I've discussed a few times in the past that the root חרט means "to engrave", as in the word charita חריטה - "engraving, chiseling." But I didn't answer the question: is that root related to the words charata חרטה - "regret, remorse" and hitcharet התחרט - "to regret"?
This meaning isn't found in the Bible, but first appears in Rabbinic Hebrew. Jastrow makes the fanciful suggestion that "to regret, feel sorry" is to "scratch one's self." Ben Yehuda says that the etymology of charata (and the related verb) is unknown and no cognates are found in Semitic languages.
However, Klein does provide an etymology. He has two distinct entries for חרט. After the entry for חרט - "to chisel, engrave", he has חרט as "to repent", and says that it comes from the Arabic inḫaraṭa - "he did ignorantly."
This would make it cognate with a common word in Israeli slang - kharta חרטה. It means "nonsense, rubbish", and I actually thought it was a rude word with scatological origins. But no, it just comes from the same Arabic root meaning "lies, nonsense." Related slang words are kharta barta חרטה ברטה - "nonsense, make-believe, baloney" and the verb khirtet חרטט - "to make up nonsense."
Going back to the original question, I expected some linguistic proof that the two forms of חרט are unrelated. This happens not infrequently with words including the Hebrew letter chet. While Hebrew has only one chet, the cognates in Arabic have two different letters - like a hard chet and a soft chet. So sometimes two words in Hebrew will seem to be homonyms, but when compared with Arabic, they will be shown to be unrelated. This was the case, for example, with the words for fat and milk - chalav and chelev. They are spelled the same in Hebrew - חלב - but are unrelated.
But both meanings of חרט have Arabic cognates, and both are spelled with the hard chet. So that can't prove they aren't related.
And in fact, while I don't have direct proof, I think that perhaps they are connected. Let's look another Hebrew root with similar meanings - פסל.
One meaning is "to hew, hew out, carve." From here we get such words as pesel פסל - "carved image, idol" and pesolet פסולת - "chips, stone dust."
The other meaning is "to disqualify, declare unfit." This meaning gives us pasul פסול - "disqualified, defective, unfit." For this sense, Klein provides this etymology:
Aram. פְּסַל (= he disqualified, declared unfit), Arab. fasala (= was ignoble, was valueless). According to several scholars פסל ᴵᴵ represents a special sense development of פסל ᴵ (as if פסל ᴵᴵ would have meant orig. ‘was cut away’, whence arose the meaning ‘was considered useless’). They refer to the sense development of פּֽסֹלֶת (= chips, stone dust), whence ‘worthless matter’. However, according to others פסל ᴵ and פסל ᴵᴵ are two different bases.
So according to the first explanation, which seems reasonable, there was a development from "carving" to "worthless matter." Could the same have happened from charita - "engraving" to kharta - "nonsense" to charata - "regret"? Doesn't look like kharta barta to me...
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