At the beginning of the project I was shy too but after talking about it with them and doing it constantly steeped out of my comfort zone and now it is more comfortable.

Thing is that as photographer it is something more "normal" and I dont look as a creepy/harasser man , and some of them get really really happy to get profession photos for free so I think it is a win/win scenario.

I do get nervous at the beginning but once I do the first one I start to relax and I just keep going,

Something that also push me to do this is that i depend on creating content to earn my living so when I go out to make these photos/videos I really can't return home without doing at least 1 or 2 of these