Sean Tucker is making some excellent YouTube photography content at the moment. If you haven't seen it, I recommend checking out his last video about photographing strangers with Gabrielle Motola. It gives a real insight into the process of approaching people, but also into the joy and possibilities that come with the experience. It immediately made me want to go out and take more street portraits (and visit Scotland again).
I was shooting some portraits with a friend last weekend and she asked how I'd use the images. I gave her a straightforward answer initially (maybe Instagram, maybe something to add to a portrait portfolio). But as we shot more I realized that my answer was missing the point. She was practicing some yoga and dance positions and the joy that it brought to her was obvious. Doing something she loved, that she had practiced and was familiar with, using the skills that she'd developed over years. And that's most of the reason why I was making the images. Not to have or own the photos. What I do with them doesn't really matter. It's to experience the photography, the interaction, the challenge, using familiar developed skills and hopefully taking them a little further.
I'm sure everyone has a slightly different approach to photographing strangers. I think one of the important ingredients is to know (and be able to explain) why you're doing it. But I also find that I'm less often asking for a portrait first. More often I'm just starting a conversation, being open to the interaction whenever the opportunity comes up, then asking for a portrait later. And the portrait becomes because I genuinely want to remember the interaction, to remember the person.
Some people say to photograph what you love and others to photograph what scares you. Portraits of strangers are a little of both for me. It's a constant challenge, it's uncomfortable, but I love the connections and interactions and stories. Not to try to be the new Humans of New York, but to meet people, get better at meeting people and get better at really hearing their stories.