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Taking pictures of strangers, both with and without permission, is some of the hardest things I've done in my life. I have a lot of social anxiety, so it was definitely as far out of my comfort zone as I could get. I was able to do it for maybe a week. I had one lady get very upset and demanded I delete the picture. Another lady was verbally upset in passing. And of the people I asked for permission, maybe half declined. But I also had some ladies who were visibly happy to have their picture taken.
I thought I would get used to it the more I did it, but it really took a mental toll on me. I tapered out towards the end of that week and I haven't photographed strangers since then. I even made a blog thinking I would make it a regular thing... but guess it's not gonna work out.