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I have recently stumbled across the word どうしたって which according to the dictionary means "by all means, no matter what, at any rate". I was wondering how its usage differs from 是非 "certainly, without fail" as they both have very similar meanings. Does one have a positive connotation and the other negative? Are they interchangeable or not? If anyone could tell me the difference I would greatly appreciate it.

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    Welcome Ethan! Though your intro and greeting were definitely well-received, I have edited them out because we tend to keep questions as brief as possible and to the point. But this is certainly a good question, and the type of content we enjoy around here.
    – istrasci
    Commented Jan 24, 2023 at 2:44

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You are close. These are used in different types of sentences.

どうしたって (or どうしても) is usually followed by something undesirable or inevitable.

  • どうしたって無理だ。
    No matter what, it's impossible.
  • 他人の気持ちを理解するのはどうしたって難しい。
    At any rate, it's hard to understand the feelings of other people.

是非 is an adverb that is used exclusively when you strongly invite or recommend something. I feel it's weaker than 必ず ("without fail"), though.

  • 是非パーティーに来てください。
    Please come to our party!
  • このゲームは是非プレイするべきです。
    You should definitely play this game.
  • 是非!
    Yes, please do! / Definitely!
    (after being asked whether they should do something)

(Note that both どうしたって and 是非 have other usages.)

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  • Does 是非とも carry any additional weight over just 是非?
    – istrasci
    Commented Jan 24, 2023 at 2:45
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    @istrasci 是非とも is simply stronger, but I think 是非 is usually enough. Overusing 是非とも may sound like a salesperson's talk.
    – naruto
    Commented Jan 24, 2023 at 2:49
  • Would you ever say 是非 with friends or is it mainly for polite speech?
    – OtheJared
    Commented Jan 24, 2023 at 5:42
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    @OtheJared 是非 is not particularly formal, but something like 絶対 may be preferred in slangy speech.
    – naruto
    Commented Jan 24, 2023 at 6:29

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