Combine the cream cheese and Cool Whip in a mixer. Add the milk and pudding packages. Add the vanilla. If it seems too thick, add more milk until it reaches the desired consistency.
Use a round bowl and layer one third of the vanilla wafers on the bottom with a layer of bananas on top. Add the pudding mixture and then repeat the layer. Add the final layer of vanilla wafers to the top of the pudding. Letting it sit for awhile before eating will allow the cookies to soften.