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I have some friends in China and I started to learn Chinese. Nothing serious but a few phrases here and there. Due to the time difference the conversation usually ends in one of us saying good night to the other. Rather than just always saying 晚安 all the time, I started to copy some of the things friends have said to me as a means of saying good night.

However I'm thinking there might be some nuance between these phrases that is lost on me. One time I said 安安 to a male friend and he seemed slightly offended and told me don't talk like a girl.

Could someone explain to me if there is a difference between these and if so what the connotation of each one is?

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晚安 is the standard phrase for "good night"

晚安安 is an incorrect usage of reduplication. Please don't use it.

安安 is also an incorrect usage of reduplication. Not to mention it sounds like a 'baby take' (omitted 晚 and reduplicate 安) Please don't use it to any adult.

晚安啦 is just 晚安 adding a final particle after it. Depend on the tone and pitch, it adds casual or affectionate feeling to the phrase

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晚安 has no emotion.

晚安安 is indeed an incorrect usage of reduplication.

but 安安 is not an incorrect usage of reduplication. A girl can use this when she talks with her boyfriend to show intimacy. Yes, it sounds like a baby but that is how people show intimacy in China (maybe some Chinese, including my ex and ex-ex... girlfriend).

晚安啦 indeed adds casual or affectionate feeling to the phrase. It might also has implicit meaning "maybe we can continue our talk tomorrow night"

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晚安 and 晚安啦 are almost the same, and means "Good night". 晚安啦 may sound more casual.

晚安安 and 安安 can be considered Internet slang just to make it sound cute.

As a learner, you can stick to 晚安. I seldom see 晚安安 or 安安 even on the Internet.

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You should know that in oral Chinese, there is no standard grammar. Actually all the above are correctly phrases for "Good night". We can even just use single character 安 for it.

However, different phrases have different background meanings.

晚安 is the standard phase in both oral and written Chinese.

The other 3 phrases are most likely used within close friends/relatives, boy/girl friend.

晚安啦 is only used in oral Chinese, 啦 is a modal particle which is used when the speaker want announce some thing happens. 晚安啦 therefore more likely meaning the specking is happy to talk with you and want to announce the conversation needs to be stopped.

安 is used only with friends/classmates because it is an informal and impolite to speck, especially toward elders. Others might think this phrase is too concise to be respect them. However, it is very nature to use it with your best friend.

晚安安 and 安安 are very informal. It could be only used by girls or young woman. Or wife towards her husband. 安安 is sounding somewhat childish, the specking is playing cute/showing moe.

Young Chinese people do not likely the formal way to specking Chinese, they sometimes want to specking short/specking strange just to make fun. Therefore, nowadays people may more likely to use 男票/女票 to replace 男朋友/女朋友, just sounding shorter and more interesting. However, as a foreigner, you'd better take care for these phrases.

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