Hehe.. He couldn't hit it cause his skill in the weapon he was using is not high enough yet. Each weapon type, long swords, short swords, etc., has a skill level ranging from 5 at lowest to 100 which is highest. When your skill level in a weapon type is below 20, the chances are slim for a successful strike. This will also be changed in Oblivion. In Oblivion every time you swing your sword, axe, whatever, it will make contact with your opponent, but the actual damage of the attack will increase as the weapons skill level increases.