Ask the Shadchan


I am a 23-year-old man. I work and also go to college, and I am getting ready for my first date. Of course, I am getting lots of advice from friends, brothers, and my Mom. Unfortunately, much of it is conflicting advice. For instance, I usually wear casual clothing. Do I have to wear a Shabbos suit on the date? Will the girl be insulted if I don’t? I would also like to know how long the date should be. I have heard everything from going out for coffee to a three- to four-hour marathon. What do we talk about for all that time? How personal should I get? People say, “Talk about your family.” Well, how deep do you go with a perfect stranger? How much does my date really want to hear? Do I open the car door before the date? Afterwards? Do I just drop her off or walk her to the door? I haven’t seen any men do these things once they’re married, so isn’t it a little artificial? Finally, a friend of mine’s wife set us up, so am I expected to go through her for a second date, or can I just ask the girl out again if I want to?


The Shadchan Answers:

You ask some very basic questions, and the answers depend on who you are and in what circles you travel. Never having met you, I can’t give definitive answers, but here are some general guidelines for a first date.

Regarding dress, the idea is to make a good first impression. If you were going to a job interview, would you dress in Shabbos clothes or “dress down” and risk giving the impression that you don’t give this first encounter the importance it deserves? The girl, I am sure, will be dressed and “made up” in the best possible way. She may look at you and think, “What am I getting into? This guy doesn’t value me,” and she will try to end the date as quickly as possible.

Of course, I don’t know what kind of “casual” you mean. I assume you do not mean a T-shirt and jeans, which are definitely not appropriate for a date in our circles. If you are talking about a colored button-down shirt and nice pants as an alternative to a white shirt and suit, this is very normal for working guys on a first date. Girls looking for a working guy might be put off by clothing that is too fancy. While I understand that young men who are planning to learn full time usually do wear suits on most dates, from your description of yourself as someone who works and goes to college, I would guess that this “business casual” type of dress would be perfectly fine. When you call to arrange the date, tell the young woman that you are dressing casually so that she will not be overdressed.

How long should the date be? No one can tell you that. You want to find out if you are compatible, so you need to discuss likes, dislikes, hobbies, education, the outside world and, last but not least, your family. You do not have to go into major family discussions on your first date – just a general outline. You will find a lot to discuss – from frum community happenings to the recent presidential election, even her favorite team, if she is a sports fan. I would suggest going to a place where you can sit and talk but also see some “action,” which would give you an opportunity to find a topic of interest to discuss.

Believe me, if the date goes well and you feel comfortable with each other, you will have plenty to speak about. Going out “just for coffee” can turn into a marathon if you have mutual interests. By the way, you do not have to – nor should you – do all the talking. You need to be a good listener and show the young lady that you value her opinion. In short, a date is what you and the girl make of it – it is not measured by a particular length of time.

You did not mention picking up your date, but you should definitely pick her up at her home. If she is a local girl, her parents will want to meet and speak with you – so there, again, be prepared, because the first impression counts. Upon your return, you should walk her to the house door, if for nothing else but safety. Your comment that men don’t do that after they are married is only a shame on them. This is mentschlichkeit and concern for the other person.

If you are interested in the girl, do not immediately ask her out for another date. She may need time to think about it, and it is not advisable to put her on the spot. Speak to the shadchan and let her find out if she is interested in going out again. I generally advise that if the first two dates go well, by the third time, you can ask her personally if she wants to continue seeing you.

Let me make one more suggestion to help ease your anxiety. In our circles, unfortunately, many young men have never spoken to a young woman outside of their family, which causes a lot of awkwardness on a date. I recommend that you ask a cousin or sister with experience to go out with you on a practice date, so that you will be more comfortable when you finally meet your date. I know someone who did this, and his date turned out beautifully.

Aside from the mechanics of dating, you should be prepared in other ways. I hope you have a clear idea of what you are looking for in a wife and will not ask everyone for their opinion. Rather, find a trusted mentor whose hashkafic approaches you admire and whom you would like to follow as you begin to think about building your own home. (Ultimately, though, you must make the final decision – no one else.) This mentor can help you navigate not only dating etiquette (such as whether or not you should open the car door) but also more substantive issues that might come up.

If your mother advises you, realize that she is likely telling you what was done in bygone years. You should consider that she may not be wrong, even though her advice doesn’t live up to the “formula” that our community has artificially created and imposes upon everyone. (You do this on date one, this on date two, this on date three…and so it goes.) You should value your mother’s opinion even though you may not agree with her.

I hope I have given you some insight as you begin the dating process. May everything work out well for you, iy”H, and may you find your zivug in the very near future. Much hatzlacha!

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