To the clean stand mixer bowl, add the softened cream cheese. Whip until fluffy. Add the sweetened condensed milk to cream cheese. Beat until smooth, scraping the bottom and sides of the bowl a few times. Add the dry pudding mix and mix well. Slowly pour in the milk and continue to mix until combined.
Add 3/4 of the fresh whipped cream (OR 1 container of Cool Whip) to the pudding mixture. Gently fold it in until fully combined. Set aside.
Place one even layer of Nilla wafers on the bottom of the prepared baking dish. Top the wafers with one layer of sliced bananas. Spread only half of the pudding mixture evenly over the top of bananas and wafers.
Repeat another layer of Nilla wafers and sliced bananas. Top with remaining pudding, spreading out evenly. Spread the remaining whipped cream (OR 1 container of Cool Whip) evenly over the top. Cover and place in the fridge to chill for at least 6 hours or overnight.