My guy (we call him real Estate, or RE for short) made it very clear from the very first date that he was paying. And that he would always pay. He also opens doors for me, and other chivalrous things
As a very independent gal, this kind of freaked me out initially, because I was used to paying my own way... but then I realized, this is really nice. He WANTS to spoil me. He WANTS to spend his money on me. He WANTS to make me feel special and valued. I'd never had anyone do that for me before, and it was really refreshing. I do occasionally pay for things, like every once in a while I will pick up dinner and bring it to his place... or I get a Blue Apron box, but then I cook it and share it with him. Or if I want to go to something (a concert or event), and I invite him, I'm the one purchasing the tickets. It will never be 50/50 in terms of how much money we spend, he will always be spending more $$$ on me.
We have this joke, and we'll intentionally do this in front of other people because it's funny... the check will come, and he'll say something like, "Aren't you going to get that?" or something along those lines, and I'll respond, "No, that's not how this works." But the joke for us is there's a second part to my answer that goes unsaid. The full answer is, "No, that's not how this works. I have a *****, which means I don't have to pay."
This dynamic works for us, even though it took a while for me to become comfortable with it. Initially, it felt to me like RE might be trying to buy my affection (I am, after all, a decade younger than he is), and it took me some time to understand that wasn't the case, that my interpretation was MY hang-up and not necessarily a reflection of his intentions (my mother taught me that if anyone ever did anything nice for you, it was because they wanted something--in her mind, no one was every simply of generous nature). And initially, I also felt guilty of taking advantage of such generosity... but again, I realized that it was MY hang-up (again, thanks Mom). And I made him promise that he should tell me if he ever thought I was taking advantage.
Before my relationship with RE, I would have said that who pays should be 50/50... but now I'm changing my tune. And if I ever find myself in another relationship, I'll have similar expectations. Because it's not actually about the money.