So, Gmail does NOT...

NetDude

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... have a default email address functionality? :( I have a few contacts groups and would like to be able to specify, in a particular group, which of Bob's email address I would like to send a particular mail.
(I hope the question makes sense.)
 
Yeah it does under your account settings. I have about 20 email accounts tied to my gmail, and my default reply-to address is not a gmail address.

Click settings -> Accounts and import
 
... and my default reply-to address is not a gmail address.

:) Thanks.
Let me rather paint a scenario: I have got a friend, let's call him Bob. He has got two email addresses: private and work. I have created two contact groups in Gmail: "friends" and "colleagues". I have added Bob to each of those groups. There are certain mails I would like to send to Bob's private address and other emails, of different nature, to his work address. Gmail SEEMS to always send email to the email address listed FIRST when creating a contact.

/hopes that this is clearer.
 
I think Gmail defaults to the first address in the contact list so you might have to rearrange the order they're listed in? Pity Google Labs doesnt seem to have a solution.
 
Just create two seperate contacts for Bob... one with his work address and one for his private address. Like this....

Contact 1: Bob Smith (Work)
Contact 2: Bob Smith (Private)
 
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