I usually end up paying for the first few dates, as it seems to be custom/chivalrous.
However, I kind of wish this were inverted. I much rather pay for a woman I like than one I don't have any interest in going on a second date with, yet first dates are when I'm the most likely to end up paying--it seems when it's most expected of the man to pay.
And I could see that making sense when dating in a traditional way because you'd already know the person. But as it stands, with my well-documented use of dating apps, it's like we exchange five messages, and then I'm supposed to treat them to a night out.
Some women have even tried to insist I take them out for dinner and the whole thing. I always refuse. It's not that I wouldn't be open to doing that for someone I really like--of course, I have planned dates and covered the costs happily for women I've been seeing--but it's like I have no idea who they are at that point, and I'm not going to be taking out everyone I meet online for $150-200 outings. That'd be a major expense.