Our MC/IC couselor specializes in men issues and has taught college classes on men and relationships, stress, fathering, and sex. It has been interesting to hear his perspective.
In short, he believes many men do not grow up with role models who express emotion, instead it is more "what you do" verses "how does it make you feel". Therefore, we have all these boys who think being good at sports define them and then they grow up and it becomes their job and sex life that defines them. Other men feed into this, as there is this competition to being a "good" man which translates into earning money and have great sex. Emotionally, they are immature. They don't share what is bothering them, have no idea how to share it, therefore their insecurities grow and they start feeling inferior. As a protection, this can turn into almost a narcissistic/selfish attitude.
He says many of them will "fall" first before they grow up.
I don't know if I believe it all, but it is the pattern my WH followed.
As for his dating history, I would say he was late to the game, as he did not start until college and then married his college sweetheart and then divorced shortly thereafter. I don't think he ever had the skills with any of his relationships including our marriage.
I still get mad that we could have resolved his issues with one conversation, instead he has an A to boost his ego.