Great post. So many things you wrote are so correct about human interaction in a city. The point is that you are actually meeting the pharmacist. You're there

Great post. So many things you wrote are so correct about human interaction in a city. The point is that you are actually meeting the pharmacist. You're there every week. That's an opportunity. Say you wanted to talk to him more, I would not be trying to act like more of a customer by talking about medical conditions, I would be talking about things he might be interested in, or mention something else that I'm interested in, or something that anybody might be interested in (weather/current news/sporting event), or something related to the current situation. Or even just throw something out there - "you look like you might know about <certain thing>, my mom has one and was just asking me about it". Even if you're wrong they'll be interested in why you might think that about them which can move onto other subjects. "You remind me of <such-and-such person>". "Hey, you remind me of my dad, what's a good present to get someone like you?". Use your imagination and you can come up with a million of these. You could even just volunteer something about your life. "Nice day today, I'm in a good mood because I'm going on a trip away soon". If he's interested in talking he'll continue. Most people who are working boring jobs will want to chat with a customer that isn't annoying. I think it depends on what you want to happen in the end. Do you want to meet this pharmacist out as a friend or more, or do you just want more small talk? Small talk is, by definition, impersonal. If you want the relationship to be personal, you need to transition from small talk. Either find a common interest or show interest in his interests. TBH I find small talk pretty irritating and mostly enjoy being impersonal in the city. There's too many people to be friends with everyone, and I don't have time for many friends as it is. "How are you?" - "I'm good thanks"! Mostly when I do make the effort to chat, people are receptive.