Orenstein explains her rationale for writing the book in the first place. Having spent her career focusing on girls' issues, Orenstein admits that she never imagined that she would devote an entire book to boys. In the aftermath of the #MeToo movement, however, she saw a need to address masculinity, particularly as it relates to sex. Orenstein writes: "If I truly wanted to promote safer, more enjoyable, more egalitarian, more humane sexual relationships among young people, I needed to go back into [the world of teenage boys] and have the other half of the conversation" (2).

She also explains her process for the book, which included over a hundred interviews with teenage boys of various backgrounds and experiences. During her conversations she found an incredible amount of openness and candor, even around subjects like porn and casual sexual encounters. Orenstein's interviews spanned over two years. She focused on young males aged 16 to 22 and changed the names of her subjects to protect their privacy. Her primary goal was not to confirm an existing bias, but to genuinely listen.

Orenstein explains her methodology. She is not an academic who specializes in psychology, but a journalist seeking truth by means of individual stories.