Prep the fruit: Wash and slice the strawberries. Slice the bananas just before assembling and lightly toss them with a bit of lemon juice to slow browning. Pat the fruit dry with a paper towel so the layers don’t get watery.

Make the pudding base: In a large bowl, whisk instant vanilla pudding with cold milk per the package directions. For extra richness, whisk in 2–4 tablespoons of sweetened condensed milk and 1 teaspoon vanilla extract. Let it set for 5–10 minutes in the fridge.

Lighten the pudding: Gently fold in about 1 cup of whipped topping to make the pudding creamier and easier to layer. Don’t overmix; you want it fluffy.

Crush the cookies: Place vanilla wafers or your cookie of choice in a zip-top bag and crush lightly. Aim for a mix of small chunks and crumbs. This gives better texture than a fine powder.

Assemble the first layer: Add 1–2 tablespoons of cookie crumbs to each cup. Top with a few slices of bananas and strawberries.

Add pudding: Spoon in a generous layer of the pudding mixture. Smooth the top with the back of a spoon so the next layer sits evenly.

Repeat layers: Add another round of cookies, fruit, and pudding. Leave a little room at the top for whipped topping and garnish.

Top and garnish: Finish with a swirl or dollop of whipped topping. Add a strawberry slice, a banana coin, or a whole mini wafer for a simple, classy finish.

Chill: Cover each cup loosely with plastic wrap or place them in a covered container. Refrigerate at least 2 hours, ideally 4–6, so the flavors meld and the cookies soften slightly.

Serve cold: Right before serving, check the top fruit. If anything looks less vibrant, add a fresh slice for a pop of color.