I agree that expanding communication with strangers is important. But starting with "Do you mind if I sit here? Or did you want to be alone with your thoughts?" and then continuing a conversation for 10+ minutes is a real struggle for me. Sometimes I even wonder—how exactly does this kind of individual conversation actually help me? Maybe this is just me.
Yeah it'll be hard. But with a lot of practice it'll get easier. I think part of the practice is recognizing "they don't want me to continue this conversation" and bailing, vs trying to force every interaction to be a deeper conversation.
I never practiced "idle conversation with a complete stranger" like that because I was lazy. But I did practice making normal, non-sexual, conversation with women on dating sites and dates so that I could go from "isolated in school, then after going online, low response rate and never more than 1 or 2 dates" to someone in a long-term relationship. And recognizing that sort of "ok there's just not any interest here, move along" signal was definitely relevant there too.
Skills take investment.
My parents didn't give me nearly as many opportunities to practice these skills as they had when they grew up, and pop culture actively encouraged me not to talk to strangers as a kid, so I had to work harder at them as an adult. But it was worth it.
Is it a matter of skill, or a matter of courage?
>how exactly does this kind of individual conversation actually help me?
It doesn't. It just helps the speaker.
That makes me think—why do I enjoy conversations with friends then? What's really the difference between a friend and a stranger? Friends annoy me too, maybe even more often than strangers do.