with the melted butter to form a "crust-like" mixture.
Now assemble. You can assemble in individual cups or in a large casserole dish or trifle bowl.
Add the crust at the bottom. Then add a layer of sliced bananas. On top, goes Nilla wafers, then a thick layer of the vanilla pudding. Repeat with a layer of bananas, Nilla wafers, and another thick layer of vanilla pudding. Usually, two layers fills up my cups or dishes.
Allow it to sit on the fridge for at least 6 hours to soften up.
Right before serving, garnish on top with one Nilla wafer, a banana slice, and crushed Nilla wafers and enjoy!