Is there a way to "cherry pick" which contacts you want to send an email to and then have it go out through the Bulk Merge feature?

My client's CEO wants to send emails periodically to a select group of contacts.  That part is great when using the Bulk Merge feature and selecting the Group that was created for each of these contact groups.  The problem is when he wants to send an email to select people within a group.  At first, I thought he could just go to one of the contact records, go to Messages and click the Email button, then add the other recipients in the bottom area as CC's.  But the problem with this is that it doesn't personalize the message for each