A 13-year-old found out. This story is a month old, but I just came across it. BBC NEWS | UK | Magazine | Giving up my iPod for a Walkman. Among his amusing observations:
It took me three days to figure out that there was another side to the tape. That was not the only naive mistake that I made; I mistook the metal/normal switch on the Walkman for a genre-specific equaliser, but later I discovered that it was in fact used to switch between two different types of cassette.