I don't know if Letsrun is the best place to come for this but let's give it a try anyway. There is a guy in one of my classes (FYI I am female) who I've been talking to a lot lately (we've been sitting next to each other in class, etc.) and we've been studying together for our midterm this week. After studying today (with a few other people), we decided to go get some food at a nearby place. We got our items and as we were going to pay, he (somewhat casually though) asked if "I was okay with money." My immediate response was "Oh, yeah!" and I paid right after but I think I saw a flicker on this face when I said that now that I think about it.
I may be completely over analyzing this (what can I say, I'm an awkward distance runner too!), but does this possibly mean anything? My immediate reaction has always been to pay for my bills (not have someone pay for me), but there is also the fact that he offered... I prefer to pay for my own bills, but if a male offers to pay, is it polite to just say that I can pay? I have heard that some males are offended if you don't accept their offer to pay, but I feel like in this day and age this should be becoming less and less of a problem.