Prep the fruit: Hull and slice the strawberries.
If they’re not very sweet, toss with a teaspoon or two of powdered sugar and let sit 5 minutes. Slice the bananas just before assembling. For extra insurance against browning, lightly toss banana slices with lemon juice.
Make the pudding: In a mixing bowl, whisk instant pudding mix with cold milk for about 2 minutes.
Let it thicken for 5 minutes. Stir in vanilla extract if using. If using homemade pudding, make sure it’s fully chilled.
Crush or sort the cookies: Leave some cookies whole for layers and lightly crush the rest for texture.
You want small chunks, not fine crumbs.
Set up a layering station: Arrange cups, pudding, bananas, strawberries, cookies, and whipped cream within reach. This keeps assembly quick and tidy.
First layer – cookies: Add a layer of cookies to the bottom of each cup. This creates a base that softens into a cake-like bite.
Second layer – pudding: Spoon a generous layer of vanilla pudding over the cookies.
Tap cups gently to settle.
Third layer – fruit: Add banana slices, then a few strawberry slices. Keep a few pretty slices for the top.
Repeat layers: Add another round of cookies, pudding, and fruit until cups are nearly full. Leave space for whipped cream on top.
Top with whipped cream: Spoon or pipe whipped cream over each cup.
Garnish with a strawberry slice, a banana coin, a cookie, and a mint leaf if you like.
Chill: Cover and refrigerate at least 1 hour so the flavors meld and the cookies soften slightly. They’re best within 24 hours.