Whisk together pudding mix, milk, and yogurt. Stir in dates and bananas.
Layer 1/4 cup of pudding in the bottom of each of four 8-ounce dessert glasses. Sprinkle 2 Tbsp cookie crumbs on top of each. Layer in another 1/4 cup pudding and another 2 Tbsp cookie crumbs. Top each with the remaining pudding.
If desired, garnish with additional dates and mint sprigs just before serving.