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Step 2
Make the Pudding: In a medium heatproof bowl, whisk together the sugar, cornstarch and salt. Set aside.
Step 3
In a medium saucepan over medium heat, heat the milk just below a simmer. (You should see bubbles form at the edges, but no boiling.) While whisking constantly, slowly stream the hot milk into the sugar mixture to dissolve. Return the mixture to the saucepan. Continue to cook over medium heat, stirring constantly with a silicone spatula, until the pudding coats the back of the spatula. Transfer back to the medium bowl, cover with plastic wrap on the surface and refrigerate until chilled, at least 2 hours.
Step 4
Make the Whipped Cream: In the bowl of a stand mixer with the whisk attachment, whip the cream and confectioners' sugar to soft peaks.
Step 5
Assemble the Pudding Cups: Have ready 6 small ramekins, cups or jars. Spoon about 2 tablespoons of the pudding into each ramekin (no need to be too precise), then top with 2 or 3 Nilla wafers. Spoon about 2 tablespoons of the whipped cream on top, followed by a few banana slices. Repeat with another layer each of pudding, cookies, whipped cream and bananas. Garnish with crushed cookies, if desired. Refrigerate for at least 2 hours before serving.