Place the shortbread cookies in a plastic zip top bag and crush using a can or
rolling pin.
In a bowl, combine the milk and instant pudding and mix well. Using a stand mixer
or hand mixer, combine the sweetened condensed milk and mascarpone and beat
until smooth.
In a separate bowl, whip one cup of heavy whipping cream to soft peaks and then fold
into the mascarpone mixture. Combine the mascarpone mixture with the vanilla
pudding and mix until smooth.
In the same bowl used to whip the heavy cream, whip the remaining cream with 2
tbsp of powdered sugar until stiff peaks form.
Using 8 oz mason jars, sprinkle about a tablespoon of shortbread crumbs on the bottom
of the jar. Next top with 4-5 slices of fresh banana and then 1 heaping
tablespoon of the pudding (I use a cookie scoop to do this). Repeat layers once
more and top with sweetened whipped cream, some more cookie crumbs and a sliced
banana.