June 2013, Washington D.C.
I rarely stop strangers to ask for a portrait. But back in 2013, I spent some illuminating weeks with photographers in the area – the guys at Strata Collective, Diriki Rice and John Nelson – learning about their practice, and was encouraged to step out of my shell. That time in DC remains one of the highlights of the last few years: for the fellowship, the broadening of horizons, and catching up with my very old friend Carmen, who put me up for the 3 weeks I was in town.
I stopped many strangers in that time, and often find myself thinking of the people I asked for a portrait. There was Shaun, below:
I was hanging around a corner in Washington DC’s Chinatown, when she walked by with a group of friends. We passed each other twice more that day before I plucked up the courage to stop her and ask if I could take a picture.
And this there was this lady, whose name I can’t remember:
I saw her waiting for a portrait at a session one of the Strata Collective photographers was running, at the Lumen8 Anacostia festival. I liked the logo on her tshirt, which I found out later, belonged to the No Kings Collective.
I have learned, in the 3 years I’ve been wandering around, to talk to strangers if they will talk to me. But I rarely make pictures of the people I have passing conversations with on the street. Once someone stops and gives me their attention, I’ve lost my intended frame. I am an observer by nature, and find inserting myself in a situation without cause, unnerving. I’ve been surprised at how gracious most people I’ve asked, are about having some random photographer take their picture. With all this suspicion directed at photographers in the last few years, I expect to get told off (which also happens).
The height of this new found mode of operation happened with the picture at the head of this blog post. I was minding my own business, shooting shadows at a corner in Chinatown one afternoon, when the two guys in the picture who were hanging out with some mates, came up to me and said “Hey, you gonna take our picture? Take our picture!”
So I did, almost falling over with surprise. Still chuckle every time I think about it.
charlene winfred 
I love talking to strangers on the street and making their photographs. I understand many photographers are shy about this but I find that if you see someone you would like to photograph on the street the easiest way to start a conversation is to find something about them to compliment them on. I still believe even in this disconnected digital age people still like to talk to other people if it is a passing conversation. As long as you are polite and respectful the majority of people I have talked to love having their photo made. So Charlene if I ever go back to Singapore and you run into to me on the street yes I would love to have you take my picture. (:
I’m glad to hear it, Pauly :)