NON-FICTION that will help me understand a young man’s struggles AND FICTION that will help a young man with his struggles, something he can relate to.

Hello, soon I'm about to be an important person in a 17 y/o boy's life and I need advice.

I have a rich experience with young women's struggles but I need guidance to gain a similar understanding of a young man's struggles and needs in the nowadays world.

A fiction book for him to understand himself better would also be most appreciated.