The biggest trick is to find someone who would like to have a conversation (most people would rather not). The most important sign here is eye contact and wheth

The biggest trick is to find someone who would like to have a conversation (most people would rather not). The most important sign here is eye contact and whether they're actively observing their surroundings as opposed to reading a book, talking with friends, staring into nothing. Then you have a good chance if you use an icebreaker, e.g. talk about things they have on them. (A monosyllable answer and avoiding body language means they do not want to talk, find someone else.) Some people won't shut up at all, especially older ones. If you want to hear interesting things you might have to steer the conversation a little, so eg you can hear about how the city used to be in the past as opposed to how their doctor's visit this morning went. However, the most important part is to find the ones that want to talk and broadcast the same intent. (There is better luck when it's not just people going to/from work, those usually want to be left alone.)