I spoke with fighter pilot and instructor with a degree in aeronautic engineering.
Yes both planes produce a sonic boom. But how the boom impacts you is dependent on your velocity relative to to the boom. The boom is a single percussion wave. If you are traveling with it you basically slow it down - it takes you longer to get from one end to the other. It is like a boxer taking a punch. You can even take it out of audible range of a human ear. Even a single percussion wave has a frequency. The trailing plane entering and exiting the cone is aware as the pitot tube velocity goes out of whack but it is not that big a deal.
So for my direct question of do you "hear it". If it get taken out range of your ear then you don't hear it.
As for approaching the wave still has the same amount of energy but you experience it faster. It could get taken out of the frequency range of the human ear on the high side but you would be more aware as you took the hit in a shorter period of time.