Nabbeun, you are spot on. Now, that's an intelligent comment from a man who's been there.
As I've said, I've had a few of these relationships. I'd say half of them asked for cash for some dramatic reason. I don't usually give it, but once or twice I did because: a) it was a relatively small amount of money and b) I could afford to lose it.
I never got "paid back" either of those times, but I didn't expect to. No harm no foul.
A certain former girl who was once well known on this board once asked me for a loan of $10,000 to start up her own shop. I knew her well and I did trust her. I was sure she would have paid it back. No doubt. However, I didn't do it because I couldn't afford that amount. Period. We remain friends to this day (she's not in NY at present).
Basically, when the girls ask for money, they are telling you that you are just a preferred john, not a real, real relationship. Which is OK. It's part of the risk you run getting into it. But you have to know this or you will get burned. Once the question is asked, the girl goes from potential gf to something else, which is OK, because she's telling you that's what you are. As long as you know that, you can give or not as you see fit.
The other half never asked for anything and I never gave any. Good girls. I'm glad I knew them.