This problem has plagued me for years. The problem is that some of my contacts have switched email addresses (or I once typed in their email erroneously) and the old emails keep popping up in my gmail. I can't seem to remember which is which (old vs new) so I'm constantly having to look it up or risk making mistakes.
This has turned out to be a very sensitive issue in the case of one attorney that I work with who switched firms. But his address at the old firm pops up and I'm worried about sending sensitive stuff to the wrong law firm. And the actual emails are obscure lawfirms names like: ibsolaw.com vs aobtlaw.co (ibsen, broderdick, and ostrich law partners). I have the same problem with our book-keeper.
Solution: Click in Gmail on Contacts. There are three groupings. "my contacts", "most contacted", and "other contacts". I found the problems under other contacts and removed it.
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