So this is probably going to sound incredibly whiny, as it’s hard to write about this sort of stuff without coming off as an entitled brat. Please read charitably. 
I’ll set up a theoretical case to work with. Say you took your car in for repairs, and in the course of fixing the known problem your mechanic found a serious issue that needs to be dealt with ASAP, with an estimated additional cost of $1500. This is going to hurt pretty bad financially, but it’s not going to be disastrous.
At a family gathering, you mention the car situation but–having learned from past experience–you do not mention or even allude to the financial implications. Your wealthy uncle overhears and, having some idea of your money problems, immediately jumps in and volunteers to cover the unexpected $1500 fully. You decline, uncle insists, and in a moment of greed and weakness you accept his offer to help. (That charitable reading I asked for? This paragraph requires a ton of it. Please assume there was no fishing for charity or pity intended, and that the “you” of this story would have kept schtum if you’d known Rich Uncle Pennybags was listening in.)
Uncle writes a check for $1000 and says he’ll cover the rest after the work is done. Awfully nice of him, you’re pretty much in tears, and you try to ignore the voices whispering “this won’t end well” in your head.
The check clears, a month passes, and the repairs are completed for a total of $1507. Pretty good estimate! Your uncle has gotten really invested in following the repairs, and he asked you to call him as soon as you get the final total. So you do, and he says, “Ah, yeah. Little cash flow hiccup right now, heading out for my spring vacation and all, but I’ll get you in a couple of months. That OK?”
The little whispering voices are starting their “told you so” chorus, but you ignore them. You tell uncle he’s already done more than enough, you don’t expect anything else, he’s already gone above and beyond, etc. But he insists, and insists some more, and you acquiesce.
It should go without saying that you never get the $507 from your uncle, although you do get to spend Christmas hearing about the diamond studded beds he bought for his dogs. OK, that last bit is mean, but it’s a surprisingly slight exaggeration over the real situation. Let’s just say Unc likes making it clear he has money to burn, and all signs point to him having the cattle to back up his hat.
So after that long setup, the actual questions:
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How do you describe the situation between yourself and your uncle at this point? It’s completely wrong to say he owes you $507, but there seems to be some sort of unfulfilled commitment. On the other hand, these are the kinds of commitments–at least in my family–one doesn’t fully expect to be fulfilled when they’re entered into, so calling them “commitments” in the first place seems a little off. (Charitable reading time again: I’m not looking for an excuse to feel resentment here, although it’s easy to read it that way. It’s more that I’m genuinely uncertain about the status of promises of aid within a family, and what vocabulary can be used to describe them.)
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Assuming there is some sort of commitment, can you ever say, “Hey Unc, remember that $507 you said you were going to give me? What’s up with that?” Would it be acceptable–if crass!–to even mention it after, say, six months? Or is it something you let go immediately as soon as he postpones it the first time?
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What do you do when, inevitably, Unc starts lording his generosity over you? Some people seem to engage in giving only as an excuse to express resentment toward the recipients of their charity; assume your uncle is that kind of person, but also assume you knew that going in. What’s the best way to navigate between “You gave me a huge amount of money for no good reason, so you’re right that you are amazing and I kind of suck” and “You only gave me 2/3 of what you promised, which is kind of sucky”?
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Kind of a tie-in to 3: You really are grateful! And you express that gratitude both to Uncle and to the rest of your family. But, even though you don’t (or try not to) let it show, that gratitude is tempered a little bit by the $507. Which is maybe crazy, since if Unc had said “Here’s $1000 to help out” you’d think he was the greatest guy since the inventor of sliced bread, but as it actually played out…it sort of niggles. Is this an overly entitled feeling or is it acceptable to be annoyed that the reality fell short of the promise?
