Well I am married so I don't have the girlfriend issue, but I had a pretty prestigous job prior to webmastering, and I haven't even told my family what I do. I don't know how to even tell them, as I know my mother would fucking drop. But I don't know what is worse, as they all think I am a bum and just bike and play video games.
That is what really pisses me off, is that I, like most of you webmasters out there, work incredibly long hours and if I even got paid a tenth of what I used to make I would be happy, but thats another story.
I've always wondered what other webmasters tell people.