Should he pay?

Nothing wrong with it as long as you offer to pay for him now and then too. The whole thing about guys paying for girls comes from back when guys were the only ones with money to spend, so they had to pay for girls. Now that girls can make just as much as guys the reason behind that practice doesn't really apply anymore, and a some guys see that.

Take for example my situation: I went out on a date with a girl a few nights ago where I paid for her, and she says that she wants to pay for me next time around. I like that.

The best thing for you to do is to tell him how you feel about it. Tell him that it would make you feel like you were a better couple if he payed for you sometimes. He will understand, don't be afraid to tell partners things like this. My ex demanded that she pay for herself even after I offered to pay and then when we broke up she said she felt like she was "wearing the pants" too much. See what poor communication does to relationships, it ends them. Go talk to him about it and it should be fine. Good luck.

No, paying is not always the nice gentlemanly thing to do. Paying _was_ the nice gentlemanly thing to do until women stopped being ladies, and start being independent women. Now it's all up in the air: you can't expect guys to act like old-style gentlemen if you don't act like old-style ladies. It's a yin-yang thing.

Why is it humiliating when he asks for separate checks?

well honestly my last couple of relationships were like that but I didn't really care because I don't expect a guy to pay for me at all.. unless he asks me out for dinner than I expect him to at least pay... but I guess you can say that most men more than likely pay for a couple of dates...

I like what redhead said, about if you invite you pay, if he invites he pays... though for me, that's how I am with my friends, not my bf.

Im older (but not old...hah!) and I'm very old fashioned. Its been 2 years with my boyfriend and I still don't pay for any dates. My boyfriend said it best "Its my responsibility cause I'm the one courting you..not the other way around" There are times when we go out for drinks, he's talking with friends or I don't see him around so I go ahead and pay for our drinks when they are ready...he can't stand it when I do that and tells me to just start a tab or come get him. I still do it sometimes though... ;)

Ive always felt this way though, and tend to meet guys who feel the same way. Most of my friends on the other hand lean to paying dutch or taking turns paying, and tend to meet guys who want to do it that way. Personally, I don't mind paying (I hate dutch so Id rather take the whole tab) if I'm out with friends. If I did start paying for dates...Id either start seeing the guy as more of a friend than a romantic interest...or Id start feeling like the more dominant factor in the relationship. And I don't want that...so it wouldn't last.

Well, if it bugs you so much, slightly overestimate how much you spent on your meal, and pay for that part, he pays for the same thing for himself, and what's left over is the tip. It's kind of a courtesy, but not required in a relationship. Keep in mind that you haven't offered to pay for him, either. Granted, chivalry isn't dead, but trying to enforce it is a bad idea. Maybe if you both paid for each other, and alternated, it would be better. If he does and says all the right things, and is really sweet, then you should feel great that your boyfriend is so awesome, and him not paying for a meal is a minor thing.

sort of hint at how youd like him to pay for you sometimes
also instead of getting seperate checks you can just get one and then each pay half

I'd have a casual conversation about this. I don't always like the guy to pay so I've had that conversation before too. Just casually mention that you'd like him to pay for things sometimes. Tell him that it should be a mutual thing. He should pay sometimes, and you will pay sometimes. One-sided doesn't work.

Since he's made it clear that he doesn't want to pay for everything (by his actions), don't pressure him. To simplify things and avoid awkwardness, go half-and-half not with splitting the check, but with him paying for both of you half the dates and you doing the same.

A good rule of thumb for the first few dates, when you're NOT in a relationship yet is that the date-planner pays for both, whether it's the guy or the girl. That way, if you can't afford something fancy, you plan something within your budget, and if he wants to splurge, he's responsible. It's just simpler that way.

But since you're in a relationship, it's probably a good time to discuss this with your boyfriend. Just say that instead of always splitting you'd like to...(see paragraph 1). Even if he wants to continue splitting, at least you've made your opinion known, and since he's the great guy you say he is, he'll want to do everything he can to make you comfortable, so there's your answer!

Hope all goes well.