In all the times I have been out observing I have never had a bad experience. Everyone, be they drunk or rough looking or anything, has just been fasinated and wanted a look through the scope. Even the people that once were doing a major drug deal in a parked car came over for a look and were extremely friendly (Only once see a drug deal while out though
). For some reason when astronomy is involved everyone is friendly and interested. I would still recomend observing with a friend because it is always nicer to share the observing experience
.