Most of the time I follow this standard approach: first, I ask her expectations, financially and not only. Very few would reply with an actual number, usually they would ask back for an offer. Then I'd say that I prefer to start with a per meeting allowance, until some trust is established between the two of us and that in my previous Sd/Sb relationship the agreement was for $250/meeting (maybe 300 if she's very good looking).
Many ladies will reply asking for 300 (or 350). Some ask for more, but I never go higher than that.
Next step is to meet for drinks, and if everything goes well the second date ends in a hotel room or apartment.
Never, never pay her for dinner or having drinks. But do pay the bill, of course.