YUTOPIA’s Guide To Jewish Dating

For a prelude, first see the last post. For now, let’s get right to it.
Jewish dating stinks.

Everyone has their reasons and explanations. I’ve heard people blame the men, the women, the shadchanim, the Rabbis, and the whole culture at large. Of course, none of these discussions are productive. Even assuming one could find fault with any element of society, it’s unlikely that change will happen on an institutional level. More importantly, it doesn’t help the singles with their current situation.

As a friend and Rabbi, I’ve spoken to many people about their struggles in the Jewish dating world. As a single myself, I’ve personally experienced my share of disappointments and frustrations. I am not a professional therapist, nor am I trained in psychology. I’m hardly an expert in relationships, and I don’t have the greatest track record. However, I do think I have a decent understanding of the situation and of the many people affected. I also have a tendency to think too much.

I’ve started putting together my thoughts on dating and I’ve tried to offer some practical advice for singles. Unlike many comments I’ve seen and heard, I’m going to focus on what you, the individual, can do. Men, women, shadchanim, and rabbis are all out of your control. If you’re having trouble finding someone, no one can simply create a person for you.1 If you’ve fallen for someone, you can’t control if that person will respond favorably. However, you are in control of yourself, and only you are responsible for yourself.

My thoughts on dating are constantly evolving, and therefore are subject to change.

The Problem
Part of EndTheMadness’s theory is that people look to characteristics as opposed to the totality of a person. This is true to some extent, but it only solves part of the problem. From what I’ve seen, people have these incorrect attitudes of dating because they do not articulate what it is they are looking for. Even talking about “what someone is looking for” is a misleading statement as it typically invites responses from characteristics. The problem in the Jewish dating world is more fundamental than people realize. It expresses itself not only in the pettiness of checklists, but in the insensitivity of shadchanim. Simply put, we’ve forgotten what really makes a marriage work.

Paradigm Shift
Like many people, I had my answers to the “what are you looking for” question, based on what I thought I wanted. Alternatively, other people had their ideas of for what I ought to be looking. More often than not, this resulted in dates which looked good on paper, but just didn’t translate well in person. This experience usually left me (and sometimes a shadchan) extremely frustrated. Here I am having difficulty in dating, I find someone who seemingly meets whatever criteria I have, and it still doesn’t develop beyond a date or two. This was be extremely demoralizing not only for the disappointment in the result, but it also made me question my assessment of myself as an individual.

Recently, I decided to take the reverse approach. Instead of beginning with characteristics I think are attractive, I decided to look at the people to whom I have been attracted. Meaning, over the years I have dated, I have liked some people more than others (to varying degrees of course). Regardless of what people may have thought, there was something about these women that attracted me to them. What did these women have in common that I liked them more than anyone else?

Although this is a logical question, it’s not always helpful. When I looked at similarities in characteristics, I’ve found that many of these women were very different people. Some were more genteel, others outgoing, some were dry intellectuals, and others were hippies (for lack of a better term). In fact, some people told me that they would never have thought of setting me up with my ex at all, and yet we maintained a positive relationship for a time. Not finding any common ground in personalities, I was still left with the question, what made these people so special.

What I realized was that what attracted me to these people wasn’t that they were “smart,” “nice,” or whatever, but for whatever reasons I felt that I could have a relationship with these women. Of course, the nature of the relationship would vary from woman to woman, but the point is that I felt that I could have both an intellectual and emotional relationship of some kind. What mattered wasn’t that there was an identity of ideas, beliefs, or feelings, but there was a compatibility which cannot be articulated.
Dating isn’t even about the gestalt of another person, but of the relationship between two people.

YUTOPIA’s Alternative

What is truly amazing is how something so obvious gets overlooked by so many people. We’ve forgotten the simple truths of relationships to the point where we cannot even articulate our feelings. We’re more worried about what the other person is like than we are about how we interact with them. Of course, someone else’s traits will affect the relationship. But the unstated flaw is not the person or his or her characteristics, but of the relationship between these two specific people.

How can we use this to make dating life easier? The first step is try to figure out what it is that you want in a relationship. This requires you to be honest with yourself and not rely on other people as much. Hopefully, you should know how you feel better than anyone else. If you have trouble figuring this out, don’t despair. Think back to the people to whom you’ve felt attracted. What was it about those relationships that made them different? In my case, it was that I felt I could have both an intellectual and emotional relationship with the person. For you, it could be something totally different. What matters is that you try to identify what really makes you happy.

