The Mind Of A Matchmaker

Everyone seems to have different opinions about the shidduch “system.” Women blame men, men blame the women, everyone blames everyone. About the only thing people can agree on is that the situation stinks. Some of you may be familiar with Chananya Weissman’s www.EndTheMadness.org which attributes the problems to misguided perceptions of dating and improper assumptions of Jewish law. Following his impression, Chananya provides general solutions and even formulated a covenant for singles to follow to break the cycle of “social insanity.” While there is much truth in Chanaya’s analysis and solution, I find that his construction of the problem does not offer practical alternatives for singles. It is an important first step in fixing many of the horrible misconceptions that Orthodox Jews have about dating, but it alone will not help. Furthermore, as this post will show, his assessment is limited to a certain type of stupidity when the problem is with how people view dating and relationships in general.


Loyal readers of the site know of my own difficulties in dating in the Orthodox world. I fully admit that I am hardly an expert on love and relationships, and I’ve experienced more than my share of disappointments. Without starting a flame war of who is more to blame, I’d like to try to re-frame what many people already know and explain why things work the way they do, and offer an alternative mode of thinking. Before I get to my own perception, I’d like to relate the following anecdote.

A little while back, I had a negative experience with the online shadchan network www.SawYouAtSinai.com.1 At the persistent suggestions of some friends, I signed up for the free site. After you complete a profile, you chose one primary shadchan and up to two secondary shadchanim. One of my three choices was someone who is very highly regarded, and I had even worked with on one occasion.2 Within minutes of confirming my selection of her, I get an e-mail saying that the shadchan has a potential match for me. So I’m thinking she really is good, or at least is really serious about setting people up. So I log in to see whom she considers to be an appropriate match:

My ex-girlfriend.

Some general background here is in order. After knowing this person for several years, we decided to go out, and we dated for almost a year. This was hardly a typical shidduch which lasts a maximum of 4 dates. We got to know each other really well during this time, and for whatever reasons, it didn’t work out. After investing much time and emotional energy in this relationship, still decided it wasn’t right, a shadchan decides that it’s a good idea for us to date again. Knowing the ex had nothing to do with this, I was annoyed at the shadchan.

Frustrated, I let the e-mail sit for a while and focused on school assignments to calm down.3 Then I get the following message:

    You never got back to me if you would be interested in meeting X, I think she would be a perfect match for you. She lives in [deleted] and she is a great friend of mind. From your profile it seems it would be perfect, except maybe for the Isreal [sic] issue, but we can work on that.4

    Please let me know your thoughts.

By this point, I had calmed down. I gave the shadchan the benefit of the doubt – perhaps she didn’t realize we had dated for a year and is making an honest suggestion. That we dated for so long would indicate that it would obviously be a legitimate suggestion. So I politely reminded her.

    Also, I know X; we dated for almost a year. In fact, I met you one Shabbat when X and I visited the [deleted].

My thought was that now she has two plausible possibilities. Either 1. move on and look for someone else or 2. inquire as to the nature of the relationship to get a better understanding of who I am and for what I am looking. Of course, we got option 3. Abject cluelessness.

    Does this mean you are not at all interested in pursuing X!! Any hope there?????????

The shadchan persists fully knowing that we had an extended serious relationship. I respond as follows:

    This is not an issue of me pursuing X. We tried, it didn’t work out. Unless you would have a detailed understanding of what was wrong and a reasonable expectation that things would be different, there doesn’t seem to be a point in trying again.

If the shadchan understood the relationship, and could give a reason why things would be better, I’d be open. Of course, at no time did the shadchan take the time to ask me about the relationship.5 Ignoring my last e-mail, the shadchan writes:

    To be completely honest, I know X very well and I would love to talk to you about it. I would not do it over the e-mail. My phone # is [deleted] or I can call you which ever you want. Just let me know.

The next day, she leaves a message on my cell phone.6 Now, I’m just livid. Cooling off some more, I call her back the next day. Oblivious to my previous e-mails, she simply says that she thinks we should try again. No understanding of the previous relationship, no suggestions for how things would be different, just simply “give it another shot.” I politely explained that there didn’t seem to be a point, and quickly got off the phone.

Some suggested to drop the shadchan and move on, and in the end I did since she obviously did not have my interests in mind.7 Friends of mine know how upset I was at this point. Not at the ex, who I stress is completely innocent in all of this, but at the shadchan and her mentality of dating and relationships. Next post, I will offer my interpretation of what happened here, why it’s endemic to most singles, and some suggestions for improvement.


1. I’m not the only one; check out Meredith’s recent misadventures.
2. She had suggested a person, whom I later met by chance at a Shabbat meal and we never actually went out. Skipping bizzare and juicy details, a mutual friend told me afterwards, “Yeah, I also thought of setting you guys up, but then you met each other.”
3. How sad is that?
4. One of our issues is that I plan on making aliyah eventually, while she does not. Based on conversations and experiences, I’ve realized “work on that” is really a code for “we’ll make you give in eventually.” As an aside, I’ve been working on my thoughts about dating an aliyah, and should be posting that shortly either here or at Kumah.
5. In fact she later said, “I don’t know, I don’t want to know.”
6. I gave it as contact info for my profile.
7. When she told the ex of this story, she added that I shouldn’t even be on the site in the first place.

Posted in Jewish Dating.

14 Responses