A guest post by JS:
I was thinking about my post regarding "speed" dating - in which people are pressured to make a decision on getting engaged/married quickly, usually within 8 dates (often less). It occurred to me that the number of dates isn't really the problem - it's an element in a larger problem. After all, even though my wife and I dated for several years before getting engaged, the reason for this was practical - we didn't want to get married in college and we wanted to be self-sufficient once married. We actually knew (or had a very strong idea) within a few months that we were in this for the long haul, so to speak. Similar story with my brother in law who was recently married: when he met his future kallah they both knew within 3-4 dates they wanted to get married, though they dated longer before getting engaged.
So, this got me thinking that a short courtship period isn't the main problem. I think the problem with the shidduch system (or yeshiva/chareidi culture) is the way that it infantilizes what are supposed to be adults entering into an adult relationship. This is apparent in many ways in both the yeshiva/chareidi culture and in the shidduch process.
From a young age, the yeshiva/chareidi culture separates children from their parents. Yeshivas have long hours, which become even longer when the children are older and night cheder is imposed. Yeshivas typically have school on Sundays. Many children are sent away to dorm at the yeshiva even when the parents are nearby. The yeshivas create a completely immersive environment in which all outside influences that may interfere with the yeshiva's hashkafa and education are shut out - including parents. Kids are kept away from home on numerous Shabbatons to rebbe's houses or to visit other communities. In the summer, kids are not allowed to be at home where there may be bad influences. They are sent to summer camps for continued learning. Even later, when kids are off for bein ha'zmanim they are shipped away immediately to kollels or shul learning programs to sustain the level of immersion. This creates a situation where, especially for guys, no one is showing them how to grow up, mature, or be responsible. No one is teaching them how to be an adult. Most importantly for the topic at hand, no one is teaching them how to relate to the opposite sex within the context of dating/marriage. Being able to sit still for hours on end and understand a gemara is not maturity - or at the very least, isn't the maturity necessary for a relationship.
Similarly, in the shidduch system the attitude is everyone else, all of the adults, know best. The "kids" don't know any better and can't be relied upon to know what's best for themselves. The adults do all the legwork, all the investigating, and all the representations of who their child is and what he/she is looking for and the child sits back and just says yes or no after a dinner date. The message in all of this is clear, you're too immature to be trusted with such an important decision. And, in a self-fulfilling prophesy, the already developmentally stunted children tend to focus on all the wrong things in a potential mate.
Saddest of all, this infantilization continues even after the kids are married through parental support which almost always comes with parental conditions for how the children should lead their lives.
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