Who should pay for the first date? Who should pay for the second date? How often do you split the check? All questions in modern-day relationships. I've dated guys who have absolutely refused, under any all circumstances, to ever let me pay for a date. With one guy, the one and only time he let me pay was out of necessity, because we were at Taco Bell on a Friday afternoon and he'd forgotten his wallet. I know many straight guys who seem to take an issue with the girl paying, even if they've been dating for a while, and I think that's a flawed way of thinking. So guys, here's why you shouldn't be freaked out about letting your girlfriend pay once in a while.
The "provider" role really should go both ways
I know there's a cultural expectation, especially in more conservative circles, that the man is supposed to be the provider and "take care" of his female significant other. But that's a pretty impractical idea in the long run. Good relationships need a decent amount of give and take, and both partners need to be ready to be there for the other through hard times, financial and otherwise. Despite the cultural history on this issue, setting up one partner as the "caretaker" in the relationship, male or female, isn't the best idea. Relationships are a lot of work. That work needs to be shared between the two of you. It may seem like a small thing, but taking turns paying or splitting the check is one of the ways you can do that.
Even if you think you're just being polite, the reasoning behind it is still pretty sexist
Some guys are raised to believe that men pay for dates, and that that's just the way it is. That's what a "gentleman" is supposed to do. That's the way their parents taught them to treat a girl they're interested in. And that may seem all well and good, but think about why we teach people this. Is it just assumed that the girl has less money? Is it just assumed that she has a worse job than you, or doesn't have the resources to pay for you, or even if she does that she should be "letting you take care of her"? You can certainly pick up the check a decent amount of the time if that's truly what you want, but by letting her do the same you're letting her know you see her as an equal. Which brings us to...
No, it's not emasculating to let your girlfriend pay for the date
Because your masculinity shouldn't be contingent on how much money you make or how many meals you've bought her. Sure, she's your girlfriend and you want to do nice things for her, and that includes taking her out. But let her take you out now and again too. You're her boyfriend, after all, and she wants to do nice things for you. So let the payment thing be a two-way street. Relationship are, after all.