Dear Rosie & Sherry,

I, like so many others, am in the dating phase of life. Unfortunately, I have never made it past a second date. With most of the guys I went out with, the feelings were mutual. Sometimes, however, they aren't, and I'm beginning to worry if I can actually make it past a second date.

Your advice column(s) have helped me immensely. Now I'm hoping that you can provide some "second date topics," because right now, I find I am playing it by ear, or just following his lead, which has thus far gotten me nowhere.


Dear Jill,

We understand how frustrating and worrisome it can be to date a succession of partners and never get past the second date. The fact that this seems to happen to a lot of people doesn't make it any less painful. There are ways to turn this around, and recognizing an unproductive dating pattern, as you have, is the first step.

We've identified six major reasons why daters have trouble getting past date number two. We don't know much about your specific dating history, as far as identifying which of these issues, or combination of them, is causing you difficulty right now. Nevertheless, here's an overview of the most common pitfalls that keep people from progressing with their dates:

(1) Dating someone who's not in the ballpark.

Do you realize very quickly that many of the people you go out with are totally wrong for you "on paper"? That's a reason many dates don't work out. You can minimize the possibility of this happening by doing some "homework."

We suggest asking some basic biographical information (age, where born and raised, education, family background, height and build), what he's now doing in terms of education and career, his basic life outlook (in terms of religion, lifestyle, etc.), and where he sees his life going over the next 5 years. Find out if he's got some of the personal qualities you believe are very important and ask what he's looking for as well. You may want the names of a reference who can fill in some details and verify that he seems to be a moral and emotionally stable person.

It's not a good idea to say "yes" to someone who sounds like a nice person and wait until the date to learn some of these details. Why should two people invest the time and emotional energy into planning and going on a date, only to learn in a matter of minutes that they're not what each other is looking for? The starting point for every "dating suggestion" you accept should be that each of you seems to have the basics that the other seeks. If they aren't present, don't agree to go out in the hope that maybe your personalities will jell and then your differences won't matter. Those differences are usually too significant to be worked out.

If you're more selective about the suggestions you accept, you may have fewer dates. However, dating for marriage isn't a numbers game. You're looking for the right man, and if a date doesn't turn out to be "the one" but is close to what you're looking for, you can be encouraged by the thought that the right person is probably close by.

(2) Personalities that are totally wrong for each other.

The first few dates should be an opportunity for two people to get an initial sense that their personalities may be compatible. Usually, this is something even the most expert matchmakers can't predict. Sometimes, a couple who seems to be perfect "on paper" realizes from the start that the match is very wrong. They can strongly dislike each other's personalities, or become physically and emotionally exhausted trying to maintain a conversation. One of the daters can say or do something that offends or insults the other. Or, one party can be very uncomfortable with the other's appearance.

While people can often sense on the first or second date that they're not compatible, it may take several dates before they get a sense that they are compatible. It usually takes time to reveal the many facets of their personalities and start to become comfortable in each other's presence. That's why even people who have a so-so time on their first date should agree to go out a second time, and if the second date is better, to be open to the idea of a third date.

(3) Unrealistic expectations for the first two dates.

If you come to a first date with expectations that are too high, you set yourself up for disappointment. It's a mistake to go on a first date thinking, "I'll just know if it's right for me." It often takes two or three or even four dates for two people to realize that they are beginning to relate to each other, starting to like each other, and are becoming physically attracted to each other. Think of a first date as an opportunity to break the ice, and the second date as part of a process of getting to know a little about each other.

One expectation that virtually insures that things won't move beyond the first or second date is the thought, "Maybe this is the person I'm going to marry." This is an automatic turn-off. At this stage you are not yet accustomed to your date's looks, mannerisms, and personality. If you start to imagine being married to him, you'll actually stop being receptive to the idea of getting to know him better.

(4) Conversational difficulties.

Some people are challenged by the mechanics of dating. It may be a good idea to match a person who is shy or who needs some time before she is comfortable enough to converse easily, with someone who is patient and know it may take a while for her to open up. Someone who is very nervous about dating or has trouble maintaining the flow of a conversation can role-play dates with a friend or a mentor, in order to feel more comfortable and build conversational skills and confidence.

Often, people who consider themselves good conversationalists have difficulty figuring out what to talk about and how much information to reveal during the early stages of dating. It's a good rule of thumb to spend the first date on topics that can be called "airplane talk." These are the subjects you might talk about with your seatmate on a long airplane flight -- interesting information about yourself and your background that is not too personal and that doesn't reveal strong emotions.

Here's some topics that allow you to convey something about yourself without revealing deeply personal information:

  • Playing "Jewish geography"
  • describing what it was like to grow up in your hometown
  • discussing why you chose your school/yeshiva/profession and what you like about it now
  • talking about your favorite hobby and why it appeals to you
  • comparing your impressions of a city or country you've each visited
  • discussing an interesting article you've read and your reaction to it

Someone who's comfortable carrying on a conversation may lose track of the fact that a date is an opportunity to learn about the other person. He may unwittingly monopolize the conversation and give the impression that he is only interested in telling about himself, instead of engaging in a dialogue and asking questions that convey genuine interest in learning something about her.

Another common difficulty for people who are skilled conversationalists is spending too much time discussing a particular topic (such as the intricate details of one's job or office politics), or focusing too much of the conversation on intellectual topics. It's important to show a date your softer side -- your tastes, what you do for fun, what you appreciate about your life and the people in it, for example. When dating partners convey a mutual wish to know each other better, and are able to observe different facets about each other that pique their interest, they're more likely to consider going out again.

(5) Raising the anxiety level.

Some perfectly lovely people unwittingly scare their date away. A man may feel so comfortable talking to his date that he begins to reveal details about his life that make her feel uneasy and wonder why he would bare his soul to a virtual stranger. Anyone who over-does compliments or praise to a new dating partner usually comes on too strong too early. It's okay to say, "I had a great time tonight, but may be over-the-top to gush, "You're such an amazing person. I like you so much." Your date may not know how to handle the fact that you're more "into" the relationship at this early stage. And a man will be turned off by the overtures of a woman who asks, "When will we see each other again" or "Will you call me?" after the second date.

(6) Unrealized ambivalence to dating.

One reason why getting past the second date may be difficult for some people is that they have ambivalence to dating and don't realize it. Part of them wants to meet the right person and develop a relationship that leads to marriage, and part of them is terrified. They may come from a difficult background and be worried about having to eventually reveal a "secret" about themselves. They may have seen their friends or family members struggle with troubled marriages or divorce and wonder what lies in store for them. Or, they may wonder if they are ready for marriage, perhaps thinking that they want to learn more about themselves, or accomplish a particular goal before "settling down."

Whatever the reason for this ambivalence, unless you can acknowledge these mixed feelings and resolve them (sometimes with the help of a third party such as a mentor or a therapist), you may unwittingly turn down the idea of another date with a partner who has potential, or do something to sabotage the chances of being asked out again.

As you can see, getting to "date number three" isn't just a matter of finding some good topics of conversation. We hope that this discussion has given you some insight into what may have been holding you back in the past and what, if any, changes you can make to date more productively in the future.

Rosie & Sherry