This does seem, well, screwy. Certainly AA's posted procedure does and has applied for all the flights I have been on (quite a few) that I know of. I don't know how specific the system is, but my understanding is that it goes all the way back to "minute" of booking when searching for the upgradeable peoples. Assuming both of you just bought the same ticket (no holding), and you bought first and requested first, I think we just have to boil this one down to an IT problem. That, of AA's system was smart enough to figure out that you would rather have your significant other upgraded in front of you anyway
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