Other ideas: play Pokemon Go or try geocaching as a hobby. The main thing that gets you over that weirdness barrier is feeling like there’s a reason for you being where you are — like you belong there. The only way to get that is through exposure, but the easiest way to get THAT is to already have a reason to be there.

Geocaching will only work if there’s others doing it in your area, but it will also give you a sense of community and connection, which will help when going other places. Plus, both things are global, so you can take them with you anywhere.