In Monsey, Rabbi Israel Flam was a mechanech (YSV) and also sat on a Beis Din. We (my wife and I) had a Din Torah and he was very nice to us, also he was my daughters’ Menahel. So when he was niftar I went and his sons didn’t know who I was but I told them how helpful he was as a Dayan and they appreciated it.
I remember feeling awkward at shiva visits when I was young, but I think as you get older the awkwardness disappears.
I once was menachem avel by a great Rav whose wife died suddenly, he had just flown from Israel and then suddenly I was face to face with him, and the first thing I said was, “The baalei musar talk about the difference between shivron lev (being heartbroken) and dikaon (depression)” and similar things and the conversation actually was fairly smooth
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