I've always thought the way my husband's family passes money around every month so no one faces financial consequences is odd, my mother raised us differently, like she would help if it was a dire situation but otherwise you're on your own. My siblings have never asked me for money and I've never asked them. My husband's family though, my mother in law is always giving money to her kids or letting them use her credit cards when they get in a bind and because of that they never face financial consequences like any other adult. They get money from her even if they overspent all their money on BS, when my mother would laugh if I asked and say "budget better next time". I'm not comfortable giving money to anyone, regardless if they have fucked me over in the past by not paying me back or something.