@sociallyawkward,
I think he's a jerk.
But there is also, currently, zero incentive for him to change. After all, he gets to have sex or near-sex (making out) with you and he doesn't have to spend a dime on you. You're not in it for the money, I assume, but when someone can't even be bothered (and with prompting, no less) to spend a hundred bucks on an occasional decent night out, then you have to wonder what else they don't want to give you, and what else they can't be bothered to do.
You don't say whether he's dirt poor, or constantly working, etc. That would change my answer, but not much. Consider this - my father really
was dirt poor when he was dating my mother. He used to take her to the airport and they'd watch the planes take off and land. Or they would go to a restaurant and he would have the cheapest thing on the menu while allowing her to have whatever she wanted (after maybe a month of dating, she realized what he was doing, and ordered cheaper food, too, or would just have coffee and claim to not be hungry in order to save him a little money).
The bottom line is that even an economic argument doesn't hold water.
But the other half of the equation is that
you aren't insisting on anything. So insist! It does not have to be expensive and it does not have to be couched in terms of a threat. And there's also nothing that says
you can't make the plans. So if it bothers you, make plans and take control of this situation. If he whines and complains and hates it every time, and essentially sabotages your good time, you might want to think about what that passive-aggressively means, and whether you want to continue putting up with it.