In a medium bowl, with an electric mixer, beat heavy cream, milk, and banana pudding mix, starting on low, increasing to high until everything is whipped up smooth and fluffy. About 2-3 minutes.
Place each serving in a 5 oz cup. Add 3 cookies to the bottom of the cups, add 2-3 tablespoons of pudding, then repeat. (add additional bananas in each layer if desired)
Add a few slices of fresh sliced bananas pieces.
For whipped cream: In another medium bowl (or wash and rinse the bowl with cold water so the cream whips easily), add 1 cup heavy cream, and add the vanilla, and powdered sugar. Whip on high until medium peaks form.
Top each dessert with whipped cream, top with 1 more cookie.
Place in fridge for 30 minutes to overnight. If preparing the day ahead, place lids on top and refrigerate.
