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I can add me@mydomain.com under "send mail as" email address in Gmail settings.

But can I choose between two different names to use with it, like I can in e.g. Mac Mail?

For instance, can I set it up so when emailing I have the choice between sending mail as either Bob <me@mydomain.com> or Agent Black <me@mydomain.com>?

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Unfortunately, no.

However, if you're willing to use "plus addresses" you can mostly fake it.

Add a new "send as" address with Name of "Agent Black" and email address of "tog22+agentblack@gmail.com". (Obviously you'd use your own email address.)

When receiving mail Google will ignore everything between the + and the @.

I used to do the same when my kids were little to fake mail to and from their grandparents.

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    In addition, you could set the same "Reply-To" for both. – MrWhite Nov 7 '15 at 20:23

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