Hi, Ziploc. While I am not an expert (been doing street photography only about a year), I'll try to answer your questions here.
First, visit a few websites to get inspired. I was basically inspired to get into street photography after visiting websites like:
and of course our very own Singaporean,
After being suitably inspired, just go out and shoot lah!
On the one hand, you want to shoot candid photos. This means that the subject must not know that he is being photographed. I think, above all, your motives must be pure. There is an element of voyeurism in street photography - you want to capture glimpses of life in its raw, natural form. There is sometimes only a fine line between that and being a cheekopeh. For this reason I seldom take pictures of young women. Anyway there are enough of such pictures floating on the net. I prefer character studies of old folks and foreign workers. You will see this as a theme in my work:
On the other hand, you can get very nice smiles and portraits if you just ask for permission. You don't even have to open your mouth for this. Most of the time, what happens is that I try to get candid shots. If I am spotted, I just nod and smile in a friendly manner, and point to my camera. They will usually oblige and pose for me, or smile nicely, like this satay man and this car washer. The satay man saw me taking pictures of him through a fence and challenged me, asking what I was doing. I said I was taking photos, as a hobby. He smiled then and continued working. Now, the picture of him is very attractive, so I don't see why he would object to it.
I've only once asked verbally if I can take pictures, and the result was a very stiff portrait, which I won't bother to show.
(to be continued)