I think your boyfriend is a freeloading douchebag.
If this were a case of two grown adults alternating who pays for dinner, that's one thing. Most relationships I've been in have either done this or gone dutch most of the time, at her request. It's not; he's just mooching.
Start making him pay; paying back at least half of what he owes is a good start. And if he won't pay up, dump him. Believe me, with moochers, it only gets worse from here.
The way I was raised back in the early 80's the guy should pay for the meal. However in today's society the woman gets butt hurt if they don't get to pay on occasion, so it's always good to alternate.
I actually dislike "the guy should always pay for the meal", myself, not the least of which is the fact that it's a very princessy attitude for a woman to have. I do think a guy should cover the first and maybe the second meals, but if we're getting to the third meal, dutch, for Pete's sake.
This ties into a very common sense piece of advice, which is never date somebody who doesn't have a job.
I don't even consider someone if they don't have a *good* job. Or in the process of getting a good job. Like in college and working a shit job just to have something to feed yourself with.
I was once asked out by a guy who works the night shift at Target. 27 years old, living in his parents basement. I asked if he was in school. Nope. He also had a two year old son.
I turned him down. No way will I even go there. It's not that he had a kid. Lots of us do, myself included. But he was doing zero to better himself. I cannot and will not handle that. No. Just no. Dan is right. Never even consider someone who doesn't have a job or their job is a shit job (and they are older) and they aren't even in school. Believe me, it's just not worth it.
Well, I think a gentleman always pays for the first date, or at least offers in the case of women who aren't into old-fashioned ways. Beyond that, either you make sure to do things evenly or whoever plans the date pays. Otherwise, it gets to be really messy and people get resentful.
"I think your boyfriend is a freeloading douchebag."
^ Bingo.