Having been both 'poor' and 'rich', here's some advice from experience: don't give your sister anything for her immediate needs not asked for. If she asks, th

Having been both 'poor' and 'rich', here's some advice from experience: don't give your sister anything for her immediate needs not asked for. If she asks, that's different. When someone is telling you to take money "because you need it",etc., it's hard to not feel like you are being judged as a screwup. Instead as a way to help, set up accounts for her children. Start putting money in a college fund (like a 529). Even in the strongest relationships people get weird about unsolicited money for the here and now, but helping to tackle a future problem won't have the same "superiority" effect. It doesn't feel like charity because it's not a immediate need, but more like a vote of confidence in your nephew/nieces - hard to explain why but at least that's been my experience. You also don't have to tell her about it right away. There won't be any question that you are doing it to boost your own ego rather than totally out of the kindness of your heart if you wait a couple years to let her know you've been saving for their future. It'll probably have the same caring impact on her as the $50 gift she gave to you affected you. Just my unsolicited advice :)