I got a comment here that said,
Please omit the "Where have you been?" part of your social interaction. That is going to set me more on edge, not put me at ease. It sounds "stalker-ish", which is especially bad in OP's case where you look ragged.
and before that Strongbad had suggested changing
Where are you headed? to Where have you been?
for basically the same reason.
However, this doesn't match my personal experience at all. In my experience if you are making someone else nervous, they are going to pass you quickly without talking.
On the other hand if you meet someone and are talking its seems very normal to discuss either of the questions especially for finding out what lies ahead if you are going opposite directions.
Is it actually badpoor etiquette to these questions?