Whisk together the milk, pudding mix, powdered sugar (if using), and vanilla extract in a bowl until smooth. It should look like a glossy, sleepy lava lamp—no lumps allowed.
Let the pudding set in the fridge for about 5 minutes while you prep the fruit. This gives you a moment to feel like a magician without actually pulling a rabbit out of a hat.
Slice the bananas into thin rounds. If you’re worried about browning, a quick toss with a squeeze of lemon juice helps—but no drama if you skip it.
Beat the cream until it holds soft peaks. Fold it gently into the pudding for a light, creamy texture. If you’re using whipped topping, fold it in rather than beating it—let the laziness win.
Layer in a serving dish: cookies on the bottom, banana slices on top, then a generous swirl of pudding. Repeat until you run out of everything, finishing with a pudding layer.
Chill for at least 2 hours (or overnight) so the flavors mingle like old friends at a reunion. Serve cold and enjoy the compliments that follow.