Since starting to approach total strangers in New York City for street portraits for a couple of years (coinciding with Covid international travel restrictions), I've been meaning to write up my thoughts about my experiences and tips.
I estimate my 'success' rate in photographing total strangers in NYC is 95%.
First off, it's important to differentiate the act of approaching strangers for street portraiture in a foreign country and New York City. Depending on the country, it can be extremely easy (as in India, as one example) or very difficult (as in Morocco and others)...cultural norms vary from one to the other so as photographers, we have to be sensitive to them. In New York City, it's not difficult although one has to be aware of many factors.
My experience can be distilled as follows:
1. Two critical things to start off with are (a) my appearance/demeanor as a photographer, and (b) the location of the approach. I always make a conscious effort to look the part, to look neat and to impart my professionalism. I don't want to sound too cocky nor too humble...just being myself is the goal. I often carry two cameras; the XPro2 (or 3) rangefinder dangling from my neck, and the medium format GFX50R in my hand. The visible gear conveys that I'm a serious photographer.
The choice of location is equally -if not more- critical. Most of my street portraiture is done in Washington Square Park, where people congregate in large numbers and are used to photographers of all stripes taking pictures. In fact, some of the people I met come to the park to be seen and often expect to be photographed as well. Call it what you will, but that makes the approach much easier.
A public space like the park is important because it's safe....there are people milling about, and it's a safer environment than other less frequented areas.
4. And here's another must do...I always show the persons the initial photographs on the camera's LCD within the first 2-3 minutes of the photo session. The GFXR camera has a very large screen, so they're invariably glad (and impressed) by how high the quality is. It has always been my experience that once they view the initial photographs, they relax. Notwithstanding, I continue showing them subsequent photographs so they continue enjoying posing. This establishes a mutual trust and is a win-win for both of us.
5. Whether I engage in a conversation post-session with the person I photograph largely depends if the mood is right for it. I avoid personal questions, but I've experienced showing an interest in their background, in their names or their heritage is appreciated. In such cases, I share my own background and heritage...and how to pronounce my name. In almost all cases, it's never "cut and run" unless I feel they need to go somewhere else.
6. And for the clincher...earning the respect and trust (professional and personal) of the persons I photograph in the way I comport myself during and after the initial session often leads to other opportunities, such as setting up more than one-on-one photo shoots in the streets of SoHo and elsewhere.