This photo is of a spectator during the 2007 Mosman Festival in Sydney. I posted it on Flickr and a friend on Flickr asked me how I was able to get close enough to get the shot, and how he wished he had the balls to do it. I thought you might like the story so here was my response.
I've realised it's got very little to do with the size of your "cohones" and more to do with the size of your smile. I actually have a photo of her from last year's festival where I didn't have the balls and took a sneaky candid shot. You can compare the two and see the difference.
Last year's shot
This year she was leaning on her fence like last year and watching the parade go by. Nobody was paying much attention to her so I went over and started talking to her. I think I said something like, gee you must have the best view of the parade, or something along those lines. She was just happy to have a chat and told me her whole life story. She's Mrs. Sales (if I understood her correctly), she's 96, was born a few blocks away in what's now the Fire House and she's lived her whole life in that area. After a few minutes I asked (with a smile) if I could take a photo of her and she said with surprise, "sure" as she quickly fluffed her hair a little to make herself look pretty. I didn't want her to think I went over to have a chat under the pretense of just taking her photo (which I really didn't, I actually wanted to find out more about her), so after the shots, I put the camera away and just had a chat with her for a few more minutes before wishing her a great day and walking away. I got my shot, she was happy to have had a chat for a while, and the photo is more interesting cause you now have her story to go along with it.
Of course, if you're at a public event like the APEC protest or walking along the parade taking shots of the people involved in the parade, just go up, with a smile, and shoot. I always find it nice to thank them as I'm walking off. If there's ever someone who didn't appreciate the photo being taken, depending on their size and ability to kick your ass, you either run like hell or remember this quote from someone I don't remember:
"It's easier to ask for forgiveness than for permission."
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Thanks for taking the time.