I can’t remember whether or not I’ve posted this theory of mine here, but here goes.
I believe that a lot of this problem comes from the fact that it’s typically mothers who teach their sons how to attract women. They don’t explicitly sit us down and give us a lesson on “How to get a girl”, but they teach us indirectly by making comments here and there about how certain modes of conduct will make girls like us, or praising our attributes (real and imagined) that girls will like. For me, this type of “instruction” led me to believe the following:
“Girls/women will be falling all over me because I’m (A) handsome, (B) intelligent, and (C) talented. Combine these attributes with gentlemanly behavior, and I will be irresistible to women.”
While that belief may look good at first glance, it makes one glaring omission: making an effort to actually pursue a woman. It’s somewhat embarrassing to admit that I was honestly convinced that, due to my attributes (A, B, and C), and the fact that I knew how to be a gentleman, the women would be pursuing me. No effort required on my part! As you can imagine, this resulted in a certain amount of disillusionment on my part once I was an adult.
If the father has anything to say on the subject, it’s usually to just to half-heartedly confirm what the mother has said, and maybe mumble something about not getting anybody pregnant until you’re married. Dad’s not going to disagree with Mom if he wants any sex for the next month, after all 
The problem here is that mothers tend to become historical revisionists when it comes to telling their sons what attracted them to Dad. My mom was raised by a chronically-unemployed, alcoholic father, and her mother pretty much supported the family. My dad, on the other hand, was raised by a father who owned his own business and was a hard worker who supported his family well, and dad’s mom stayed home and raised the kids. According to my mom, she chose my dad essentially because his family was exactly the opposite of hers. In other words, she actively picked him out from the available choices. This is according to her, of course. My dad never weighed in on why he picked my mom.
Now, Mom actively dated one other guy in high school besides my dad, but chose my dad over the other guy. She chose Dad for the reasons explained above. But the other guy (whom I’ve met, and who lives in the same town I do, nowhere near the town where they all grew up) seems to me to fit the criteria she taught me (handsome, intelligent, and talented) far better than my dad, which makes me go “huh?”
What my mom never mentioned when describing why she picked my dad over the other guy:
The other guy was a scholar. My dad was a halfback on the football team. My dad was a brawler. My dad joined the Marines. The other guy was polite and well-spoken, and went off to college. My dad was (and is) a loud, opinionated, boorish asshole.
My dad is a now-retired cop who could never afford anything beyond the basics for our family (though strangely always had enough money to buy new guns for his collection) and who left my mom after 32 years of marriage and ran off with a much younger woman.
The other guy owns a large corporation, is a millionaire who sent one of his kids to Princeton and his other kid to another good university, and is still married to the same woman he married after high school.
So looking back and analyzing the situation, it looks like my mom was actually attracted to my dad because he was aggressive, strong, and self-confident. But once she had a son (me) she unconsciously transferred all the other guy’s attributes to my dad and presented those to me as “what attracts a woman”, while never mentioning the real reasons she was attracted to my dad. And then she did everything she could to make sure I didn’t turn out like my dad, which was easy to do since Dad pretty much left all the kid-raising to her. Overprotective, self-deluding, idealistic mothers do not produce sons who are attractive to women.