Can I pay?

It's not a wrong move, but different guys can react differently. If he was raised to be a provider, he might feel ashamed to let you pay, and he might feel weird when you suggest it. All you can do is suggest it and see how he reacts.

Actual dinner, and you'd pay? You need to come into my life, haha.

I wouldn't be offended at all, in fact I'd encourage it to be like I'll pay for one day, you'll pay the next, etc.

But there are those arrogant guys (no offense to anyone) that insist on paying. To avoid awkward inferiority, try talking to him about it first. After all, each guy is different.

I pay for most of my dates with my girlfriend because I have a lot of money and she's just scraping by, but I do not consider it an insult for her to want to pay for something. If anything it indicates she likes me enough to want to spend money on me, so that's a positive thing.

But every guy is different, for all I know he might freak out about it. This might be a question that you know the answer to best.

He might take it as an insult if he is an old fashioned type of guy thinking oh big old macho man has to pay, but women want equal rights and some maybe not you demand to be paid for so its mixed signals and kinda messed up, I myself would be ok if I was with a girl and couldn't afford something at least she would be understanding enough to know I was going through some sort of hardship, plus going dutch never hurt anyone.

No, that's not the wrong move! Before I got into real estate, I didn't have too much money, and I spent a lot of my money on my fitness and diet. I like to go out with girls, so without money what I would do is just get them to pay for me :D
Even now, I don't usually pay for stuff if she wants to pay.

Also, what type of guy is he? Some guys feel bad when a woman is doing what a man's supposed to do. Perhaps the next time, you can suggest him a good place for a date, then you pay for it, see what he says. Just get along with wtv he says and ignore it, he wouldn't do something ridiculous like break up with you or kill himself. You can have the upper hand if you play your cards right, too.

Well, the only thing I would worry about is hurting his feelings, but that really depends on your guy's personality. Some guys might feel inferior if their girlfriend pays for dates/things they can't afford, but others are totally cool with it. If you want to go through with it, maybe try something along the lines of, "You've taken me out a bunch of times, now it's my turn! " It may be a good idea to let him know up front that you plan to pay, so he doesn't worry about how he's going to pay for the date. Best of luck!

It's great that you want to help pitch in, but if he's like a lot of guys, he pays because he thinks it's his job to pay. If you try to pay for something out of the blue, he may feel like you're taking away his "masculinity" (you know how guys get weird about stuff like that! ). My suggestion would be to do it for some sort of occasion. Even if you have to make it up. "I know I've been busy this week and haven't made much time for us. Let me make it up to you - I'll buy us dinner. " or "You were awesome at that basketball game/band concert/ballet recital. Dinner's on me tonight. " This way, you can squeeze in a few fancier dates, show your appreciation more, and still let him THINK he wears the pants. Everybody wins!