There are all sorts of generalizations about what men and women are really interested in when it comes to dating. Phrases like "men only care about how a woman looks" or "women only care about money." Ridiculous or not, they all have a common theme -they come from experiences of people, and hold at least small kernels of truth. That kernel, I believe, stems from fear (and overreaction to that fear).
For example, physical attraction is important to men. No amount of trying to teach men otherwise or degrading how we experience attraction is going to change that physicality is important to us. Not that it should be (or is) the only (or highest priority) thing men care about in a woman or marriage, but such a conclusion may be implied by people who have experiences with men where they put too much emphasis on physicality (and seem to ignore everything else) or people who overreact to that basic part of men.
But why, oh why, does a man need to know the dress size of a prospective woman's mother!?
My answer is not that he needs to know, but that he is concerned and afraid. So much that sometimes we each ask ridiculous things in trying to calm our own fears. In this case, it is a fear of the prospective woman gaining significant weight after marriage, or not working on it after having children (and thereby becoming unattractive to him). I think men need to realize that women do gain weight when they are building a child (with God's help, of course) inside their bodies. But their concern, I like to believe, has to do with still being (physically) attracted to her.
Is it legitimate to fear that? Well, if a man is no longer attracted to his wife, that can cause significant marital distress. However, being that I'm not a stickler for numbers and don't think that attraction (even physical attraction) is strictly a matter of pounds and dress sizes, I see the method of trying to handle that concern as absolutely destructive (regardless of whether or not there are statistical analyses that correlate a mother's dress size to her daughter's future weight -and which I have not seen).
That whole issue (and what a mess they make of it!) becomes moot when a man and wife can be honest with each other. When a man can convey his concern without pointing fingers or blaming, and when two people are willing to work on themselves to better their relationship with each other.
The example of "women chasing after money," similarly has to do with a concern for security. I believe that women are not materialistic (though there are a tiny minority of cases the same way some men are far too fixated on pounds and dress sizes). In a world where money is the way we ensure our needs are met and our future is secure, it makes sense to have concern for lacking in that department. Not that it actually brings happiness on it's own.
I acknowledge that I have some of my own ridiculous and irrational fears when it comes to relationships and marriage. I hope to work on them, so that the legitimate underlying concerns may be addressed without becoming inflexible or ridiculous expectations or demands.