While I don’t have the solution to the shidduch crisis, I think there are several factors that have contributed to the situation:
First, there is the issue of going out with more than one person at a time. I know that the Rabboninim have come out against multiple dating, however, if he is free and she is free, I don’t think there is anything wrong with going out for a look/see first date. Many a girl has lost out because she had already said yes to person #1 when another suddenly became available and she had to say no to person #2. Then, by the time she goes out with person #1 and it’s a no go, and she wants to move to person 2, he is no longer available because he moved to the next girl on the list. Months and months are wasted waiting for person 2 to become available again or for another shidduch to materialize. By the time a girl is 25, she could have lost out on a number of shidduchim because of timing.
Also, because person #2 has been suggested and may sound more interesting than person #1 and because the girl might think person #2 is in the wings waiting, she might not give person #1 the same attention she might otherwise have given him had person #2 not been suggested. So she goes through the motions of going out with person #1 and rejects him, thinking person #2 is on the horizon, but by that time, person #2 has moved on to the next prospect on his list. So she is left with no one.
The second factor that has contributed to the shidduch crisis is the tremendous peer pressure to marry a learning boy. There are many fine learners out there who opt for various reasons to go to college and still have a seder at night. These YU types are many times written off and not even considered and many a fine bochur is missed out on because everyone wants “the best boy in Lakewood.” Each potential shidduch should be evaluated on his or her own merits but many times people use their checklist and if he or she doesn’t meet all the requirements, they are rejected. Years down the road, the bochrim and the girls would be thrilled with some of the suggestions they rejected when they were younger.
We need to be a little more lenient permitting girls to go out with more than one shidduch at a time when it is a first look/see date. Much time is lost otherwise.