text: when the dentist drills how does it feel? i have never had a cavity in my life and i might have one.....i no they give you a shot but how does the drilling feel? if you are numb, it's weird.  you might feel the cold air and you will sense the fact that something is touching your tooth, but it doesn't hurt.  if your leg ever fell asleep and you tapped on it when it was good and numb, that's kind of the same sensation.