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What are your thoughts on dating etiquette for women? Should women pay for dinner on the first date?

It’s been a great night of drinks, dinner, and conversation, but the evening is coming to a close as the bill is finally brought to the table. Questions start to flood your mind: Do I offer to pay? Did I do everything I could have to impress my date? Will there be a second date?

Dates can be stressful, especially first dates, but by following some dating etiquette, a woman can relax and enjoy the experience. Here are some guidelines to help you handle awkward situations involving the bill, and some other general dating advice for women.

How to Handle the Financial Aspect of Dating

Who should pay the bill when you go out on a date? What can you order on the date? It all depends on how long you’ve been dating, and how far you are into the relationship. The financial aspect of dating is much different for a first date, for example, than it is for a fourth or fifth date.

First Dates

Most men will pay for first dates, but some won’t pay or expect the woman to pay for her share. Here is some advice for a woman going on a first date:

Go Prepared. Even if the man asked you out by offering to pay for your dinner, bring enough money to pay. The man may forget his wallet, or be unable to fully cover the bill. Perhaps he intended to split the bill from the beginning. Or maybe the date just doesn’t go well, and he no longer wants to pay for your share. With so many possibilities, it’s a good idea to carry cash with you and be prepared to take care of the bill if necessary.
Be Considerate of What You Order. A first date is not the time to order the most expensive item on the menu, or to order multiple courses and pricey drinks. By the end of the date, you may quickly decide that the guy is not right for you. It would be inappropriate to let him know you are not interested, after he just spent half his paycheck on you.
Be Mindful of the Restaurant You Pick. If the man asks you to pick the restaurant, choose a moderately-priced restaurant or find restaurant discounts and coupons. Don’t select an expensive restaurant, and don’t ask to go to a fast food restaurant, either. You do not want the man to have to pay for an expensive dinner, and you do not want to insult him by selecting a cheap restaurant.
Subtly Offer to Pay. While most men will pay, it is important to make sure that the man knows you did not just go on the date for a free dinner. Some men will be insulted if you offer to pay, so you need to subtly hint that you are willing to pay. For instance, when the check comes to the table, reach for your purse. Chances are that the man will tell you not to worry about it as he reaches for his wallet. Just thank him, and let him know that you appreciate his gesture. If he doesn’t stop you, don’t be offended. Simply offer to split the bill, which is fair.

Subsequent Dates

Ladies, after you have been on your first date or two with a man, the rules change a little. Do not expect the man to continue to pay for nice dinners and evenings out, even though some men will still pay. Here is some advice as your dating relationship gets more serious:

Continue to Offer to Pay. You always want to arrive prepared, and if this is your second, third, or fourth date, the man may or may not allow you to pay, but at least you have shown that you are willing. It all depends on his belief system, how he was raised, and his current financial situation. If you find out that your personal belief system about how men and women should split the bills on dates doesn’t match with his, perhaps this is where the relationship ends.
Communicate. If you continue to date this gentleman, there may be a time when you feel it is right to discuss the financial aspect of dates. A conversation about how bills are split on dates helps both of you to understand what to expect. If this is going to be a lasting relationship, this may be the first of many difficult conversations about finances, and it is important to open the lines of communication from the very beginning.
Do What Works as a Couple. In this modern era of working women, there are a lot more options when it comes to paying for a date. Essentially, it’s about what works best for each individual couple. Perhaps you decide to take turns paying, or perhaps the man decides he always wants to pay. The key is to communicate about money, so that there are no hard feelings.

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A confession to the men I’ve dated: If I ever insisted on paying my half at the end of a first date when you offered to treat, it may have been because I never wanted to see you again.

My persistence to pay was—at best—code for, “Let’s just be friends.” At worst, “Beat it.”

We all carry assumptions surrounding that first date bill and how it ought to be settled. When those expectations aren’t met, the evening could end awkwardly. She might be offended if he doesn’t let her pay; he might be annoyed if she doesn’t at least offer to chip in.

It’s an early stage financial crossroads that could make or break chances for a second date.

So, when in doubt, how should men and women best handle that first date tab? And was I right to offer to split the bill if I didn’t like the guy?

I tapped relationship experts Marni Battista, founder of DatingWithDignity.com and Bernardo Mendez of Your Great Life TV for some guidelines.

Men: Offer to take the lead.

Battista and Mendez both agree that it’s generally best for men to pay on a first date. Yes, even still in 2014—a time in which, as I myself have written, women often outearn men.

But the fact of the matter is that men typically want to pay: In a poll last year conducted by LearnVest and T.D. Ameritrade, 55% of men said they thought the guy should take the check. As Mendez explains, many men feel fulfilled and accomplished when they see an opportunity to provide, even if it’s in simple ways like paying for a drink.

Perhaps more importantly, paying is a way for him to preen. “Even a guy who doesn’t make much money if he really likes you will try to impress you to the utmost that he can,” says Battista

As for women? “In my experience, 90% will be offended if a guy doesn’t offer to pay,” says Battista.

The data seems to support her claim, at least to some extent. That LearnVest poll found that 63% of women expect the guy to pay. And when researchers at Chapman University recently surveyed more than 17,000 people on the topic of first-date finances, they found that 39% of women who offered to pay said they secretly hoped the men would not let them. Meanwhile, 44% of women said they were annoyed when expected to help pay the bill.

So guys, pick up the check. It’s just a first date dance move that—more often than not—leaves each person happy and satisfied.

The exception: If she asks him out and picks the place, the experts say, she ought be prepared to settle the bill.