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Street photography/portraits?

No.3291090 View ViewReplyOriginalReport
So here I was, having bought a D5300 and looking for new things to try out. Since I have been photographing landscapes for half my life now with various devices, I started thinking about trying out street photography and portraits.
Now, I am an awkward dude, but I hope to improve my social skills by approaching people on the streets and asking to take a photograph. Any advice for that, any dos/donts?
Another thing that has been ghosting around in my head is the need for a fast prime lens, around f/1.8. The only question is: 35mm or 50mm for portraits/streets?

Inb4 search catalogue for the exact same issue