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A friend is a teacher and regularly writes to her pupils' parents about their children. Thus she has Gmail contacts set up with a record for each child that contains the e-mail address of one of their parents.

Problem arises when she is teaching siblings. In the To: field she might write [Child2]. Gmail notices that [Child2] has the same e-mail address as [Child1] and thus the e-mail goes out as "Child 1" <email@address.com>. This makes it look unprofessional, like she cannot tell the two children apart.

Gmail, of course, allows you to record chidren's names within the parents record, but then you can't autolookup.

A related problem that I have found the solution for elsewhere in this site is when she wants to write to both parents. Seems the answer is to capture the e-mail address as "mum@parent.com>, <dad@parent.com". Strange but effective.

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[Not an answer per se.] I believe that her approach is flawed and this issue should be tackled using the subject field or the email’s body and not the address. (E.g. Subject: regarding Child 2 or the first line of the email’s body: This message regards Child 2.) –  Alex Sep 24 '13 at 14:59

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I would tend to agree with Alex in comments. Gmail does seem to get a bit confused when autocompleting names/emails when there are duplicates.

However, a possible workaround... instead of typing the name in the To: field and using Gmail's autocomplete, click on the To: instead to get a popup of available contacts (with a search box). Then select the appropriate contact from the list.

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W3d: Thanks, but I'm not sure this does adequately work around the problem. Put yourself in the scenario - thinking of a child and not necessarily at the time recalling that this specific child has a sibling. The child's name drives the selection of the e-mail address, which GMail then overwrites with the other child's name (albeit still with the same, correct e-mail address). Perhaps recording the name in the format 'Child1 & Child2 Surname' and then also listing the specific child in the e-mail title. Seems clunky and I wonder if there isn't a better way. –  andybjackson Sep 24 '13 at 17:41
    
Thinking about this again... you are sending an email to a parent about one of their children (the subject) - trying to incorporate this information into the To: field would indeed seem to be wholly incorrect, as @Alex has already suggested. Most email clients do not even display the To: field by default - so the information is going to be lost. Gmail, for instance, only displays the To: field if you open the email, but even then it is not complete... to see the To: field you need to click the down arrow to "Show details". The email subject would seem to be the logical and only choice. –  w3d Sep 24 '13 at 18:59

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