Regardless of what you think, you're paying her. Either pay now or later, it's still you who would be doing the paying. If you manage to bag her, well, then you still have to pay for the house, the car, the bills, so might as well get started. But all is not lost, just hint to her what you like, and you might get a surprise, most of the time, if the lady is in fact a lady, she'll feel bad after a while and do something nice for you. If the lady is a byeatch, your sixth sense should pick it up and it's time to put on some army boots and kick tha byeatch to the curb. Despite all that, you, first and foremost, always have to be a gentlement. It's good for your rep, and that's the only way to be a jerk without retribution (THINK!). Don't dwell on lost causes and move on, and remember, playas are always gentlement.
If you ask, then you pay; even if you don't ask, offer to pay anyway, unless you're broke. If the lady is a sugar momma, then she's already expected to pay for you.