If your boyfriend works on improving himself as a person, he will experience a boost in self-esteem, which will make him feel more "deserving" of a good catch.

Does he engage in any activity that allows him to view himself as a good, worthy person? Is he educated?

Also, I think insecurity is a symptom of youth, and to a large extent one outgrows a certain amount of this, assuming a normal process of maturing...

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