Lol... Well, in a situation where a guy has spent 2 hours telling me that women have only used him for money, I'm certainly not going to add to his grief!
Having him pay for MY dinner right after he's told me all about the times women have used him -- for free dinners -- would just be adding insult to injury. If anything, I want him to be able to look back and say, "Well, there was this one time when a woman paid for ME."
I completely understand about people being hurt -- we've all been hurt -- but the point where I draw a line is when someone seems to imply, "All these people have hurt me, and I know you'll probably be just like them." It's almost as if they're making a challenge that says, "PROVE to me that you're any different, and you're going to have to keep proving yourself." I'm happy to do that at the by covering the bill (I won't accept a date if I won't be able to pay for us both as a back-up, if need be.) But for me, that's also where it ends. If he is somehow requiring me to make up for someone else's wrongs by constantly having to "prove that I'm different", I'd rather move on.
It's a funny thing. I'll hear/read lots of opinions about how feminists and strong, independent women have ruined the Godly family unit, but for some people who say that, if you bring up something as simple as paying for her dinner and total mayhem breaks loose. It's almost a feeling of, "I just want someone to obey and submit to me -- but what do you mean, I'm supposed to pay for her dinner? Are you crazy???"
Even when I was young (junior high), I always had it in my head that I was going to make sure I kept a mental tally of what a guy spent on me and would somehow make up for that, because I didn't want guys accusing me of using them for money. There was this very sweet guy in junior high who used to bring me little gifts from the drugstore across the street, so one day I presented him with a t-shirt and Swatch watch (does anyone remember when those were THE thing?!) that I had saved up to get him. I was super excited to be able to pick something out and give it to him, and I could tell he was caught off guard, which I loved.
Anyway... Sorry for the long tangent. And I'm certainly not trying to say this can't go both ways. Guys, I know we women sometimes stereotype and lump everyone into the same boat and demand that you "prove something to us," and I am sincerely sorry for that.
Paying my own way, or offering to pay for for a guy is just my own personal way of trying to even things out.