The problem with the shidduch/dating world is our attempt to apply a “best fit” practice to something that nothing will really fit.
In an ideal world, dating won’t really exist. Everyones’ parents and rebbeim will know them nearly perfectly. Dates will be determined via parents speaking with the other set of parents. The guy and girl will meet for an hour, or so, and the shidduch is decided.
In close knit Chassidish communities, criticize them as you may, this actually works out very well as the people in those communities are generally more products of the community than your average Yeshiva Bachur or Bais Yaakov girl. Meaning, that once a Chassidishe boy or girl is adequately described, you can get a good enough sense of what type of person they are and what type of person they would be good for. In most communities, though, this is far from the case as there is much more variation in what people are doing and want to do with their lives along with variations on Hashkafa.
Unfortunately, due to that high amount of variation, it’s not always so obvious what a guy/girl needs and what they want to do with their lives. This requires a ridiculous amount of investigation and interview which often goes way further than required leading to the problems we face today.
(On a side note, I’ve rarely heard of the legendary boy who wants a Barbie doll in a Bais Yaakov uniform. They don’t really exist as much as people allege they do in most Yeshivas. The mother who wants a Barbie doll as a daughter-in-law is a whole nother ball game)