Beat the Cream Cheese In a large mixing bowl, beat the softened cream cheese until completely smooth. Add the sweetened condensed milk slowly while mixing. Continue beating until the mixture becomes glossy and creamy with no lumps. A hand mixer works best here, but a sturdy whisk can also do the job.

Prepare the Pudding In a separate bowl, whisk the instant pudding mix with cold milk. Whisk for about 2 minutes, then let it sit for 3–5 minutes so it thickens properly. Make sure you’re using instant pudding, not cook-and-serve pudding.

Combine the Filling Add the pudding mixture to the cream cheese mixture and mix until smooth. Then gently fold in the whipped topping using a spatula. Fold slowly so the mixture stays light and fluffy. At this point, the filling should look airy, smooth, and thick enough to spread.

Layer the Dessert Use a 9×13 baking dish. Start by placing a layer of Chessmen cookies across the bottom of the dish. Next, add a layer of banana slices. Spread half of the pudding mixture over the bananas. Repeat the layers: Cookies Bananas Remaining pudding mixture Spread the top layer evenly to the edges.

Add the Final Cookie Layer Place the remaining Chessmen cookies on top. Arrange them neatly so the dessert looks decorative once chilled. Cover the dish with plastic wrap and refrigerate for at least 4 hours, though overnight is ideal.