Why is it so awkward to lend a large amount of money to people who need it? Okay, I guess I know the answer, but still.....man.
Certainly, it's the kind of thing that people like us never do, usually can't do; in fact its effectively a deux ex machina arriving to solve an intractable problem, and we know how often those occur.
The impulse is to make the offer once, and, if rejected, to drop it. Well, we tried. Because, if they take it, what then? What do you do? Go on with life as if the offer was trivial? Ignoring it would feel as if the act is being taken for granted; talking about it would feel like you're required to be constantly thankful on the one side, or constantly wanting to be thanked, on the other. It would be the elephant in the room -- can't joke about it, can't make passing reference to it.You might want to know if things are still okay between you - are we cool? - but you can't without alluding to the elephant. Better to not even offer. After all, its not as if they expect it.
And yet - a good friend might have to change her life plans because of something that we can help to fix. Isn't it worth the awkwardness to try?