Just Smile:
You write’ “but those families aren’t on your radar of shidduchim – so it doesn’t make a difference to you that a more modern girl gets engaged – she wasn’t on any of your lists”
I’m not quite sure why you think “modern” girls aren’t on any of the lists. Last I checked the shadchanim and organizations that I’ve spoken to deal will girls from all backgrounds and styles provided they are orthodox. This shidduch crisis exists very very much in the “modern” (I hate labels but you used them) crowd.
As for you first point. That brain lock
“most people see it as a negative if the girl has been going out for a few years and still not married”
is exactly what needs to be countered. There are so many regular normal great girls 21-24 (and older, I’m just using those ages as the initial stage) who have BARELY dated. It is absurd to think that if she isn’t married yet, there must be something wrong with her. B”H as a result of the publicity and discussion of the past year, many many boys have gotten married to girls who are close to their own age. AND guess what? They realized that the silly arguments put forth to NEED a much younger girl are just that, silly.
(That’s not to say that for some boys the right girl for him will be a couple years younger. The issue is correcting the misconception that EVERYONE needs to marry a girl much younger.)