Paying shouldn't just be a ploy to test how your date is going to react, obviously. But still, how they respond gives you some insight into their personality. If they're pushy about paying after you've insisted, that's important to know. If they're so into you picking up the tab that they rack up more money on it, that's also valuable info to have.
Personally, being an independent woman, i don't mind to pay ;) why shouldn't I?
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What's hotter than a woman showing that she's into you by smashing society's rules and making it clear she's not there (tonight at least) for the money?
Just by saying that, I could fall for you so fast, Natured!
Of course, the rabbithole goes much deeper. If a girl would date a homeless man (one with charm of course), then things become Very interesting! And that is the ultimate statement of an independent woman - in demonstration of status and financial independence, and intellectual freedom from social constructs.2