I’ve spent years of therapy trying to overcome my fear of talking to strangers. Mostly it just feels inappropriate and unwanted; like I would be intruding on people. I can talk to strangers when there’s an appropriate social context (e.g. clerks / service people). But lacking the right context, it feels deeply uncomfortable. Has anyone overcome this problem? Where would you go to interact with strangers–importantly w…
First: Work a job that is socially embedded. Restaurants, grocery stores, front desk retail, anything customer service related. Getting comfortable with people has a weird out-of-order solution where if your discomfort is visible, the interaction will sour; find something that forces a fix to the initial discomfort, like the jobs above. They'll act as a shim that'll let you bypass the initial anxiety.
Second: The emotions you wear on your face are what perpetuates a conversation. If you can find a reason--not act, not fake--to want to talk to someone, to learn about them, they will immediately, unconsciously pick up on it, and return that excitement. Conversely, if you don't trust someone, or think they don't want to talk to you, they wont want to talk to you, and they won't find you trustworthy, either. It's a counterinruitive, ready-fire-aim thing. You don't need to be perfect at this, you just need to be aware of it. People are excellent at vetting intentions.
Third: The idea that there's somewhere you can go that will make socialization easy is a farce. Interaction is "permitted" everywhere, and you can try it anywhere. Go for several short conversations instead of putting all your effort into one. You should be fishing for enthusiasm: if you get no effort back, then it is unwanted. Drop it and try again with someone else.