money matters

Mr Ng and I were on the phone today when he related one of his friend's money woes. The said friend, a student, had been incurring a lot of dating related expenses and while not experiencing a liquidity crunch yet, is starting to wonder how he could control his spending a little. On the other hand, he is used to paying for his girlfriend whenever they go out and he doesn't know how and when he should broach the subject of money.
Later in the evening, a friend told me about another friend whose bf had just lost his job. Since she is a student, he had been paying the bulk of their living expenses. Now that his income stream has been involuntarily cut off, she will have to find ways to deal with that and to a certain extent (in my mind), is obligated to help him out and to contribute to their joint expenses. How would she be able to help out and justify it to her parents who are financing her studies? Would it be appropriate to ask mum and dad for she and honey's living expenses?
Money is a very sensitive topic, and dating can become an expensive endeavor. What is the correct approach you should take? A male friend who is adamant about going dutch all the time with his gfs, as he believes its not the girl's right to demand otherwise and that if they like him for who he is and not what he can offer, they will accept it happily. From what he told me, his gfs have all been receptive of this arrangement from the get-go. Other friends like to pay for their gfs whenever they go out because it is just an extension of their appreciation and love towards the other party. And this method works too. So who can judge what's right and what's wrong? There might be a happy medium somewhere, but its pretty elusive for what I can tell.
4 years into dating the same guy and I still haven't gotten it. And while I think we have a pretty balanced approach towards managing money (undoubtedly helped by my laissez faire attitude towards gifts), there are still times I wish he could be even more generous. Pay for all my meals, won't you, darling? Other times I would be frustrated because I have to reciprocate those meals by buying more gifts and other opportunities to buy him lunch because I don't want him to feel underappreciated for his efforts and to think of me as a financial parasite. And I expect this dilemma to continue, unless i suddenly am bequeathed with a trust fund and pak and i can live happily ever after without any worries because my great great great grand uncle thrice removed gave me a billion dollars to swim in =)
But for the boys and girls out there who are not recipients of generous relatives, little miss fiscally prudent here will like to remind you, In the end, money won't buy ya love... so do whatever you want, just dont go broke!