I totally agree with you--I just find that a different enough thing from simple role reversal that I wouldn't call it that.
Your example about money is one that comes up a lot for me. I've been a student for only a few weeks, but I've been unemployed and broke for more than a year, and do my best to avoid awkwardness about it--I'll accept someone covering me but try to make sure they don't feel obliged to. I do worry about it happening too often, though, because while I certainly would repay the favor given the means, I'm not going to have the means in the forseeable future.
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I think it's important that zigdon only talked about things he would ask of other people in his comment, and you only talked about things you would do for other people in yours. I think that's the source of the difference. In particular, you're talking about going out of your way for other people who did not necessarily ask you to, which is a pretty different kettle of worms from making and accepting requests. He's not describing what he's willing to do for his friends; he's describing how big a request he's comfortable making of his friends. Choices about which requests to accept and when to be altruistic without prompting (which is what your examples sound like) use different heuristics.
(I'm comfortable speaking for zigdon a little bit because I know him fairly well, but I'll nudge him to fill those in himself if he cares to.)
Good point. It took me some time to rethink the relevant strategy.
OK, so a workable strategy might actually be a slight variation on the proposed system. Let's head back for a second: why do we sometimes feel uncomfortable requesting something?
I was thinking about this and I believe it might come down to our dread for getting a "no". In a sense, when people respond positively, there seems to be no problem with the appropriateness: it was appropriate to ask*. It is only when you get a reluctant "maybe..." or a "no" that things get really uncomfortable.
This changes the problem into a matter of being able to predict the outcome of the request. In other words, being able to predict the answers that people are going to give. If you can be fairly certain you'll get a yes, it is most likely appropriate to ask. This skill will invariably require empathy and (yes!) a "simulation of an external mental state" (aka "flip the roles").
*: Mind you , you'll also have to mix in moral considerations, because some people are easy to take advantage of this way. (When people are "unable to say no".) Luckily that is a pretty rare situation.