Whip the cream. In a cold bowl, beat the heavy cream with powdered sugar and vanilla until soft peaks form. Don’t overwhip.
If using whipped topping, skip this step.
Make the pudding. Prepare the vanilla pudding according to package directions with cold milk. Let it thicken in the fridge for 5–10 minutes.
Optional cream cheese layer. Beat the softened cream cheese with a pinch of salt until smooth. Fold in half of the whipped cream to create a light, tangy base.
Prep the fruit. Slice strawberries and bananas.
Toss banana slices with lemon juice to reduce browning, then pat dry with a paper towel so the layers don’t get watery.
Combine the creams. Fold the remaining whipped cream into the chilled pudding to create a light, airy texture. Taste and adjust sweetness if needed.
Start layering. In a 9x13-inch dish or a large trifle bowl, add a single layer of vanilla wafers. Top with the cream cheese mixture (if using) or a thin layer of the pudding-cream blend.
Add fruit. Arrange a layer of bananas and strawberries over the cream.
If you like, warm the strawberry jam slightly and drizzle a thin ribbon for extra berry flavor.
Repeat. Add another layer of wafers, then more pudding-cream, then more fruit. Aim for 2–3 complete layers, finishing with the pudding-cream on top.
Top and chill. Garnish with crushed wafers and a few strawberry slices. Cover and chill for at least 3 hours (overnight is best) to let the wafers soften and flavors meld.
Serve. Spoon into bowls or slice like a soft cake.
Add extra fresh berries on top right before serving for a pop of color.