Your cookies really need to cool properly after removing them from the oven otherwise they can getsoggy and sad on the bottom, by placing them on a cookie rack you can avoid this because the heat can easily escape from the bottom and wont condense.
They need to easily soak up milk, but not get overly soggy too fast lest we end up with a tragic cookie - chunks - falling - right - off - the filling - into - the - milk situation.