When I do street portraits. I like to shoot close ups.

I saw this man sitting on a bench at Jalan Masjid India. The first thing that came in mind was to decide if the subject was "worthy" to be photographed or not. I do not just attack randomly at anything and anyone on the street, you have got to be selective on your subject content, because only the subject content that managed to catch your attention, and attracted you in certain ways that will make an interesting photography subject. There was something rather inviting about the look in this man's eyes. I moved in closer, put the camera (E-5) on my face and snap a frame from quite a distance away, as a test/warning shot, to see what kind of reaction I would get. He saw me, and he noticed I was having a camera, already shooting him. He was still looking at me, and I put down the camera, looked back at him, offered the warmest smile I can come up with at that moment, and then nodded to him to acknowledge his presence. In that smile and nod, I sort of sent some telepathically embdeed message across telling him that 'I mean no harm, and I seek his permission to shoot his photograph". For some unexplained reasons, I was fairly certain that telepathy voodoo happened, and he got the message, because in return, he offered an equally, if not warmer smile, and nodded back, as if telling me that "hey, I am ok and you can take my photos!!". That was the cue and green light I needed, so I stepped in closer, standing about two meters away from where he was sitting. I composed him tightly, wanting just head and shoulders shot. I snapped a few clicks, chimped a little bit, and was satisfied with what I saw on screen. I smiled again to him, said "thanks", and he nodded. I walked away, happy with this shot you see above.
What made this photograph work was the direct eye contact, and the apparent permission which was granted, knowing fully his photograph was being taken. He did not exactly pose or fake a smile for me. Instead, amazingly he looked surprisingly natural, and that friendliness he has shown to me as I approached him in the first place was well captured in his facial expression. The warm smile, the inviting looks in his eyes. The brief connection, no matter how small and how insignificant it may be for a passer by, there was indeed a connection, and that connection makes all the difference. If he has smiled a little wider, he would have appeared too forced. If he did not smile at all, it would seem he was uncomfortable having his photo taken.
I also strongly believe that we have to watch the comfort zone of the street subjects. Getting in too close would have resulted in uncomfortable expression response, either shocked, or annoyed look in their faces. The worst that could happen would be someone giving you the "What the F***" kind of look, as if the fist would fly to your face next. Everyone has different comfort and safety zone, and it is not easy to recognize the varying comfortable working distances for each subject. However, if you get close enough to a lion's mouth, you might just get your head chewed off. So becareful !!
Do you shoot street portraits? Do share your thoughts !