This will fit in a 6-inch or larger trifle bowl OR you can also make it in a spring-form pan and unmold after a night in the freezer; it will stand. You can pretty much use whatever type of bowl you would like as long as you make it the night before and refrigerate to allow the cookies to soften and the flavors to blend.
Mix the milk and Kahlua together. Dip each cookie in the Kahlua-milk mix (just a dip, no need to let them soak) and line them along the bottom of your dish. Spread a thin layer of Cool Whip on top, then dip more cookies and layer them on top of the Cool Whip. Repeat, alternating layers of cookies and Cool Whip until you reach the top or use up all the cookies and Cool Whip.
Fancy it up with a sprinkle of grated chocolate and crumbled cookies or a dusting of cocoa powder on top. Then gently scoop out servings onto individual dishes and admire the striking layers.
The partakers will form, cooing around the dish and trying to figure out what, exactly, is this wondrous looking dessert. It's sweet, of course, but there's a faint boozy bite as well. It is a tiramisu with...chocolate chips? A certain cookie-aisle 'je ne sais quoi' that you needn't explain to anyone :) .