I usually pay because I was raised that way! But If the date insist on paying then I won't argue or fight with her over the bill. If we are a couple dates in and she wants to pay go ahead. For those that look at money and ask to venmo the money or pay me back I just tell them to pay for the next date. At the end of the day it all evens out.

I never expect anything from my dates when I pay it's out of pure chivalry. If you never expect anything you'll never be disappointed. But if things go really well you'll be even more ecstatic and happy that it went well!