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I know that -な can be used as a negative imperative when attached to the dictionary form. This is nothing new to me and it is taught along with other verb forms. Recently however I have also heard -な being used as an imperative when attached to the ます-stem in the same way that -て is used for requests. I assume it is a shorter version of なさい. As an example, I have heard the phrases 止めな and しな multiple times.

I don't remember hearing this back when I lived in Japan a few years ago. Has this use of な become more popular in recent years, or have I just first started noticing after my Japanese level has improved and/or me going from using Japanese in a real-life environment to in an online environment?

Also, what connotations does this use of な have? I assume it should be avoided in polite/formal speech, but is it rude, bossy, gendered etc?

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For the grammar and pronunciation of this pattern, please read my previous post here: Is the word 「やんな」positive or negative?

As for how old the patterns like 止めな/しな are, I can say they've been used for at least dozens of years. For example, in the film Castle in the Sky (1986), there's a famous line where an old woman says "40秒で支度しな" (Get ready in 40 seconds!).

They wouldn't feel out of place when used in rakugo or films set around the World War era. Although I don't have authoritative information, I suspect they emerged as colloquial slang around 200 years ago or so. Today, they're recognized as very casual usage, so they're mainly used when speaking with close friends or family members.

Compared to 見て (which is a casual request), 見な does give a somewhat forceful nuance, like you're giving a command or strong advice. But this doesn't mean it's rude or bossy as long as it's used appropriately. While it's used regardless of gender, it has somewhat of a masculine tone, so ojōsama-type characters in anime don't use this.

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な when following the plain form of a verb is the plain blunt negative imperative.

な when following the ます stem of a verb is the plain not-so-blunt positive imperative.

Expanding on that, I say "not-so-blunt imperative" to contrast with the actual imperative conjugation of a verb, which is the blunt imperative. Things like しろ・せよ ("do!"), 飲め【のめ】 ("drink!"), 食べろ【たべろ】 ("eat!"), etc.

The な after the ます stem of a verb is a truncation or contraction of なさい. So if you hear 止めな【とめな】, this is a shortened form of 止めなさい【とめなさい】. If you've learned the use of なさい, you've learned that this is used to express a soft imperative or strong request. This な has the same meaning, with additional overtones of informality / closeness due to the contraction.

Be careful in your listening. 😄

  • 止めるな【とめるな】 = "don't stop!"
  • 止めな【とめな】 = "stop!"

Timing

Adding on a note about when this form appears. If the 日本国語大辞典【にほんほくごだいじてん】 entry here at Kotobank (sixth な entry down) is correct, this contraction of なさい is attested since at least the early 1800s, in line with naruto's mention of a rough sense of 200 years of usage.

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    Also, answering the question in the title, I'm pretty sure this is a fairly old construction
    – Angelos
    Commented Nov 25 at 23:31

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