Whisk cold milk and pudding mix in a large bowl until smooth.
Chill for 30 minutes.
In another bowl, beat sweetened condensed milk, cream cheese, and vanilla extract until smooth.
Fold in Cool Whip.
Fold the cream cheese mixture into the chilled pudding.
In a 9x13-inch dish, layer one-third of the whole wafers, half of the crushed cookies, and one-third of the pudding.
Add half the banana slices, then half the remaining whole wafers.
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