Thats always a difficult thing to approach but from experience as it can be awkward and embarrassing for both parties.
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I think I gave real advice--a mediator. I also disagree with the rule of thumb that one should never lend money to family. I actually find pretty shocking the idea of withholding from family.
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I agree. Or something that doesn't require a face-to-face collection like email or voice message. If he/she takes time to reply then that when speaking would be best.