That is a walking red flag, women have their flaws so do men, but you see a woman who loves to spend yet is not doing anything tangible to earn back what she spend can never be my choice either, if the man keeps trying to fill that hole, at some point, he would run out of funds and that is when the trouble will start, you said when he told her he doesn't have money to do what she want, she got angry, it wouldn't change when they got married... But like you said... You cant advice someone in love, he will learn the hard way by himself...