In a mixing bowl, prepare the instant banana pudding mix by whisking it with milk according to the package instructions. Let it set for a few minutes.
In another bowl, combine the mashed bananas, sweetened condensed milk, and vanilla extract. Mix well.
If you're making adult-friendly shots, gently stir the vanilla vodka into the banana mixture.
Gently fold the whipped cream into the banana pudding mixture until fully incorporated.
To assemble the shots, start by placing a layer of crushed vanilla wafers at the bottom of each shot glass.
Add a layer of the banana pudding mixture on top of the crushed wafers.
Repeat the layers until the glasses are filled, finishing with a layer of pudding on top.
Add an extra touch of flair by garnishing with more crushed vanilla wafers or slices of banana, if desired.
Allow the shots to cool and set in the refrigerator for a minimum of one hour before you're ready to serve them.