I have never had this problem you talk about. I go out and women buy me drinks, want to pick up food tabs, etc. and they have no intentions of 'friends'.
No one is talking about guys "needing help with money", the idea is that the scenario is framed as a "casual" and not some job interview where the guy displays that he can financially take care of the girl. Women are interested in the guy, not what he can provide for her materially. If a woman is truly interested in you and wants romance, she won't care how much money you have, whether you eat $5 burgers or a $35 steak.