Rules aren't meant to be broken

Anyone who ventures into the murky waters of modern dating should be equipped with a guide for the wary companion. There are more rules in the dating world than in any other sport I know. And to succeed in dating I firmly believe one has to have a sporting approach – go out there prepared, practice between dates, be aggressive but fair, and more than anything: know the rules, choose when to play by them, and more importantly, know when they should be broken.

There are some basic rules of chivalry that one cannot and should not take for granted. Dating in Israel made that blatantly clear to me, very early on in my courtship career. If I had to wait for my dates to open car doors for me, I would have spent more time waiting than dating. Even the obvious – such as having the door of the restaurant opened for you – is far from clear in the holy land. On one of my first dates ever in the country, I almost had my nose broken when I followed my date into a restaurant without considering that he would close the door behind him. It simply shut directly on my blower. I've taken precautions ever since.

And then there are the rules of engagement – whether to a do a post-date summary, announcing your desire to meet again, or your reason for not wanting to. This tends to be a woman's dilemma, as every man I've ever dated, regardless of what he was really feeling, said 'So we'll talk' at the end of the date. One has to wonder whether they even realize that they are saying that, or whether the phrase has become as natural as asking 'how are you' when you serve someone in a restaurant or shop, with no expectation of getting any kind of genuine response. So on occasion, the woman may choose to bite the bullet at the date's end and respond honestly. Examples include "I don't think we SHOULD talk", or "You know what? You're nice but not for me". Or my favorite let-down line of them all – "You may be Mister Right, but you're definitely not Mister Right NOW…".

Should this not happen, or even worse, should you actually WANT to see the guy again, the waiting game starts the minute the first date ends. There are so many rules here, and so many more exceptions to the rule, that it's all-but-impossible to know what to anticipate at this juncture. There are some schools that dictate a grace period of two days between the first date and the follow-up call. Sooner could be interpreted as clingy, desperate or plain obsessive. This is true except in situations where you're also truly interested, in which case he could call five minutes after the date ended and you'd be delighted. Of course, everyone who's ever dated also knows that if he doesn't phone back after three days, it's a lost cause and you should move on. Again, that rule can be bent if you're really interested, and any excuse under the sun would be considered reasonable when he makes a half-hearted plea for date two even weeks after you first meet.

For a few lucky people who are introduced to one another by mutual friends, there's the possibility of receiving post-date follow-up insight from the matchmaker. These rare situations may even elicit constructive criticism on dating technique or personal style, and they should be welcomed or even cherished. One of the funniest stories of post-date feedback was related to me this week by a friend who had gone on a mediocre date with a man who left her fairly apathetic. In fact, he seemed far more interested in his new cell phone and her job in the cellular industry than he was in her during the evening, and she had no expectation – or inclination – to hear from him again. So she was surprised when his number appeared on her ringing phone at the crack of dawn the following morning. A few seconds after she answered, she realized he had not intended to phone her at all, but for some reason his new cell phone was calling her number. She hung up, only to get repeated phone calls from him throughout the day. She stopped answering the calls, but her cell phone recorded his casual conversations until it ran out of space. She was shocked to find that for much of the time, she was the topic of his banter. She had a live recording of his play-by-play account of their date, heard a dissection of her personality and dating techniques, and to add salt to her wounds, had to hear him tell more than one fellow passenger in his car how obvious it was that she was more interested in him than he was in her (a clear case of mistaken date autopsy). While we all seek feedback in one form or another at one time or another, this recorded testimony of the bad date was just a little too much for my friend to take, and thankfully the ex-date soon learned to lock his keypad and the repeated calls stopped coming.

What does not offer much flexibility in Dating 101 is the issue of who pays. It's very clear, regardless of how liberated you are or the society you live in is. Men are burdened with payment obligations on date one, and they should take that into account when recommending a place to go. Personally, a drink or cup of coffee has always been my chosen form of blind date – making it a cheap date for whoever paid, and preventing long evenings waiting for a creepy partner to gnaw his way through his entrée before I could leg it out of the restaurant. Of course, any girl worth her salt would offer to pay half at the end of the date, and any man worth dating twice would refuse. At the most, the girl pays the tip while the guy foots the bill.

This ritual gives a lot of leeway for people who'd like to indicate their level of interest. For example, on a few occasions where I wanted it to be crystal clear to my date that I was not interested in a second date under any circumstances, I found myself insisting quite vociferously that I pay my share of the bill. It seemed to be the only fair thing, considering there was no chance of a return on investment for the poor guy across the way. Similarly, when I was interested in a second date, his refusal to take money for the bill gave me an opportunity to suggest that I'd pay next time, giving him a clear indicator that there'd better be a next time.

Which leaves us with the poor guys who, on occasion, leave their means for payment at home and are placed in that super-awkward position of having no money at all on their first date. A friend of mine told me recently that she had gone on one such date, where she ended up footing the entire bill because her date had no wallet with him. The fact that she never heard from him again didn't make her any more sympathetic to the guy. When discussing this at home, it was pointed out to me that this could be the ultimate dating test – pretend to leave all means of payment at home, resulting in a win-win situation. Either you have a bad date but it doesn't cost you a thing, or you have a good date and a great excuse to see her again under the guise of repaying the favor. And simultaneously your date's reaction to your 'tale of woe' will serve as a clear indicator of her generosity and understanding. In fact, the idea seemed so ingenious it made me wonder why it doesn't happen more often.

What is crystal clear to me is that these rules are ridiculous. There are too many to remember, they are restrictive and frustrating and make dating feel like one long complicated game without a referee or line judge. But what is even more clear is that when both of you are really interested in the relationship, none of the rules matter. Whether he calls you in a minute or a day, he pays or you pay, when it's right, it's right, and none of the regular rules of play come into the equation at all.