In Search of the Elusive Chupah

By Marcia Kesner

A professional counselor offers insights on patterns — in thought, behavior and our society — that keep singles from marriage

She applies her lipstick and gives herself the once over, vacillating between mild anticipation and utter dread.  Another date. Over the years, she has lost count.  The dates have all become a blur – phone call, dinner, pleasant, superficial conversation and a promise to be in touch.  When this one called to ask her out, the phone conversation went smoothly enough, as many of them did; yet all the others ended in disappointment.  Her friend at the office, who just happened to be his aunt, described him as “cute as a button, charming, a mensch, and he makes a nice living.”  She dreams of George Clooney with a yarmulke.

He stands at the door, tentatively.  “Where is she?” he wonders, “my Cindy Crawford with a fabulous cholent recipe?”  Over the years and somewhere along the way, his hopeful expectations soured and he began to approach each date as a task to complete, just another step in an endless, disappointing process.  He has almost resigned himself to the idea that he may never marry.  For some reason, God will not provide him with a mate — not one in which he’s interested anyway.  But “You have to keep trying,” they tell him. “You never know when the one who’s bashert [intended] for you will appear.” His aunt described her as “blond, thin, in her early twenties, bubbly and vivacious.” Cindy, where are you? He rings the bell.

Illustrations by Caryl Herzfeld

Illustrations by Caryl Herzfeld

There they stand. Awkward and polite. She is struck with the reality that he is a little older, shorter, balder than she had imagined and, at first glance, doesn’t appear to be “the one.”  He notices immediately that she is not thin. The “blond” hair is sort of mousy brown and she looks closer to 35 than to 25. What his aunt described as “bubbly and vivacious” quickly begins to sound loud to him.

They muddle through dinner, both somewhat relieved that there appears to be a mutual disinterest.  Neither wants to prolong their apathy, both declining dessert or coffee. He takes her home. She thanks him for the date and sprints for the door. Once inside, she quickly calls a single friend to share the latest chapter in her war story journal.  He drives home, mentally tallying up how much money he has “invested on dates” over the years, and ends with his usual hopeful refrain,  “Maybe the Yankee game is still on.”

Unfortunately this scenario is all too common.  Courtship and marriage — what once was a fairly simple process in the Orthodox Jewish world, has become a major cause of frustration and concern to singles, their families and communities.  How has this phenomenon occurred which, by many accounts, is taking on epidemic proportions?

A World of Choices
First, we must acknowledge that we live in a modern, secular society where lifelong singlehood is not always a cause of distress or perceived as a state of incompleteness.  Despite attempts to maintain our uniqueness and customs, Orthodox Jews are constantly exposed to messages in the popular culture implying that singlehood throughout one’s lifetime, with its ready availability of money, independence and physical intimacy, is a viable option and may be even preferable to the stress, struggle and compromises involved in close interpersonal relationships. In our modern society, a premium is placed on personal freedom. Autonomy is valued and encouraged.

Sadly, many singles view available partners as just that:  a commodity. 


Another factor that reinforces singlehood is that shuls and other Jewish institutions, which used to be the social domain of married couples, now welcome single participants. I hasten to add that while this admirable inclusiveness helps singles feel a part of the community, the flip side is that it lessens the urgency once felt to marry and become part of a couple. In many communities, singles have developed their own chevrah with other single friends. These groups serve as a pseudo-family and afford singles the opportunity to create a support system in a less formalized or traditional way, without the obligations of marriage. This too has psychological advantages, yet contributes to the comfort level of being single.


We have been taught to believe in a limitless supply of almost all commodities.  Sadly, many singles view available partners as just that:  a commodity. In previous generations, when our ancestors lived in shtetlach, entire communities knew just how many single men or women were available. Singles were matched up at an early age within the framework of a finite number of options: reasonable expectations could develop and choices could be made accordingly. In today’s world, if one is unable to find a suitable spouse in his or her own backyard, ease of travel and communication offer an entire world of possibilities. If your basherte is not in the neighborhood, why not explore another community, or even another country?  In the minds of many, there is always an available and ready supply of potential mates.  “Why the rush?” to find a spouse, when there are always other choices out there?

