Comment by angiolillo

> It's fine to start a conversation with a women wearing headphones, just take it in stride and don't be weird about it if she isn't interested in talking. I do this (with men and women) a lot.

Not sure where you're from, but where I live, headphones are a well-understood signal that someone would rather not engage in conversation at the moment. Some have been conditioned to placate the kind of people who deliberately ignore these signals by engaging in brief small talk rather than risking a confrontation, but this shouldn't be misconstrued as an interest in talking.