dealt with a range of situations like this before.
a.) girl accepts the nice gesture, is very thankful, awesome. makes you feel good
b.) girl insists you split it, ok no problem, great.
c.) girl frequently asks you if you want to go out for drinks or dinner, never offers to help out, you start to wonder if you're being taken advantage of.
Over the summer I was dating a girl who was still in college, so I knew she was essentially a broke college student and that's fine. So of course I paid for dinner for us and drinks but this girl would ask me to hang out and go out for drinks multiple times a week. I basically don't drink, but I really really liked her a lot so I went along with it for a little while but time and time again she would run up the bill ordering expensive drinks, and then expect me to pay for it over and over again.
Maybe I'm crazy, but it started to annoy me. Paying $100+ a week to go out and basically let her have drinks on me very quickly started to feel like she was taking advantage even though we hung out plenty aside from that and were hooking up and all that jazz. Idk...I think it should be a 2 way street. I'm all for being a gentleman as much as possible. but as somebody else said, it gets to the point where you have to limit your dates because you can't really afford to burn money like that.