Matchmaker make me a match

When my wife and I were newlyweds, we took up an informal study of marriages. At the time, my parents had a close circle of friends, eight couples who got together regularly. We studied each couple to try and discover the “secret” to a happy marriage. After a while, we compared notes and found that we had both reached the same conclusion: each couple was mismatched!
Couple one: She was too smart for him… Couple two: He was too frum for her… Couple three: She was too sophisticated … And couple four: He was too loud. Had either of us been the shadchan, we would never have put any of them together. They just didn’t match up.
Our little exercise brought home a critical point: A successful marriage isn’t a match of two similar individuals. It is a union of a man and woman, each with their own temperaments, emotional makeup, and personalities. Each comes in with unique strengths and weaknesses, and as a couple they complete one another. His deficiencies are compensated for by her strengths; her shortcomings are filled in by his positive attributes. The whole is much greater than the sum of the parts.
But knowing exactly what your strengths and weakness are and how to correctly balance them is far from simple.

Marriage is a complex weave of human personalities, attributes, and attitudes. Before a person can know what he needs in a spouse, he has to know himself. He has to be able to answer some fundamental questions about his personality: “Who am I? What really makes me tick? What are my core tendencies, strengths, and faults? How will I react in different life situations? How do I handle stress? What about failure? What about health issues? What if I lose a child?”
Most people don’t come to this level of self-awareness until they’re old and grey—and even then, not everyone does. How can we expect a young person, just starting out in life, to have such a deep understanding of himself?
But the problem is more severe. Let’s assume that somehow I do know myself. To find the right match, I have to know which attributes will complement my own. Do I need a person with a strong personality or a mild one? Do I need a leader or a follower? One man may need a woman who believes in him, and another may need one who will put him in his place. But which man needs which type of woman, in what balance, and to what extent is very hard to know. As an example…

One day, before giving shiur, my rebbe, HaRav Henoch Leibowitz, zt”l laughingly remarked, “Baruch Hashem! We finally found a shidduch for that fellow. I didn’t know who we would marry him off to. What a temper he has! But, baruch Hashem, we found the perfect match.”
At that point, while none of us knew who the rosh ha-yeshiva was referring to, we were very curious about the “perfect shidduch” for a person with a fierce temper.
The rosh ha-yeshiva, zt”l, continued, “We found him a woman with a temper even bigger than his. Now when he opens his mouth, she screams louder, and he’s as quiet as a lamb. It’s the perfect shidduch.”
While this is a cute story, everyone knows that the worst match for a man with a temper is a woman with a bigger temper. It’s asking for the next Hundred Years War…unless he only talks a big game, but is docile deep down. If his spirit is really meek, then he won’t explode when confronted. Actually, quite the opposite—he will simmer down. In that case, the ideal match is a strong woman.
But who has the wisdom to make that judgment call? Who has the life experience to know whether his inner essence will comply or rebel against such force? Certainly no other relationship requires that type of insight. When it comes to choosing a friend, the criterion is simple: do we get along? If yes—great. If not, then let’s move on.
A marriage, however, is multifaceted. It entails taking two people who are diverse in nature, temperament, and upbringing, and asking them to mold themselves into one unit. Choosing the right partner requires a level of genius that the average person simply doesn’t have.
In fact, most people don’t even understand marriage.

Ask couples that are married for twenty years or more to explain the “secret to a happy marriage.” Ask them to define why some marriages work and others don’t. Why do some couples flourish and others fail?
Likely, you will get a string of answers, with most honest people admitting, “I really don’t know.” And if you do come across some people who are offering theories, just ask them to explain why many nice, considerate couples are at each other’s throats—and plenty of coarse, selfish couples manage to get along just fine.
What you will find is that the average person can’t explain these lofty mysteries because the dynamics of a successful marriage are very elusive. And even highly intelligent, worldly people can’t define the “mechanics” of why a marriage works—or, if it doesn’t, what to do about it. So how can we expect a young person who has never been married to know what he or she needs in a marriage when even older married couples can’t figure it out?
If the situation isn’t sounding difficult enough, there’s a far bigger issue at stake.