Dear Diva Rebecca,

I have been single for a few years and enjoyed most of the time to myself. But now I am ready to hit the dating scene once again. I know times have changed, but I still do not know how much. My biggest question arises when the check for dinner arrives. Who pays and when? Chivalry or women’s lib?

Sincerely,

Which Wallet,
Greenwich, Connecticut

Dear Which Wallet,

Times have indeed changed and the answer is no longer that simple. There is no cut and dry answer anymore, except in a few obvious scenarios.

If you have been shamelessly flirting with a cute new lady and finally have the nerve to ask her out and she accepts, you pay. Whoever asks the person out for the first time should pay, even if you are a woman asking a guy out. It is common courtesy. If you are seriously courting this lady, you should offer to pay for the dinner and the date the first three times, at least. This is chivalry and it is very romantic. This is also where women get confused too….should she offer to pay? Yes, you should, and on more than one occasion. But if the man insists on paying, let him. Otherwise, you could end up hurting his ego if you turn him down and pay your way. On that note, for the guys who are reading, if a woman insists on paying, it really is okay to let her. It doesn't mean you are less of a man.

If your female date does offer to pay, this is a good insight into her personality. It shows she is generous, she does not expect too much, she isn’t a dinner whore and she is actually independent. Still, turn her down and pay the bill. That is, of course, if this is actually a date.

One reason why a woman might opt to pay is because she doesn’t want to feel obligated. Some women feel that if they let the man pay for dinner, it means she will have to reciprocate sexually. So first, you’ll want to establish if this is actually a date. Are you having lunch at an all-you-can-eat buffet or are you having a romantic candlelit dinner at a French bistro? If you think this is actually a date, it is still more appropriate to insist on paying. But if you get the feeling that she only opted to go out with you on a friends-only basis, let her pay if she insists. And what about the 'feeling obligated sexually' part? If you have concern there, you can easily make your date feel comfortable by letting her know that this will be an early night for you because of early morning obligations. And try not to be too touchy-feely if this is a woman you barely know.

There is one major problem facing men who are deep in the trenches of the dating front line. And that is the DINNER WHORE. Back in 2006 the New York Post broke the story on the proliferation of dinner whores, thereby coining the term. It has become such a widely accepted concept that Urban Dictionary has inducted the term into its catalog of contemporary terms and phrases. Basically, a dinner whore is a woman who accepts lavish and expensive dinner dates without ever entertaining the notion of having any sort of physical or intimate relationship with the man. Her company alone should be enough and is considered payment for the Dom Pèrignon, escargot, a four pound Maine lobster and crème brulee. Where a high-priced escort is a sophisticated version of a hooker, a dinner whore is the sophisticated version of a "mooch", with no sex strings attached.

Many dinner whores are obvious. They are amazingly beautiful and way out of your league. Some even openly advertise themselves on Craig’s list! Unfortunately, most dinner whores do not wear signs. But you can recognize a few subtle hints:

• As I said before, someone who is so gorgeous and sexy that she would naturally be considered way out of your league.
• When the bill comes she asks you, "Are you going to expense that?"
• She brings along a couple of glam friends, without asking, and expects you to pay for it all.
• She doesn’t seem remotely interested in anything you have to say.
• She instinctively orders the most expensive bottle of wine on the menu before you can even make a suggestion.
• After six dates, she still has not offered to pay one dime and you have never even been close to first base.
• Before she accepts the date, she asks, "Where?" first, as if her acceptance is contingent upon the dining arrangements. A dinner whore will only let herself be wined and dined at the best and most exclusive places.