How does this sort of conversation transpire in Japanese? I guess its not a real apology in any sense, but more of a verbal expression of sympathy. Although it could be an apology for bringing up the topic, but in my experience I don't see that sense as the most common usage. Rather, it seems just a reflexive expression of sympathy, or what have you. I know the Japanese are a superstitious bunch, so maybe they generally avoid speaking of the dead, but I'm sure there exists at least one appropriate phrase that corresponds to what we say in English.