Yeah, mon. I bumped into Jetty at Alpha Fusion outside of B&H Photo on an evening walk during Photo Plus Expo. He had a bright white Konica-Minolta DSLR that caught my eye, I complimented him on it, and we got chatting. After a few minutes of talking, he was more than happy to let me take his portrait.
If you told me a few years back I would have walked up to a complete stranger in New York City, chatted with him and then taken his portrait, I might well have laughed out loud. But, it does indeed get easier with practice. And if it interests you at all, then you need to practice. Even when it isn’t important, or perhaps, more so when it isn’t important, practice. The worst case is someone says no! So what… there are millions more portraits just waiting out there.
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