Q: What is the email etiquette in this situation?
I emailed my colleague who happens to have about 4 different email addresses. I used the one she was using a few months ago……but I have a feeling she doesn’t check that one anymore. I sent the email 2 days ago but I still haven’t gotten a response. Should I email her using her “primary” email account even though she asked a few months ago to use the other one? How long should I wait without sounding annoying/desperate in case she did receive the original email and is just thinking about what to write back.

A: Until everyone in the world realizes that multiple email accounts makes as much sense as multiple physical addresses, you have to work around everyone’s annoying tendency to open a new address at the drop of a hat. I would recommend sending an email to all of her addresses in a single email, that way she can see that you have no idea which one to send it to. If they complain that you sent it to an old address, ignore it and just pay attention to which one they prefer.

Email is so new that most people have no idea what to do in terms of etiquette. Best thing to do is just cover all of your bases.