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I've heard women complain that they've had dates like this. That's too bad that it's come to this. I kind of go by this standard. I always offer to pay. If the woman doesn't want me to, I'll offer one more time, in a friendly manner. If they still say no, I'm not going to be pushy about it. It isn't a matter of pride or trying to get something from a girl, besides a date, and the chance at perhaps a relationship down the road. It's just good manners. People don't seem to be taught good manners and such niceties are lost on the masses.
I put that together with insecurity, for sure, but it took me a while to realize. I had an experience with someone who was violently insecure with his masculinity (often taking it out on me) and one of the things he used to berate me for was wanting to contribute to a night out. He wouldn't have it, so we stopped going out. Makes a lot of sense.
As for the regular phenomenon, I find a lot of men these days will pay for a first date (though I've heard stories...) but as they become more comfortable around you, this will stop. First they start complaining how expensive restaurants today are. Then they complain that what you want to do is too expensive. Soon they start asking you to meet them places instead of picking you up, and before you know it, you're paying the bar tab.
I have no issue with going Dutch treat, nor am I a golddigging party girl. It just appears to me that men today, even those with means, are more concerned with saving a dollar than taking out their girl.