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I noticed that Yoshiyahu HaMelech tore his clothes when hearing Torah ‘late’ (2 Melachim 22:11). Presumably, because he realized he had been ignorant of what the Torah said and he now realized he had many sins going back many years.

Is one permitted (or even obliged) to do likewise when hearing something spiritually/morally/ethically important years after it ‘should’ have been heard? I am referring to that terrible feeling of regret and despair that comes over one when hearing something that would have saved one much humiliation if heard much sooner.

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    Jewish king is [somehow] responsible for the whole nation, so his negligence and ignorance impaired others. And if so, we don't infer from kings to laymen. – Al Berko Apr 8 at 11:54
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Radak and Ralbag explain there that when he found the Torah, he saw the part about "God exiling you and your king off to a faraway land", and thus felt this was an ominous sign that the kingdom was doomed. (Metzudas David says something similar – no matter where it was rolled, he felt it was an ominous sign.)

But just learning Torah and going "gee I wish I'd heard that earlier?" Hey, we all want to keep learning! (In fact, please don't tear your clothes, it's bal tashchis.) We don't find, for example, any reference to rending garments when the-fellow-later-to-be-known-as-Rabbi-Akiva had his epiphany and ran off to yeshiva, or during those yeshiva years. If the Sanhedrin (high court) or Kohen Gadol errs in ruling, they bring a sacrifice, but again, nothing about tearing their clothes.

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