1. In a mixing bowl, beat softened cream cheese with an electric mixer until smooth.
2. Slowly begin beating the milk into the cream cheese. Mix in a little milk at a time until the mixture is smooth and creamy. As you add more milk, switch to a whisk to mix in the rest to minimize splatter.
3. Sprinkle pudding mix over the milk mixture and whisk for several minutes until the mixture thickens.
4. Fold in 1 cup of whipped cream.
5. Slice 2 bananas and fold the pieces into the pudding mixture.
6. Build the trifle by layering 1⁄3 of the pudding mixture, 1⁄3 of the remaining whipped cream, and 1 1⁄2 cups of crushed Nilla wafers per layer. Make three layers each of pudding and whipped cream and two layers of Nilla wafers.
7. After the first layer of pudding and whipped cream, place whole Nilla wafers around the perimeter of the trifle bowl if you’d like a decorative look to the trifle. After the second layer of pudding, whipped cream, and cookies, place a circle of banana slices (use the remaining banana) for another decorative touch.
8. Layer the third and final portions of pudding and whipped cream.
9. Place a couple of whole Nilla wafers and some crumbles on top for decoration.

**Expert Tips & FAQs:**

– For the whipped cream, you can either whip heavy whipping cream with sugar until stiff peaks form or use Cool Whip as a quicker option.
– Use instant vanilla pudding for this recipe for proper setting.
– Soften cream cheese by leaving it at room temperature for 20-30 minutes.
– To prevent browning of banana slices used for decoration, toss them with a teaspoon of lemon juice.
– If making in advance, use whole Nilla wafers for decorative rings and keep banana slices protected in the pudding layers.
– To make in advance, store the trifle covered in the refrigerator until ready to serve.
– Store covered in the refrigerator for up to 3 days.
– Freezing is possible but not recommended due to bananas and whipped cream.