I had a girlfriend that was giving a birthday party for her five year old. She made chocolate chips cookies, but baked them in muffin tins. She waited until they cooled down before removing them from the tin. Then she took a scoop of ice cream and put one scoop in each cookie. She deliberately baked the cookies so that when cooled, they were crisp. Hmmm... I should give that a try. Sounds like the perfect holiday dessert. Not too filling and who doesn't love ice cream and chocolate chip cookies. I don't know why I haven't tried this before.
I have three different size dashers for the cookies. Use the large one for the cookie and a smaller one for the ice cream. I would want the cookies to be thick enough to stand up to the ice cream.