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In a couple of the groups I belong to, several members use multiple email addresses. Sometimes two or more people use the same address. Even though I have each email address for each person listed in my Gmail Contacts list, Gmail defaults to one of the multiple addresses. I can't force it to choose any of the other addresses. There is no drop-down list of alternate emails for a single individual - though there is a drop-down list for all contacts whose last names begin with the same letter, for example. The only way I can get my email to the intended address is to go to my Contacts list and select the address from there.
I too have contacts who have more than one email address.
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I used numerals to make the identities separate "Mary 1" for business - "Mary 2" for academic and so forth. I'll try using the actual words "business" and "academic". Maybe that will work. Still, it seems a bit lame that Gmail can't give us a workable dropdown list.
I guess this is just part of Gmail. I'm surprised that nobody else has found it troubling, or that nobody has figured out a workaround.
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"Mary's" business address may come up today, but tomorrow all I can get is her university address.
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Maybe that's because many of us (if not most of us) don't seem to have that problem?
I wonder if you are being served by different Google servers that are not all programmed the same or do not have access to the same personal records for you. Though I've never seen (nor heard of) that before. That kind of thing happens with Yahoo, but I've never seen it with Gmail.
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The thing to remember is, Gmail is essentially a bunch of code running on top of a web browser, an app if you will. It stores a lot of this code offline for efficiency, instead of loading the full code every time.
It is more likely that this offline cache on your browser is corrupt than the Google code itself being broken for only a few users out of 26+ million.