Okay, time to air some of my thoughts about dating (again). Just some thoughts I have to get off my chest.
Shidduch dating seems to work well for many. You avoid a lot of the pitfalls of the non-shidduch world - you have an intermediary to help guide you through the process, you are not dependent on meeting someone randomly, and you have similar values and beliefs as the person you are set up with. However, as a person gets older without getting married the shidduch system seems not to run quite so smoothly. I think this is for a number of reasons, but at the heart of them, I believe the system encourages singles to halt the development of many of those skills that are so important to a future marriage.
As people get older, their personality matures, and they become more of an individual. Goals and aspirations are set and interests are pursued. All of this can make it more difficult to subsequently change gears and begin to think in terms of what is best for more than just oneself. And the consequence of shidduch dating is that because an individual is not accustomed to taking part in serious relationships, he or she does not necessarily develop the mindset of thinking about someone other than himself. I am not saying that I think being in a series of serious relationships will positively affect an individual's ability to sustain a marriage, but I do think that a drawback of being an older single in the shidduch system is that you tend not to cultivate the ability to think in terms of more than one's own goals
Another major problem I have with the shidduch system is that it seems very focused on finding a reason to reject someone. I find that often singles go out with each other searching for negative attributes that they cannot possibly live with. Rather, I feel that they should attempt to find the positive aspects of the other person that may very well complement and enhance their own personalities. I am completely not exempt from this - I have often found myself thinking that someone seems nice but... I just don't think I could handle this or that. Rather, I feel I need to be forced to look for the positive traits that the other person possesses and focus on those positives rather than the few negative qualities I can find. G-d knows guys will be able to find my negative attributes if that is what they choose to look for, so I know I should give them a break as well. Unfortunately I think this aspect of shidduch dating gets harder and harder as one gets older. I know that there are things I would have easily accepted in another when I was 20, that I just cannot tolerate now. And this list tends to get longer and longer as time goes on.
I feel the shidduch world also fosters a lack of maturity when dealing with major life issues. Hiding behind a shadchan is not a sign of being prepared to confront another person with issues that must be dealt with in a mature and adult fashion. And I think these skills must be cultivated in order to be able to effectively succeed in marriage. For someone who does not get married into his late 20's or early 30's, this lack of skills in dealing with another is going to have a negative impact on that relationship.
Like I said, I think the shidduch system works well for many, but those people are mainly the very young, and those who don't yet know themselves well. Because you are still learning about yourself at the age of 19 or 20, it is often much easier to grow alongside someone else. But once you move beyond those early-20's, and get more set in your ways, and are given reinforcement by your community to draw a longer laundry list of absolute musts and must-nots, I think the shidduch system begins to fall in effectiveness.
I don't know what the solution is, I think navigating the dating world is difficult no matter how you choose to do it. But I know that a system that encourages singles to postpone the enhancement of those qualities most important to a successful relationship until they are actually committed for life needs to reevaluate something.