Boss man wants me to have more conversations with the customer that's more than just "hi", "will this be eveything", and "have a nice day". What should I do?
You could maybe add a generic "how ya doing" and they'll say "fine," but like >>16789582 said, I really don't want to go much further than that at the checkout counter of a fucking gas station
Or if you really want your boss to stop, take the conversations too far.
>how many kids do you have
>how was your childhood
>how much money do you make
>do you have a good relationship with your father
You're not out of line, then. Most people want to get their shit and get out, and even if they want to converse they need to fuck off if it's busy because the guy behind them wants to get his shit and get out.
If it's slow, then you could maybe small-talk BRIEFLY about the weather or something neutral like that, but frankly anyone who goes to the gas station and expects to chat lengthily with the employees can fuck right off, for they are the scum of society and should not be catered to. In other words, when you have a Chatty Cathy, just grunt noncommittally until they give up and leave. Don't be outright rude, just don't play their sad, empty game.