Maybe you've also heard it on This American Life. A woman was talking about her relationship with his boyfriend who had dumped her and that she had starting to write his number on bathroom walls "across the United States", so that people would call and tell him that his 'chilouppa' really missed him. I couldn't find a word pronounced like that except 'chalupa'. Now if it's a term of endearment as well, how could it be related to the other meaning- kind of a fried corn? Is it somehow like what we, Iranians, say- I like it so much so that I like to eat it?
I found a transcript of the TAL episode you're referring to.
In this transcript it is spelled "Chalupa".
People make all kinds of words into terms of endearment. I've heard stranger.
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