Reader Matthew Rotter asks a common question about Apple's Mail. He writes:
Can you send email to multiple email addresses listed under a single contact's name?
Pardon me if I assume that what you really mean is whether it's possible to easily add to an email messages multiple address from a single contact. And the answer is, not really. Regardless of the solution you settle on, it requires a bit of futzing. Now, let's go over those solutions.
The first is that for those contacts for whom you routinely use multiple email addresses, create a new contact card for that individual and in the first email address field, enter multiple addresses separated by [email protected], [email protected], [email protected], for instance. Add this contact to a message's To field and the message will be sent to all three addresses. (You're welcome to edit an existing contacting rather than creating a new one if you like.)
Next, you can create separate contacts for each address--Joe at Home, Joe at Work, and Joe at Play, for example--and add those contacts to a group called All Joe All The Time. Send a message to that group and Joe will get it wherever he may be.
Or if this is the kind of thing you very rarely do, create a new email message, choose Window > Address Panel, and in the resulting Addresses window, search for your contact. All of the email addresses associated with that contact will appear. Individually double-click the addresses you'd like to send the message to and they will appear in the To field.