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Step 1
Make the pudding layer: Add pudding mix to a mixing bowl. Place ice cream in a microwave safe measuring cup, and microwave for 30-40 seconds until the ice cream is just melted but not heated. Add milk to the measuring cup, and pour into the bowl with the pudding mix. Whisk for 2 mins until the pudding starts to thicken. Set aside and allow to continue thickening up for about 5 mins.
Step 2
Meanwhile, make the whipped cream: To the bowl of a stand mixer fitted with the whisk attachment, add heavy cream. Whisk on high for 1-2 mins until soft peaks form. Add powdered sugar and vanilla bean paste. Whisk on high for about another minute until stiff peaks form. Set aside.
Step 3
Assemble the cups: To a small cup (I use a 9oz Chinet plastic party cup), add 3 Nilla cookies. Top with about 2 tbsp of pudding. Top with an even layer of banana slices. Repeat those three layers. Finish with a layer of whipped cream. Garnish with one crushed cookie and one banana slice. Repeat with remaining 5 cups.
Step 4
Refrigerate for at least 1-2 hours before serving. Enjoy!