Dating Etiquette: When to Whip Out Your Wallet

Money and the "Dollar Diva" are often at odds because as much as women like to exercise their independence and free will, a surprising amount of women (including me at times) are bound by old fashion ideas when it comes to men and money.


First let's address the concept of a "cheap" date. Is there really a valid argument for considering a man to be a cheap date because he doesn't pay for the meal, entertainment, drinks or whatever costs were involved with the date?

Is it really fair to consider a man who does not pay for a date "cheap" when under the same circumstances that label would not be placed on a woman? Much can be revealed about how truly "modern" you are by how you answer these questions.

I call this the "Dollar Diva Dilemma" because it represents the classic double standard when it comes to money. If the same rule would not apply to you as a woman then it should not hold true for a man.

Deep rooted beliefs die hard and even in the 21st century a large majority of women still believe that how much a man spends on her (or doesn't spend) is a direct connection to his feelings about her or at the very least, an unwelcome introduction to his "cheapness."

Generally, a man who prefers that a woman "pay her share" will feel uncomfortable bringing it up because he's afraid that the woman will consider him to be cheap. That might not necessarily be a true or fair assessment of the person or the situation.

On the other hand, a large majority of men feel uncomfortable with a woman paying the bill. They see it as insulting and believe that it somehow suggests they are not capable of providing.

The whole thing can be pretty confusing for all involved, so what's a Dollar Diva to do when dating? Here are a few ideas.


Ladies, if you ask someone to dinner, I believe that you should be prepared to pay the bill. When the bill comes to the table, make an effort to pay it. However, if he insists on paying the bill, let him. The next time that you go out, (assuming there will be a next time) make it known that you will be picking up the check.

If he asks you out to dinner, you should still make the offer to pay and be prepared for him to take you up on that offer. This is not as much of a matter of pride as it is a matter of principle. If you have no intention (or means) of paying at least half the bill then you should not accept the date. Period.

Being a Dollar Diva often means wearing your independence as a badge of honor. If that's the case, then act like it. You should always have the financial resources available in that pricy Prada wallet of yours to get yourself out of any jam that might be created if a date goes wrong. That includes cash for a cab or car service to get you back home safely, money to cover the meal, movie or anything else that you decide to do, and access to a cell phone or calling card in case of emergency.

The truth is one man may be offended if you offer to pay the bill or even just your half while the next man would be delighted and encourage you to have at it. Neither is better than the other, but to avoid feeling blindsided, open communication up front is the key. Never just assume that the man will pay.


When the bill is placed on the table in equal distance between you, who should reach for the bill first?

The old fashion answer is, the man should reach for it first and that gesture will signal that he is taking full responsibility to pay.

The modern answer is, the women should leave the check in place but reach for her purse. This generally signals her intention to pay (at least a portion of the bill.) If reaching for your purse does not cause the man to make a move for the check, then the woman should assume the full responsibility to pay.

Don't get flustered or annoyed for being "stuck" with the bill, especially if all date long you're telling him how independent you are, and how annoying it is that men are intimidated by strong independent women.

However, if the man is willing to pay the bill, as the woman who has also enjoyed at least half of whatever was shared, you should at least make the genuine offer to split it.

Or, if you believe that paying the bill will cause an uncomfortable moment at the table that you absolutely want to avoid; you can always discreetly leave the table (i.e. go to the rest room) and provide the server with your credit card in advance. If you do this, you are assuming full responsibility for the bill.


The restaurant industry is a very demanding business, when eating out you should expect to get great service from your waiter or waitress and you should be fully prepared to tip them accordingly. I suggest at least 20 percent of the bill.

If your date insists on paying for the full bill then it would be a thoughtful gesture to offer to cover the tip. Be sure that you have cash on hand for this as it will be awkward to try to put it on a credit or debit card.

Have various loose bills available that will allow you to leave the tip without asking for change and always round up to make the tip an even dollar amount.

Sanyika Calloway Boyce knows all too well that "winging it" is a terrible way to mange your money and your life.

Financially frustrated and facing bankruptcy in her 20s, she was determined not to be a victim. Now in her 30s, she is the CEO of her 10-year old company, an International Speaker, Top Selling Author of several books on personal finance.

Sanyika is a sought-after authority on money matters and is often quoted by and interviewed on shows such as: The Today Show (NBC), The Morning Show with Mike & Juliet (FOX), In the Loop with iVillage (NBC), Money Matters Today with Mary Caraccioli (CN8) as well as numerous other shows. Visit her online at

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