Manually send an attached file to a contact

Situation:

• Each row of my sheet represents a different client's order and has that client's email listed in a contact-type column called, "Main Contact"
• At some point in the process, I need to manually email just one of the many attached files in the row to the Main Contact. I do NOT want to send all the files.

Question:

Is there a way to easily select the user from the Main Contact column to email this file? When I click on the "email" link from the attached documents area, there doesn't appear to be an option for this, which seems odd. Seems like there should be a way to choose one or more contact columns when manually sending a file, just as you can do when setting up an automated notification.