That's lame. He never pays for you? Fail.
Call me old-fashioned. I think the guy should pay more often, at least in the beginning of the relationship. If at some point a couple agrees to go Dutch on everything, that's fair, but you aren't even going Dutch if you sometimes pick up the full tab and he never (?) does.
"He has a lot of bills." No kidding. Who doesn't?! If he's that strapped, maybe he shouldn't be dating. Or he should at least save up for his dates like I did in high school and college so I didn't have to mooch off my dates. He could also have you over to his new house and cook for you if money is that tight. There are ways to be generous that have nothing to do with money. Have a little dignity, man.
As dating offenses go, being a cheapskate isn't the worst thing, but it's not okay if it bothers you. It bothers me not just that he's cheap, but that he doesn't seem the least bit interested in finding other ways to keep you from paying so much if he's really that tight.
Should you be worried? No, you should just stop paying all the time. If he can't pull his weight, he needs to stay home and eat ramen alone.
Thanks for the question.