When I moved overseas, she told me that I should do it, and I do on a regular basis - though not in the grocery store line, and I don't get anxious if I don't do it.
I've definitely made some interesting connections, including with a guy on a bus in 2012 who transferred me my first bitcoin on that bus and got me into crypto. I wish I knew he was so I could thank him.
I've never regretted reaching out to a single person. Sometimes people don't want to talk, and that is easily noticeable. Sometimes I don't end up wanting to talk to them, and that's a bit harder for me to exit.
Give it a shot, but do be conscious of other people's feelings and understand quickly if they want to be left alone.