Cain doesn’t care, if he needs money, he gets it. If he can’t get money, he’ll shoplift. Ravenna doesn’t care either, because she’s very well off, but she’s not the type to buy useless things. She buys things she likes and wants. Winston saves his money, because on his own as a teen without a job, he has little unless he asks his mother. And trust me, he’d rather go homeless than to ask his mother.
Does your character have any toxic friends?