Depends on what the conversation is about. The ring on my finger? (similar to the example above?) No-no.
The weather, because it is summer and hot? Ok. Just banter.
The crowded store and the fact that I had to stand in line 5 minutes? ("Crazy, we didn't expect that many customers today!") Yes! Shows they are aware and care.
It's not that I don't want to interact, I just don't want to be dragged into that 'we're friends' game.
In my experience it feels different in part because you have the person in front of you (it's harder to fake seeming genuine face to face).
It also feels different because they are talking while they are doing something else, unlike on a phone call where these questions are preventing you from doing the communication you need to do to finish the call. It would be more similar to Trader Joe's employee stopping you on your way in to ask you a bunch of questions about your day and the weather outside.
I live in NYC and was actually thinking about Trader Joe's and checkout lines here generally when I wrote my comment. Cashiers here generally don't waste anytime with small-talk and that's understood as common practice since we're all in a hurry. In other parts of the country, some small talk is expected and one party will be viewed as rude if they don't participate. I prefer we skip it.
