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I've heard おいたん is "kiddy speak" equivalent to Uncle in English.

Does it have any specific connotations? (Certain parents older/younger sibling?)

If used jokingly what kind of feeling would it give to the person being called?

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I don't think there are any specific connotations. It can be any uncles (either parents, can be younger sibling, can be older sibling) but I can see that some people call a middle-aged man who is not related as おいたん.

If I hear/see a man being called おいたん by a girl, I'd think that:

  • the girl really likes (can be romantically or just as a friend) the man and kind of flirting/babying/being sweet/being very friendly
  • the man may be very popular and everyone calls him that way (I say this because there was male school staff (around 50 yrs old) at my elementary school and everybody called him おいちゃん whereas we were supposed to call him おじさん because he was very kind and nice to us and we all liked him. But I think おいたん sounds more like a kiddy speak because it sounds more like a baby)
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This only expresses kids that cannot speak right at the beginning of life.

They try to say おじさん, but the じ becomes い, and the さ becomes た, hence おいたん.

http://dic.nicovideo.jp/a/%E3%81%8A%E3%81%84%E3%81%9F%E3%82%93

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Semantically I think おいたん is exactly the same as おじさん, but I have never heard anyone say おいたん in the real world. In fiction, おいたん is sometimes used to exaggerate the childishness of a character. For example, according to Nicopedia, Uncle Jesse is called おいたん by Michelle in the Japanese version of Full House.

Just like English uncle, a おじさん refers to both younger and older siblings of both parents. But additionally, you can address a middle-aged male stranger using おじさん in Japanese. This is like English "buddy" or "mister".

I can't imagine how people would feel if you used おいたん "jokingly". Depending on your Japanese level, perhaps people will be simply puzzled for a while, and then try to correct the word. If you're lucky, maybe some people would ask you if you're a fan of Full House.

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