Don’t worry about it, seriously. There is nothing awkward about being poor and it definitely is no reason to feel guilty, it just sucks. You’ve probably also experienced that people won’t necessarily help you out under these circumstances, even if you specifically ask for help and if you know they have the money. So, dignity is all you have going for you.
Also remember, there is wealth in other things as well besides money. Besides buying rounds when I could, I’ve always made a huge point out of volunteering and helping people in other ways. Throw your time, smarts and skills around like some people spend their money. Learn how to cook. Learn how to repair stuff. You’ll be fine.
True story: I have two best friends that I’ve known since kindergarten. When I was in a really difficult period a couple of months ago one of them said to me: “You know, if you really get in to trouble, I will always come and bail you out.” We’ve never had to try it out, but you can’t imagine the feeling of support that gave me. Now, I’ve just recently discovered that my other friend is actually insanely rich (compared to all the rest of us), he just never told us before. Guess who typically buys the rounds? Right, the first friend. Guess who is happier? Yup, still the first guy. But, I still love them both. Life is like that.
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.