Preheat the oven to 350 degrees F.
Cream together the butter, brown sugar and granulated sugar in a large bowl. Add the vanilla and eggs, mixing well. Combine the flour, instant coffee, baking soda and salt in a separate bowl. Add the dry ingredients to the wet ingredients in 3 batches, mixing after each one. Stir in the milk and semisweet chocolate chips.
Spread the mixture into a 10-inch skillet and bake until golden brown, 30 to 40 minutes. Remove the skillet from the oven, top the cookie with several scoops of your favorite ice cream, drizzle on some hot fudge and top with whipped cream and a cherry.