Whip the cream. In a cold bowl, whip heavy cream with 2–3 tablespoons sugar and 1 teaspoon vanilla until medium-soft peaks form.
Chill. If using whipped topping, skip this step.
Mix the pudding. Whisk instant vanilla pudding with cold milk until thick, about 2 minutes. Let it sit for 5 minutes to fully set.
Make the cream layer. Beat softened cream cheese with the sweetened condensed milk and a pinch of salt until smooth.
Stir in the set pudding, then gently fold in the whipped cream or whipped topping until no streaks remain.
Prep the fruit. Slice strawberries. Slice bananas and toss lightly with lemon juice to slow browning. Pat fruit dry with paper towels so the pudding doesn’t get watery.
Layer the base. In a 9x13-inch pan or trifle dish, add a layer of vanilla wafers.
Fit them snugly but don’t stress over perfect coverage.
Add fruit and cream. Spread a thick layer of the pudding-cream mixture over the wafers. Top with an even layer of sliced bananas and strawberries.
Repeat. Add another layer of wafers, more cream, and more fruit. Finish with a final swoosh of cream on top and a few pretty strawberry slices for garnish.
Chill to set. Cover and refrigerate at least 4 hours, ideally overnight.
The wafers soften and the flavors meld, giving you that classic pudding texture.
Serve. Spoon into bowls or cut into squares if your layers are firm. Add extra fresh berries right before serving if you like.