Unless the person you’re asking to photograph on the street is a skilled model, they’re probably as nervous in being photographed as you are about asking. I haven’t been as successful at it as I would like but the times I have been, I like to think it’s the combination of expressing my intentions very well and offering a business card to legitimize my work that’s helped.
I love this series taken along Orchard Road, Singapore by Boong as a part of a small project for himself. His aim was to showcase 365 faces by the end of 2010. Photographs were taken with a Nikon D90 using a 50mm f/1.8. It’s never easy approaching complete strangers but once you become more secure with the fear that never really goes away, I can see this technique being addictive. Street portraits can be a powerful thing. Danny Santos is someone I applaud for this type of brave work.