For a while my local supermarket had a new manager and the check out girls would ask everyone, "so what have you been up to today?" and "what have you been doing this weekend?" and EVEN making specific comments on what you might be doing with the groceries you were buying. It was very hard not to say something utterly crass when asked direct questions about what I'd been doing that day.. oh I had some awful things on the tip of my tongue.
The process you describe T'Girl of getting to know people in shops etc.. best happens organically. It is actually stymied by there being a script the shop people have to run through in the guise of friendly customer service.