The Matchmakers’ Chronicles
By: Michele Herenstein
Published: Thursday, January 31, 2008

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“To be Hashem’s shaliach (emissary) in bringing two people together is such a special thing. It is something that I have always wanted to do, but it is a little bit more difficult to do as a single person. Now that I am married, I am able to participate in group matchmaking endeavors, which give me more of an opportunity to meet singles who aren’t in my network. The more people I know or have access to, the better the odds are that I will be able to make a match.”

These were the words of Alison (all names changed for privacy), who dated for 15 years and has been married for a little over one year. She was one of the many matchmakers who were helpful in describing their difficulties, their frustrations, and sometimes their joy in being able to help singles by becoming matchmakers after many years of their own, often difficult, dating situations. Alison and her husband had been set up by a matchmaker through Saw You at Sinai (an online dating site), and she describes the matchmaker as being “very helpful—just the right amount of involvement. She was single for a long time so she really had a good sense of how to be helpful.”

Most of the other matchmakers I contacted had dated for long periods as well, such as Dalia, who had dated for almost 20 years. “I started dating when I was about 18 or so, but thinking back on it, I may not have been ready to get married. Finally, when I was really ready, there weren’t that many ‘good guys’ left. But I am not one to give up. Although I may have questioned once or twice over the years whether Hashem really had in mind for me to get married, I knew deep down that there was no way in the world that I wouldn’t meet someone who was for me. Finally, when I was 37, a shadchan (matchmaker) had an idea for me. He was No. 239 (on my list of all my dates) and at the end of my long list, I finally wrote, ‘The End!’”

Laura, who had dated for 16 years before getting married, describes dating in her twenties as being fun, but in her thirties as being depressing. She and her husband, who were set up by her mom’s friend and her husband’s aunt, have been married for six years. Laura didn’t have a matchmaker during the dating process, but tells of a friend who acted as a coach. “Obviously my dating instincts for the past 16 years had not been right, so I needed to change something. I firmly believe that I would not be married today were it not for her. She helped me stay sane and helped temper my instincts so I didn’t scare my husband away.”

She goes on to describe how she had never had the ambition to become a matchmaker but saw how huge the dating problem was and felt the need to help out in some way. Laura is now a matchmaker on Saw You at Sinai and attends separate shidduch (matchmaking) meetings as well.

I thought that being a shadchan would be relatively easy for these “newly” married couples, because having dated for so long, they would have a good sense of how tough it is to be single, and have more compassion for the singles longing to get married. However, there were a myriad of emotions that were expressed that I previously had not given thought to. Laura tells how being a matchmaker is very frustrating: “It’s like dating all over again. I get depressed when things don’t work out or when I realize how many great people are out there and still single, though they want to get married. The saddest part is that men want younger women and women don’t want a man 20 years their senior.”

Josh dated for 10 years, and now, after being married for less than a year, has already become a matchmaker together with his wife; he describes them as a matchmaking team. Josh and his wife found their dating process to be extremely comfortable and fun. He says, “I think that a lot of that comfortableness can be attributed to the two of us being a bit older than what is generally pushed in our circles.”

“We haven’t been doing matchmaking formally for that long, but we are so happy to have the opportunity,” says Josh. “The one thing that is striking to us is how many singles do not follow through. It is hard to think that these individuals are truly committed to being in a meaningful relationship when they don’t respond to match suggestions or never initiate contact with a mutually approved match (on Saw You at Sinai) whom they indicated they wished to date. I think that a lot of dating frustration could be alleviated if people used common courtesy. If you say you’re going to call someone, you should follow through and call them.”

