1. He never really learned about relationships.
This has always surprised me. People (men and women) spend years of their life learning about business, history, science, and whatever subject comes our way. But when it comes to the one thing every single one of us shares — relationships — many are generally clueless.
Time is not taken to observe, talk to, or learn about the opposite sex. The more effort you put into learning about women, particularly the one in your life, the more likely you are to be in tune with her feelings, emotions, likes and dislikes.
This will, of course, lead to a smoother, happier relationship because you can anticipate her wants and needs in order to act on them. You don't need to be a mind reader; you just need to put in a little effort.
2. He spends too much time trying to sell himself.
You spend far too much time talking about yourself and not enough time learning about her. Dating is not supposed to be a sales pitch where you try to convince the person on the other end of the table that you're their best option.
It's about mutual learning and figuring out whether or not you are both a match for each other. You have two ears and one mouth for a reason, so listen twice as much as you speak.