Do you think you should pay most of the time or you dislike it when you're the one paying most of/all the time?
Would you prefer she paid most of the time or you think both partners should take turns?
Is there any difference if you're at the early stages of dating/relationship ?
By traditional gender roles, the man is supposed to be the provider and the woman is supposed to be barefoot, pregnant, at home, actually making the house. I was taught this as I grew up, in a rather closed-minded environment.
Later in my life, when I left the social setting of my youth and ventured into university, I exposed myself to more influences that got me thinking along different lines: gender equality. The topic is heard about relentlessly in the adult world, whether it's through mainstream media, initiatives at one's employer, or the subject of academic research.
Two very different views of women offer two sets of answers to your questions. If a woman is seen as financially dependent, the man should assume his traditional role of provider, whether dating or in a more serious relationship. If the woman is seen as financially independent, the man expects a "tit for tat" arrangement, where he pays and then she pays (wash, rinse, repeat). Unfortunately, our society has double standards when it comes to men and women being equals, and in many places (including the realm of relationships), women get special treatment. This is very much a societal norm, hence some men expecting "tit for tat" arrangements will still pay for their dates at some point (i.e. beyond a first or second date). I was among these men, just like a lot of other guys.
Looking at this another way, guys who view dating as an economic transaction will find paying acceptable, as along as the benefits of paying across dates outweigh the costs. If a guy wants casual sex, he'll buy a gal some coffees and a few meals without a hitch, as long as that furthers his cause with enough (though not necessarily all) women he dates.