If a shadchan suggests someone to you, accept or decline based on your intuitions. When you interact with the person on the phone or on a date, feel first and think later. Let yourself go and be as normal as possible, then think if this is what you really want. If you can’t stand talking to the person, then that could be a negative indicator. If things don’t get rolling right away, you might want to give it some time depending on how you feel. If you’re in a relationship where you’re perpetually “not sure” where or how it’s going, don’t think “but s/he is a great person,” but think about your relationship. If you’re rarely comfortable with the person, then you either need more time or you need to move on.

For most cases, it seems to me to be the most useful method for assessing dates and longer relationships.

Final Response to the Shadchan

Shadchanim and others often don’t realize that you are entitled to your own feelings and you have a right to be happy. On the other hand, this gets especially difficult if you yourself don’t know what it is that you feel. In my final e-mail to the shadchan, I partially expressed this point.

    Recently, you have suggested several people to me as potential matches, beginning with my only serious ex-girlfriend. Although we discussed the matter briefly, I think that it might help if I elaborate on some of my feelings.

    First, I will admit that I’ve always been skeptical of professional shadchanim. Unlike friends who try to set me up, shadchanim usually do not really know me. Consequently, few suggestions could really be classified as a “good match.” rarely have a sense of what would be a “good match.” It’s difficult for a shadchan to be looking out for my interests when s/he does not pay attention to what my interests are. Even when I try to specify what it is that I’m looking for, I often find myself being ignored and shadchanim set me up with people based on their own perceptions or desires, not mine.

    Regarding X, I could understand you suggesting her if you had forgotten that we went out. Obviously, since we had dated for a year then it certainly would have made sense to suggest it. However, it is inappropriate to persist in pushing this suggestion once you know that we had dated for a relatively long time. In addition to the year dating, X and I had been friends for a few years prior. Unlike a typical one or two shidduch date, we do know each other quite well and we both invested a great deal in the relationship. If it didn’t work out, then one could assume that there were issues serious enough that they would not simply be resolved by someone suggesting “oh, why not try again.” If anything were to change that would be a discussion exclusively between me and X. I realize that you are also looking out for X, but when a shadchan makes a suggestion, s/he should be concerned with both parties, not just one.

    I realize that as a professional shadchan you’ve had much success in setting up people. Whatever system you use or intuitions you have obviously worked for many people. However, I also recognize that I am not a typical single. Unlike many people I’ve met I’ve thought extensively about who I am and with which types of people I’m most compatible. I try to be honest with myself as to who and what I’m looking for, and I have a fairly accurate intuition about whether or not a suggestion is a good idea for me (and especially after a few phone calls). In general, I like knowing before hand some reasons as to why someone thinks I’d be good for her as well as why she’d be good for me. Not only does it help give me a better idea of the person, but it also helps my understanding of the shadchan and how well s/he really knows who I am and the type of relationship for which I am looking.


In the end is anything easier? No one can create the perfect mate, and we are all vulnerable to unrequited love. What I hope is that for those still dating to think about what made you happy. What was it about those people. More than what, how did they make you happy. When you have an idea of what relationship you’re looking for, then you can try to find people with whom you would most likely find compatibility. If a shadchan sets you up, use your intuition based on what the person tells you.

In terms of finding people, go through the traditional routes of networking and even some of the more high-tech ones. Despite my experience, SawYouAtSinai is still a great tool for getting your name out there. Your own experience will depend on the particular shadchan you use, just like in real life. If you don’t want to go through a middle person, browse Frumster and see whom you find.

Whatever the case, remember that a relationship is about two people and their feelings and interactions with each other. Because of this, you should never forget that you are entitled to your own feelings. You don’t need to be pushed or forced into a relationship where you’re not happy. You don’t need to rationalize why he or she is not your type. It is up to you to sort out your own feelings, and it is up to you to act on them how you see fit. Once you’re in a positive relationship then the two of you will need to work together to maintain what you have.

All this might seem obvious, but I haven’t heard anyone articulate it. Unfortunately, it is the obvious which often gets most ignored.

Throughout a marriage, characteristics and people can and will change. Looks come and go. Interests mature, regress, or change. As life throws its many curve-balls, what will hold a marraige together is not whether someone is “intelligent” or “nice.” Ultimately what will make a marraige work is the relationship that two people share. If people are satisfied in their relationships – whatever needs they have are satisfied – then the marraige will be able to sustain.

This is just my take on dating and marriage. If you find it useful or helpful, wonderful. If you don’t, find something else that works for you. After all, that’s really the whole point of this post.

1. Not that people haven’t tried.


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