Haven't had that problem yet °-°
Well, I'm not an active RPer anyway, but when I see some people in the Inns, I just casually walk up and insert myself into their conversations (while asking in /tell if that is alright, ofc).
I don't even HAVE a backstory or anything, I just make that stuff up while I go along xD

I think it's easy to have too much nervousness and expectations tied to it when you overthink stuff beforehand