Money can be so divisive in close relationships. We sometimes see it as a symbol: of independence, providing, status. And just as money itself symbolises those things, giving it to other people can also trail symbolism: resentment, taking advantage, obligation.
One way to approach this is to ask: What's fair? You could litigate that forever. Of course, you might well be in the right: it might be the fair thing, or at minimum the kind thing, for him to help you out. But what's fair and what's kind are only worth so much if the person in front of you doesn't agree. Do you want to have to persuade him? Do you want to be extracting compliance with norms that, to you, are obvious?
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