Yeah I feel similarly. I equate it once to when a coworker asked me to lend them $20 until payday. He didn't pay it back, I shrugged it off. I didn't think to ask anyone about it. Come to find out he had a gambling problem and he had asked others for money (some significant amount of money from people higher up the foodchain than me at my job) and he got sacked. Like lending money if asked by someone you know... if you can swing it.. so be it. The amount of weirdness and guilt coming from all this seems the odd bit to me. I do like the idea downthread of telling them to just donate the money when they want to to an org that helps people as paying it forward. But really all the weirdness this family is throwing at the LW down't make much sense unless they are a family that holds SECRETS and they like to use it as LEVERAGE and those are all red flags to me about how this family deals with problems.