As with so much else: if you don't know, ask. And know what you want, and say so.
If you want a rough equality, say so.
If you're uncomfortable paying for everything, say so.
If you're uncomfortable having your dinner paid for, say so.
Something that comes up often in dating is that one person has much more expensive tastes than the other -- or just a different set of circumstances. Last summer, for instance, I took my bf along on a vacation I'd planned. I'd paid for the house rental and told him he'd just need to take care of his own transportation and food. I knew he was unemployed, but also knew he had some money and help, and besides he'd have to eat anyway, and transit wasn't going to be much. What I'd forgotten was that the seaside town was actually quite an expensive one with no large cheap supermarket, which is fine with me because I don't eat much -- I could pop down to the little overpriced market, pick up some bread/cheese/fruit and call it a day. But he's a very high-metabolism guy, and eats tons, including a lot of expensive veg, so his groceries were actually substantial money. (Had he wanted to, he could've taken a bus and done some shopping a few towns away, but he didn't.) So that caused some problems. Solution: if we were to go back there, we'd have to plan for his groceries.
I will also, depending on who it is, let rich people pay for me. I'll almost never let a single dad pay for my date, because wtf, spend that money on the kids.
The main thing is talking. It doesn't have to be right at the outset, first date, but you can bring it up nicely in a non-blamey, non-aggressive, non-I've-been-victimised-so-often-in-the-past kind of way. You can talk about what kind of entertainments and meals you like, what your budget is. And what it may come down to is that if one of you wants to do pricey things and the other doesn't or can't, and the fancy person wants to do fancy things together, s/he may just have to pay for both. If you like each other, some compromise is reasonable there.
One thing I really won't accommodate, though, is "I need to pay for you because otherwise it emasculates me." I'm not responsible for a man's sense of his own masculinity, and it's a road I won't even start down. You figure out how to be a man by your own bad self.