There are a couple of general indicators determining which of these three options is taking place. Once you've learned them, you'll be prepared to handle any tricky dating scenario. Take a look and sort out your confusion.
WHEN SHOULD THE MAN PAY
On first dates: First impressions are important. On first dates, it will be the best bet if the man makes the first move when the bill comes. This goes not just for the very first date, but throughout the early stages of the relationship. Paying for things is not just the gentlemanly thing to do, it also indicates that you are responsible, steady and well-established. The girl will be impressed.
If you asked her out: A good general rule when it comes to these situations is to ask yourself, "Who asked who out?" If it was the guy who instigated the date, then he will be expected to pay. In fact, it's good for the man to be prepared to pay, regardless of whether the girl asked him out or not because girls always like it if the guy foots the bill.
On special occasions: For special events, such as an anniversary, birthday, holiday dinners, the man should offer to pay. It makes them appear gracious and classy. Guys should remember not to make a big show of their generosity by letting the girl know how much a meal cost.
WHEN SHOULD THE WOMAN PAY
If she asked you out: Once again, the guy should be ready to pay even if she asked him out. However, in this situation, it's more likely that she will cover both of you, and why not? The date was her idea. Unfortunately, some men still have a problem with letting women pay, but there is no reason to feel insecure if this happens occasionally.
On your birthday: Obviously, this is the one occasion when she should cover her date and he should accept gifts or treats on his special day. She should be more than happy to pay.
If she's adamant about it: If, for whatever reason, she absolutely insists on paying, the simple solution is to just let her. Weigh the cost of angering her versus the slight embarrassment of her whipping out her plastic for both of you in a fancy restaurant.
If you're a steady couple: Once you've reached the stage where you're splitting all your bills, you've likely fallen into the steady couple category. At this stage, there is no longer any reason why only the guy should pay for everything, especially if both of you have similar incomes.
On joint purchases: If you're living together or going on a vacation, split all the bills for items or services that you'll both be using. If you're travelling a long distance in her car, pay half the gas money. The opposite situation, if she doesn't immediately offer, there is nothing wrong with suggesting that she should contribute. You can't go wrong if you remember to let her take the lead, and respond accordingly, or be prepared to pay the whole bill.
So enjoy yourselves without worrying about expenses.