Sorry Chrisburke, perhaps I should have been not so generic in my posts.
My post is more a double-pronged situation in general.
1. I have the problem of feeling as though I'm being annoying, or might be offending people by taking a random shot of someone from close proximity.
2. I can do group photography, and I can do posed portrait photography, however I do get nervous when I'm trying to take a photo, however the settings need a bit of tweaking, or I want to experiment, and then the subject gets irritable because they have to hold the pose, or re-pose every time I look at the picture I just took, adjust my settings and reshoot. It's mostly when I'm trying to work out how much fill flash I want, and if I'm using an external flash if I want it to reflect off the roof or a wall.
From viewing the Bruce Gilden video, it helped in showing me how some people get those random photos of people doing things. They don't ask, they don't warn. They just take.
I don't want to do the same thing as him though. I felt the urge today, at lunch (though admitttedly the nervousness became a bit overbearing), however I didn't really see anyone interesting. Except, however, for a large girl in a red dress too small for her, black bike shorts, and bra in view. Going nuts at herself, and anyone else, whilst she paced backwards and forewards.
I thought I would take a photo of her, but then I had a hairdressers appointment, thought i might be taking advantage of her "problems", even so. I said I would photograph her after I got out of the hairdresser, and, as always, by the time i had left she was gone.
That's a typical me, missing an opportunity. Making excuses for other people for why I shouldn't take their photo.
I guess, it will get easy with practice and with continuously walking around with the camera.