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I started hearing this word in various anime: it's starting to seem quite common, but I'm not sure about its meaning.

Jisho lists it as "sincerely; repeatedly", but it doesn't seem to be it's whole meaning, if at all; unfortunately I wasn't able to find the examples where I heard it in the past, but I took a couple from Jisho and one from the last time I heard it:

明日からくれぐれも頼んだよ

We are counting on you from tomorrow

あの方にくれぐれもよろしく

Give him my best regards

くれぐれもお体をお大事に

Please take good care of yourself

くれぐれも気をつけてください

Please be careful

It seems to me in those examples it doesn't really translate as per Jisho: if it's translated at all (in the first example it doesn't seem to be translated), it in "best regards" and "good care".

I tried Weblio, but as far as I can understand it says it means "To repeat many times; used when asking sincerely", which seems more or less in line with Jisho and again doesn't seem to really fit.

Am I right in thinking that 「くれぐれも」 is best understood as an intensifier, a word used to put emphasis on what is being said, rather than having specific meanings like those given by Jisho? If I'm right, 「明日からくれぐれも頼んだよ」 wold mean something like "We are really counting on you from tomorrow", "We are counting on you from tomorrow [and we are expecting results]".

(Also, I'm just realizing this while finishing this question, I'm not sure why with 「明日」 is used 「頼んだ」, a past form.)

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    Why do you count out the literal: "we sincerely ask you for the favour," "give them my sincere regards," and "I sincerely hope for your recovery?" – macraf Jan 29 at 20:11
  • For the first one "We are counting on you" suits the context better, but it could be read as "We are sincerely counting on you"; it does make sense, maybe I was focusing too much on the given translations instead that rephrasing them. Also I added another example; if I were to use "sincerely" as meaning it cold be something like "I sincerely ask you to be careful", but it sounds kinda awkward, reading it as an intensifier sounded better to me, but maybe it's just my translation? – Mauro Jan 29 at 20:26
  • I don't think くれぐれも気をつけてください is used for "please be careful", but rather "goodbye, take care". – macraf Jan 30 at 9:06
  • Unfortunately I don't remember where I saw that example, so I can't check the context; anyway, "sincerely" still sounds odd to me, also with your translation: "Goodbye, sincerely take care"? "[I sincerely say] Goodbye, take care"? – Mauro Jan 30 at 9:27
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I think you are more or less correct. くれぐれも is one of those most difficult words to translate from Japanese. In one phrase I would translate it as "be sure to", in the context of being an intensifier. This is a relatively "stronger" intensifier, as you may know Japanese has many words to strengthen a meaning, this one being on the higher end of the scale. Also, some words or phrases do not work with other intensifiers, may even only work with a specific intensifier. For example, I can't think of any other intensifier that works with 頼んだよ so the strong version of 頼んだよ would always be くれぐれも頼んだよ. However a similar but slightly version 頼みますよ can also go with しっかり. So since くれぐれも has quite limited use cases, using this phrase yourself is a bit more tricky.

Anyway, the short answer is, くれぐれも is an intensifier so all of the above phrases (in your question) become stronger or more sincere with the くれぐれも than without.

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