In a large bowl, add the cold milk, Dulce de Leche and mix. The mixture will be slightly clumpy. That’s okay. Sprinkle vanilla pudding mixture over the top. Whisk together until smooth. This will take 2-3 minutes. I prefer a hand whisk not a hand mixer because it will get clump. Let it sit for 5-10 minutes to thicken up. While it sets, beat the heavy whipping cream.

In a bowl of a stand size mixer or white an electric hand held mixer, add the heavy cream and vanilla extract. Beat until stiff peaks form to make whipped cream. If you over beat it, add a dash more of cream and beat until stiff peak.

With a rubber spatula, gently fold in the whipped cream into the pudding mixture. Set aside in the fridge for 1 hour.

To assemble, you can use individual cups, a large casserole dish, or a trifle bowl. Start with a layer of pudding on the bottom, then add a neat layer of whole cookies, followed by a layer of sliced bananas. Repeat until you run out of ingredients, aiming for 2–3 layers total. Finish with a final layer of pudding that fully covers everything, making sure to seal the edges so the cookies don't dry out.

Gently wrap with plastic wrap and allow it to sit on the fridge for at least 6 and up to 24 hours to soften up.

Take over what’s left over the cookies and just smash the cookies so there are somewhat bigger pieces and crumb. Spread that over the top. Garnish with more banana’s!