We're getting into some philosophical areas here (and these are very deep waters for me, so forgive me if I misstep), but it sounds to me like you think the onl

We're getting into some philosophical areas here (and these are very deep waters for me, so forgive me if I misstep), but it sounds to me like you think the only way to get empathy is to put the other party to get into the same theoretical situation. I think there are other ways to get others to understand you and get empathy. I don't think you need to make someone else experience the unpleasantness to make them feel empathy, you can communicate unpleasantness without (in this case jokingly) threatening to inflict it. In this case the person you are talking to is probably not at all responsible for the original problem, so I think the need to consider both the human and the company you are talking to is larger than when dealing with a single person.