6 decades books

A graduating high school boy set on a journey to grow up, to overcome his past fears of loneliness with the help of a mysterious girl who has taken a liking to him. However, only conflicts and bad luck are attracting to him. As he realizes the full capability of the unknown world, he strives to survive with the knowledge he comes across with, and Death would only wait by the fool''''s door as he encounters many more problematic figures. Would he someday come to a resolve, or despair for eternity?