In a medium saucepan, whisk together the vanilla pudding mix and whole milk, stirring constantly for about 2 minutes until the mixture is smooth and well combined with no lumps. Remove from heat and stir in the light cream and vanilla extract, which will add richness and deepen the flavor. Let the pudding sit undisturbed for 5 minutes to thicken slightly—this is crucial for achieving the proper texture that holds its shape when layered. While the pudding rests, slice your bananas into 1/4-inch rounds; I find that uniform thickness helps them distribute evenly through each layer and prevents mushy spots.

Divide your assembly between two ramekins or small bowls. Start with a thin layer of 3-4 vanilla wafers on the bottom of each ramekin, breaking them as needed to fit. Spoon about one-third of the pudding mixture from Step 1 over the wafers, then arrange half of your banana slices evenly over the pudding layer. Top with another layer of 3-4 wafers, then add another third of the pudding. Finish by arranging the remaining banana slices on top, followed by the last of the pudding, and crown each ramekin with two vanilla wafers standing upright or laid flat. I like to reserve my best-looking wafers for the top since they're what you see first—it makes the presentation feel more special for a dessert for two.

Cover the ramekins lightly with plastic wrap or leave them uncovered, then refrigerate for 20-30 minutes before serving. This chilling time allows the flavors to meld and the wafers to soften slightly while still maintaining some of their crisp texture against the creamy pudding. Serve cold directly from the ramekin for an elegant individual dessert presentation.