Comment by majormajor

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.