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Dating Advice #157 - ABCs of Dating

May 9, 2009 | by Rosie Einhorn, L.C.S.W. and Sherry Zimmerman, J.D., M.Sc.

Basic guidelines for getting the dating ball rolling.

Dear Rosie & Sherry,

I really feel I have no clue how to get this dating process moving. I am focused on dating for marriage, and I usually get to date 3 or 4, and then the girl breaks up with me. I've made it way past that one time, but it was so obvious the girl liked me I didn't have to even work at it at all.

Now I feel clueless about how to proceed in a courtship. I don't know how long dates should last, how to end a date that is going well, what kind of questions are good to ask on a date, who should take the lead in talking, what to do about telephone calls in between dates, and how to develop a courtship that seems to have promise.

Should we discuss our plans for the upcoming year and near future? If it doesn't come up in conversation, is it good to bring it up anyway? When and how is it appropriate to give a girl compliments? How does one know when to end a date -- it's sometimes hard to know if she is having a good time or if she wants to leave. Do women in general want a guy who will take charge? Some of these questions are really silly, but I would like some input, as I really value your opinion.


Dear Dick,

Your questions are by no means silly. We find that a large percentage of people who are dating for marriage don't have a good idea about how to develop a promising courtship. Years of working with singles have led us to the conclusion that contemporary singles should try to adapt old-fashioned courtship practices to their own lifestyle. The idea behind these "practices" is that it takes time for two people who think they have common values and goals to develop an emotional connection with each other, as well as the other ingredients that can form the foundation for a good marriage. It may take a focused couple as little as a few weeks to arrive at the realization that they are right for each other, while others may need several months.

We recommend that the first date be considered an ice-breaker. Meet for coffee or dessert, and plan on seeing each other for no more than two or two-and-a-half hours. You can even tell your date in advance that this is the time frame you feel a first date should follow. This gives the two of you a chance to feel more comfortable in each other's presence, minimizes awkward silences, and gives you something to build on for your second date. We also suggest that you go into the first date with no expectations other than you will be meeting a nice person with whom you have some things in common. Concentrate on simply meeting someone new and learning a little bit about her -- don't think of her looks, her mannerisms, or whether you think she'll make a good wife.

Steer away from deeply personal subjects, until you're more comfortable with each other.

If you find first-date conversation awkward, think in advance about the topics you can discuss and how you can develop them. Steer away from deeply personal subjects -- in other words, topics that can lead to a discussion about painful or embarrassing information, or deep feelings that should be reserved for when two people are more comfortable with each other.

Instead, talk about what it was like growing up in your hometown, what you like about the neighborhood in which you live, whether or not you've ever been to Israel and describe your experiences, or a hobby that interests you a great deal (including how you first became interested, what you have created or spent your time doing in connection with the hobby, your feelings when you work on a project).

Don't spend more than 10 minutes discussing your job, and don't go into long, boring details about the intricacies of your job description. Instead, why not explain why you chose the field you did, what you like and dislike about it, and some of your best or worst job-related experiences.

Remember that these conversations are two-way streets. Don't monopolize the discussion. If you realize that you are doing too much of the talking, stop, apologize for doing so, and ask your date some questions. It may be that you have to "lead" the conversation because the woman you are with is a little on the shy side. After you've described your own hobby, if she doesn't volunteer her own information, why not ask her what she most likes to do in her spare time, when she first became interested in her hobby, if she has produced or worked on any projects she really enjoyed or is proud of, etc. Don't be afraid to allow the conversation to get off on a small tangent.

All of the questions we have suggested will help each of you learn a little bit of the other person's history and how he or she feels and thinks. If you don't have a strongly negative reaction to your date, we recommend that you ask her out again, for a slightly longer second date. Try not to stretch the date beyond 3 hours (4 hours only if you are engaged in some kind of activity that prevents you from talking, such as a concert. Actually, we recommend waiting until at least the third date for this kind of activity, since the first two dates are better spent getting to know a little about each other). Save the longer dates for when you know each other a little better, and will feel less awkward with the periods of silence that every couple experiences.

If you plan on asking for a second date, do so within two days of the first date.

If you have a good time on a date, tell this to your partner. Or, you can say, "I enjoyed meeting you." Don't promise to call back if you have no intention of asking her out again (once again, we recommend asking her for a second date unless you had a very unpleasant experience, or realize that the two of you are definitely moving in different directions). Women should use the same guidelines to accept a request for a second date. If you plan on asking for a second date, do so within two days of the first date. If a man waits too much longer, a woman starts to doubt that he'll ever call, and as a defense mechanism against being hurt will start to lose interest. Even if the two of you are well-suited to each other, if you wait too long it will be difficult for the woman to regain the lost enthusiasm and want to go out with you again.

