Dear Rosie & Sherry,

First of all, I would like to say that I love reading your advice on so many important subjects concerning single people today. Now I am in serious need of advice and I hope you can help.

I am a 28-year-old single woman living in New York and am utterly confused about modern dating etiquette. It seems that everyone has different unspoken rules, and they often clash with a big boom. I am particularly interested in the "transportation" issue during the first few dates. In New York City there are many men who do not own a car and therefore cannot drive me home after a date. What would be the norm under such circumstances?

I recently went out on a date with a successful lawyer and have a slightly disturbing feeling about some issues:

I was meeting him for a "quick drink" after work, which turned into a very enjoyable 4-hour conversation. He didn't want me to leave and I really liked talking to him so I was not in a rush myself. The problem is, I was planning to only meet him for a drink and did not eat dinner. But during the course of the long evening he did not ask once if I was hungry. I didn't want to bring it up for fear of being rude, so I returned home really famished.

The other issue is that after the date, during which I had two glasses of wine on an empty stomach and I am not used to drinking, he just dropped me off at the subway station. It was almost 10:30 p.m. and I have a 45-minute ride to my apartment.

One of my friends says that she would never go out again with a man who doesn't care enough to get her home safely, and that he should have paid for my cab. The other says it was a perfectly normal and acceptable behavior, since I am an adult woman who is capable of taking care of herself.

What is your opinion on all this?


Dear Sharon,

Sometimes, you can put a suit on a guy and give him a nice professional title, but it won't change the fact that he may be clueless about the right way to act on a date.

After it became obvious that the quick drink was stretching into a long evening, your date should have offered you a bite to eat. But let's face it, some guys don't think along those lines. It's possible that he wasn't hungry and it didn't occur to him that you were skipping dinner. Or the time could have gotten away from him. It's also possible that he was too cheap to pay for a meal.

We can understand your own reluctance to bring up the subject, but here's a suggestion in case you find yourself in a similar situation again. If your date asks you to stay past cocktail hour, you can say: "I'm enjoying myself and I'd like to stay longer, but it's dinner time and I planned to have something to eat about now. I don't want to turn your offer for drinks into something more if you're not up to it, but I'd like to get something small to eat if we're going to spend a couple more hours together."

As for the transportation issue: When it comes to ending a date, the different reactions of your friends proves what a gray area this can be. When a couple arranges to meet at a specific location for their first date, it is fair to assume that they will each get home on their own. In such circumstances, it's an added courtesy for a man to offer to escort his date to a taxi or subway, or even to her home.

Once you’ve passed that first date, however, we think that the person who invites the other out should take care of transportation arrangements (as well as their cost, but since anything goes nowadays this is something you two can discuss). Since that role usually falls on the man, we think it is fitting for him to either drive his date home or arrange safe transportation for her. Although a man may feel perfectly safe riding a subway at 10:30 p.m. in New York City, a woman probably feels differently.

Once again, the guy you were with could have been clueless. He probably thought it was a very nice gesture to take you to the subway. There is also a possibility that he could have been cheap.

Since you enjoyed this man's company, we think you should give him another chance. Too often, we have found that men with really great potential get passed over for second dates because they don't understand the finer points of dating. We notice that younger women have a certain amount of patience when it comes to dating a man who lacks dating etiquette. They'll attribute it to inexperience, or being somewhat inexperienced themselves, they will not get overly upset by it. We also notice that as a woman becomes more worldly, she expects her date to be more sophisticated.

It's true that by this time he should know to offer a date something to eat when "just for drinks" turns into an evening, or the gentlemanly way to escort a woman home. However, the fact that he hasn't absorbed this information doesn't mean he can't turn into a great husband.

Some of the male readers of our column may get upset at what we have to say next, but we can assure you that we're not out to bash guys. (Of course, there is a lot to say about how a number of women can improve in their dating skills.) If asked, most happily married women will admit that it took some work to help "socialize" their husbands. They may even describe, with good humor, how their future husband didn't know how to dress, choose a nice restaurant, escort them home, etc.

The reason they can look back with a smile is because they are quite happy with the man they married, and their husband has learned better social skills, usually through the woman's influence. In fact, in all good marriages, men and women learn a great deal from each other.

We're not suggesting that you change another person's basic nature, or that it is your duty to "fix" something that's broken. A man who is selfish or stingy will stay that way. However, a man who simply doesn't understand that at 8 p.m. the woman he is with may be hungry, is a lot different that the man who doesn't care if she's hungry and would do anything to avoid paying for dinner. Many guys are diamonds in the rough. They have good internal qualities and simply need someone to recognize that they will shine brilliantly after a little polishing.

If you decide to go out with this man again, try to concentrate on finding out about his inner qualities. At the same time, you can gradually let him understand some of your concerns about the earlier date, albeit in a non-accusatory way.

We suggest that you raise the subject of transportation now and drop the dinner issue for the time being. You can tell him that you appreciate his thoughtfulness in taking you to the subway, and that at the time you didn't want to spoil the evening by telling him that you are uncomfortable riding the subway alone late at night. However, you'd like him to understand how you feel so that you can arrive at a comfortable solution for both of you. Suggest that he help you hail a taxi, or accompany you home on the subway.

You'll probably find that in the future this man will be more sensitive to your concerns about travel. And if he's not, then you'll know that he's either too selfish to care, or his "coating" is too dense to penetrate.

Rosie & Sherry