Jen dated for nine years before getting married and admits that she didn’t always aspire to be a matchmaker. She’s presently on hiatus from working on Saw You at Sinai, but tells of some of the things she learned from matchmaking, such as “learning to separate my own interests and expectations from what other people (singles) want. Even if I found it offensive that 45-year-old men wanted to date only women in their twenties or early thirties, I had to realize that there might be women who are okay with that and that is their business. My job was not to judge or choose people who I thought were ‘catches,’ but find people who might be compatible with each other.” Jen goes on to describe the difficulty of dealing with certain singles. “I found it hard dealing with people with bad dating skills; the usual not-calling-each-other-soon-enough, saying offensive things to each other on the phone, playing ‘games,’ or being overly sensitive or reading motives into harmless actions. It was just frustrating that people couldn’t get over these hurdles, but I’m not their therapist, just their matchmaker.”

I wondered whether these matchmakers actually enjoyed setting people up, or whether it was something they did because of experiences they had gone through themselves while dating, essentially feeling the need to give back. Alison admits that she “matchmakes” out of a sense of responsibility. “I have a lot of single friends and I know how painful being single is. I desperately want to see others find the happiness that I have found. I don’t feel comfortable just ‘sitting here’ while I know others are suffering and I may be in a position to help them. It is very time-consuming and at times can be difficult, but if I can just help two people find their zivug (partner), I would be so happy!”

Josh tells how he and his wife are matchmakers because “it makes us feel good to put people together in a meaningful way. Along the way, we feel that it is important to get feedback from the individuals to understand how things are going and to offer non-judgmental and empathetic guidance, as there will always be some bumps in the road. The key is in the two people in the dating relationship being able to truly express their wants, needs, or feelings and for the other to respond accordingly. We, as matchmakers, try to help facilitate this and to possibly give alternate perspectives for viewing a situation.”

Dalia describes her impetus in becoming a matchmaker. “When I was dating, I often said to myself that someday I would love to do this (be a matchmaker) for other people. I don’t do it because I feel I have to; I do it because I do know how hard it is to meet, and I truly love doing it. If I didn’t also have a full-time job and a family, I would put a lot more time into it.”

Deena had dated for approximately eight years, has been married over two years, and admits that when she began dating, she wasn’t ready for the “right” man to come along. She describes the dating process as being overall an enjoyable one. “Every date made a good story and I truly believe helped me narrow down what was really important to me. Also, it made me appreciate and recognize what I found in my husband.” She describes setting up many people over the years and tells how sensitivity on the part of the matchmaker is so important, having learned this from her own dating experiences.

I asked Deena how she felt about matchmaking, and she said, “It’s amazing when you hear it was a good date and then there is another. It’s me’ein Olam haBa (like the World to Come) when you hear of an engagement and are dancing at a wedding. It’s so rare when that happens. All along the way it is extremely time-consuming and often frustrating—especially when you disagree with people’s logic/reasoning/criteria for not agreeing to a second date.” Deena is not convinced that she has any special talent, but she does feel it’s the least she can do to “encourage two people to meet—and who knows what wonderful things can come from it.”

Singles often aspire to “matchmake” in earnest as soon as they get married. And matchmaking is a wonderful chesed (act of kindness) to undertake. But at times, it’s obviously difficult, time-consuming, and frustrating, as told by several matchmakers above. But is the joy of a successful shidduch worth the effort? I would hope so, but every person has to decide that for himself or herself. I remember a couple who I set up many moons ago. The feeling of complete joy while dancing at their wedding, and the delight I felt over the years as each of their children was born, has never gone away. Matchmaking doesn’t always turn out “happily ever after,” but achieving many of the best things in life often takes much effort.

I’ve had good experiences with matchmakers—and negative ones, as well; but I’ve never doubted that the matchmakers helping me had anything but the best intentions. Singles may not always like every matchmaker they work with, and I’m sure not all matchmakers feel close to each single they assist. But we’re all in this together, and hopefully singles and matchmakers can learn from each other and the respect and sensitivity that should be shown by both the singles and the matchmakers towards each other will always be there. If we want Hashem on our side, helping us in our endeavors, whether it be with matchmaking or with dating, we must be willing to show we are worthy of His help.

So kudos to the matchmakers for all of their hard work, and good luck to the singles who will hopefully prosper in dating and meet their zivug very, very soon. v

Michele Herenstein is a freelance journalist who lives and works in New York City. She can be reached at

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