Try this:
Create a Group List named "Doe Group"
Create a Contact named John Doe with the email address
Create a Contact named Jane Doe with the email address (yes, same as above)
Add both Jane Doe and John Doe to the Group List named Doe Group
In your Contacts list double-click on Doe Group
Save the email to your Drafts folder
Close the email then re-open it from your Drafts folder
Now look at the "To:" field
There is only one name!

WHY ???????????????

I have husbands and wives that share the same email address and belong to the same Group List. I usually contact them individually on different subjects. This time I want them to each get a copy of the same email.

Whaz UP?!