As far as I know, the built-in email merge is very limited, where you can only send to one recipient at a time. So you'd have to put your 'pairs' actually on separate rows, and they'd get separate emails. Your actual template would be done in Word, and you then load your data in there, add the merge fields from your data, and then send the email merge through Word; FYI it will only send from your default Outlook email account. Hope this gives you some direction