The Terrible “Toos”

Even though lifelong singlehood is contrary to the basic Jewish way, some singles continue to feel ambivalence towards marriage.  These people often maintain that they would like to marry, but never seem to find an acceptable partner.  They go on date after date, but the candidates never seem to possess just the qualities they are searching for: their idealized mate remains ever elusive. “He’s too religious” or “She’s not frum enough” they relate. Yet when presented with another date more commensurate with their hashkafah, these singles curiously find that the new suitor is conversely “too lax” or “too frum” (and often point to trivial details to bolster their claim).  These singles are searching for a romanticized illusion, which remains ever-perfect in their minds. The true problem often is not the level of religiosity. But no one can argue with a single when he/she reports that a potential partner is “too ___,” inferring that to accept this person would require a corruption of one’s religious standards.

In addition, as frustration with the dating process grows, their fantasy “perfect spouse” becomes more and more developed.  Fantasy becomes increasingly important to their internal self-concept, and the need to justify their long wait for an idealized partner grows even more significant.  How could they possibly consider compromising their ideal — “settling” for the imperfect person they are now dating, when they have waited so long?  Unwillingness to compromise from their vision of the ideal makes certain that no partner is ever sufficient for them.

Falling in Like
To break this cycle, one must be able to emotionally override the attachment to the fantasy ideal. Enough time must be spent to achieve an emotional bond which would supplant the ideal. Generally, the longer one has been single, the more time it takes to form such a bond.  Yet relationships take time to develop, and this element is often missing in religious dating patterns. There is pressure to commit to the shidduch after only a few dates, or break it off.  (Is it any wonder that it is easier to say no?) But if the couple maturely decides to take the time, an attachment can form — and once it’s in progress one notices positive traits which may not have been apparent at first glance.  Somehow, the “checklist” traits of the ideal previously required seem less important. Love may not yet be in full bloom, but considering this person for marriage now becomes a viable possibility.

Staying Safe – and Single
For some,  the anxiety produced by new social situations or repetitive rejection is more disturbing than the familiar feeling of being alone. They begin to acclimate themselves to the familiar. While aloneness is not always gratifying to these people, it is certainly familiar and feels comfortable and safe.  It is easier for these singles to find confirming data to “say no” and cross off another candidate to alleviate their anxiety, rather than continue the relationship and experience the anxiety of a relationship they may not feel able to control. These singles need to discover the source of their anxiety (perhaps with the help of a therapist or a good friend) in order to lessen it and take new risks in socializing without the fear of rejection or disappointment.

There are other issues, of course. For example, “fear of commitment” often can be translated as fear of failure in choosing the right partner. Children who are exposed to unloving relationships (sometimes observing their parents, neighbors or friends) may conclude that the risks seem too high.  Others fear making a wrong choice and passing up a more desirable partner down the line.  And still others have a fear of intimacy based on low self-esteem and more complex psychological issues.

wish list

Revising “The Wish List”
How can you, as a friend, relative, or rabbi make a difference? In today’s world, the standard suggestion is often, “Go see a therapist.” While therapy is often very beneficial, a trusted friend can sometimes accomplish the same goal. If you are a trusted person in a single’s life, you can have a profound impact. When asked for your help, encourage your single friend to explore his/her dating history and look for patterns. More self-awareness,  and a  candid “inventory” of strengths and weaknesses can help identify the attributes he/she should look for in a spouse. And what is the single looking for? Is your friend’s goal to satisfy genuine needs or superficial ones? Exploring within, we often find that we look for qualities in others that we do not feel we possess ourselves – and instead of working on developing those qualities ourselves, we try to acquire them through another person. With this possible self-delusion in mind, your single friend should now prioritize what is truly important, rather than cling to a wish list of desirable traits he or she would to “own.” What kind of traits would a potential spouse truly need in order to establish and build a loving relationship with your friend? Are other “frills” necessary? Must she really be a Jewish Cindy Crawford?

Honesty is the key. No one wants criticism, but assuring a single he or she is “perfect” – just oddly unlucky in love – will not bring the chupah any closer. For starters, a single who is serious about getting married should ask him/herself the “Questions for Reflection” on this page, then ask the same questions of you to gain your perceptions.  The gap between his or her self-opinion and your appraisal – offered as an honest, caring friend – may reveal the areas that need rethinking. A shortcut through that long road to the elusive chupah may yet be found!

Marcia Kesner is a Licensed Professional Counselor.  She is the Director of Specialized Treatment Programs at Ohel Children’s Home and Family Services in Brooklyn, New York and maintains a private practice.   This article contains elements from her presentation with Mordechai Zeiger on “Singles and Shidduchim: Attracting a Healthy Partner and Relationship,” at the Nefesh Conference of Orthodox Mental Health Professionals which was held in Baltimore, Maryland.

This article originally appeared in the Summer 2000 issue of Jewish Action.

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