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Need some help with American English. When does one call a 44 year old man a "boy"?

I am not American however in my opinion calling a 44 y.o. a boy would be intentionally demeaning/insulting....unless the person doing the calling was older (perhaps a relative?) and then it could be considered affectionate

Perhaps also if the 'boy' is a servant or considered to be of lower rank or even race.

As an American, I second Stewart's comments. At least in the movies, the race scenario would be the most common.

Yes. If it's said to am adult, it's an insult in almost any case, possibly excluding a relationship on the part of the speakers; it's common, for example, in M/M BDSM or leather relationships, and even then it's clearly meant to imply that the speaker is above or superior to the person he's calling that.

If it's a white man speaking to a black man, it's also a racially charged insult.

its widespread use by US whites in the way that SamanthaJoy describes is in fact the reason that many male US civil rights marchers and protesters in the mid 1900's carried signs reading "I AM A MAN"

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Real easy, but a little slow while sleepy. 14.

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