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When I chat using romaji, Japanese will always use si instead of shi, for example yorosiku instead of yoroshiku, siteru instead of shiteru. Do Japanese actually pronounce shi as si?

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It's the difference between Hepburn romanization and Wapuro romanizaton. Adults generally use Hepburn system for person names, signboards, posters and such (し = shi, づ = zu, じゃ = ja). But when they need to type ordinary Japanese sentences using romaji, they (almost unconsciously) use wapuro style because it's more efficient and unambiguous (し = si, づ = du, じゃ = zya/jya/ja). You don't have to type shi to get し when you can get the same character by typing si.

Please remember that wapuro style has nothing to do with pronunciation. That's just an input method, how they type hiragana/katakana on keyboards. Don't assume anything about pronunciation based on English alphabet.

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