It takes many people two, three, or even four dates to realize there is something that they would like to explore further. That's why we cannot give you a hard and fast rule as to how and when to decide whether to keep going out or to stop seeing each other. It may take a few dates for you to realize that you enjoy spending time together, want to learn more, and are starting to develop a chemistry.

Sometimes, people keep dating because they realize the person they are seeing has many fine qualities, and really would like something to come of their courtship, even though they are troubled by something they view as a significant problem. (A few examples -- she doesn't seem to share your value system, his insecurity really bothers you, after five dates you still don't feel any physical attraction, you sense that she is too dependent on her mother's advice and approval.) They continue to go out, hoping that the problem will work itself out. In our experience, this doesn't happen. A courtship that leads to marriage often has small bumps in the road, but not major ones, especially ones that crop up very early in the dating process.

Here are some other topics of conversation that the two of you can explore as you continue to go out: your respective tastes in food, clothing, furniture, artwork and music. The differences and similarities in the way you were each raised. People whom you admire the most. Your favorite vacation. The way you would best like to spend a "free" afternoon. Your most treasured possession.

As you learn more about each other, introduce some more philosophical discussions -- your attitudes about honesty, for example, or a moving spiritual experience, something that made you decide to become more connected to Judaism and God, the importance of giving charity, etc.

If you would like to compliment her -- on an idea she has, the way she expresses herself, her appearance, an item of clothing she is wearing -- you can certainly do so, but be sincere. False compliments and undeserved superlatives are a turn-off.

By the fourth date, we recommend that the two of you engage in some interactive activities so that you see each other in different settings. Go fishing, take a tour of the botanical gardens, go paddle-boating or bowling, paint ceramics together, pack food packages for the needy, ask her to help you buy a birthday present for your mother, find a historical site you are both interested in seeing. Why not have each of you pack one half a picnic lunch, and go on a hike?

As you feel yourselves making an emotional connection, pick up on things your date says to show that you hear her and would like to make her happy. If she says she likes a certain kind of candy bar, why not buy her one? Buy her the newest CD from her favorite group. If she likes a certain flower, buy her one beautiful specimen.

Don't wait until you are both tired or the conversation starts to drag to end a date.

If you find that you really enjoy a date's company, feel that you are becoming more connected, and look forward to seeing her more and more, don't make the mistake of "overdoing" it. It is a good idea to have one or two long dates, in part to see how each of you reacts when you are tired and your guard is down, but limit the rest of your dates to 3 or 4 hours. Don't wait until you are both tired or the conversation starts to drag to end a date. You can say something like, "I'm enjoying myself, but I'd like to save some of this conversation for the next time we see each other. Why don't we go now, and talk about when we can see each other again?" Or: "I enjoy talking to you, but I don't want to stay out too late tonight. Can we call it an evening?"

Try to go on no more than two dates a week, although you can speak a few times during the week on the telephone, although we recommend against hours-long conversations. Give yourselves something to look for when you see each other face-to-face. Now that you are beginning to build a history together, you can talk about interesting or funny experiences at work or school, a news item that piqued your interest, or something you saw that reminded you of her. Eventually, and depending how focused the two of you are on engagement and marriage, you'll also discuss how you picture Judaism in your own home, the emphasis you feel each partner should place on Torah learning, community involvement, the kind of material lifestyle you would like to have, and how you would like to raise your children. As you become more comfortable with each other, other topics will flow from these.

Don't worry about whether the woman you are dating wants a "take-charge man." Be yourself, but display some self-confidence. If you are a little unsure of yourself, prepare for your dates by in advance by practicing conversation. Other ways to prepare for you date include selecting in advance where you will go (or two choices of locations you can present to your date), cleaning and gassing up the car, having enough cash or credit cards on hand so that you don't need to run to an ATM, etc.

Beyond this point, as questions arise, particularly when it comes time to think about becoming engaged, you may need a trusted, happily married person to act as your sounding board. We recommend that you find a married friend, preferably someone who has been married happily for a few years, to act as your dating mentor to answer the kinds of questions that will arise.

We hope this has been helpful, and wish you the best of success,

Rosie & Sherry


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