2.Completely line a 2-quart mixing bowl with chocolate chip cookies that have been dipped in milk mixture until moist (see Tip). Cover cookies with a 1/2-inch layer of whipped topping. Repeat layers until all cookies are used, reserving 1/4 container of whipped topping. Cover bowl and freeze overnight.
3.Unmold by dipping the bowl in a warm water bath, making sure no water gets into the bowl. Turn onto a serving platter, remove bowl and plastic wrap, and cover with remaining whipped topping. Cut into pie-shaped servings. Serve immediately or cover loosely and keep frozen.
Test Kitchen Tip: Soak the chocolate chip cookies until they are soft, but not falling apart. Too short a dunk and they’ll be hard, too long of a dunk and you’ll have a mess. Trust us on this…we screwed up the first time we made this, so you don’t have to!