Yeah I've done some of that before. I found it a little harder with the 37mm since it meant I had to be much closer to the people. Some of the other shots towards the end of the roll I started to relax more, but I think with more practice I'll open up.
Also especially once there are some events in the city. Festivals of all sorts take place in summer and those are perfect for getting really close to people without anyone caring. I usually end up with some fun interactions with people during those, where they'll even just start talking.
RE: 35mm film street photography