Throughout the book, Orenstein draws attention to the phenomenon of toxic masculinity. She explains how the #MeToo movement articulated how masculinity was fundamentally broken. High-profile examples of predatory behavior came to light, such as in the examples of Harvey Weinstein, Bill Cosby, Kevin Spacey, Louis C.K., Matt Lauer, and former president Donald Trump. In the wake of this, Orenstein was motivated to write a book that could serve as "an opportunity to engage young men in authentic, long-overdue conversations about gender and intimacy" (2).

In her interviews, Orenstein often encountered young men who were intellectually opposed to toxic masculinity, but who in practice were generally unwilling to challenge the status quo in a meaningful way. Her conversations with Cole, for instance, shed light on the dilemma that many teenage boys face—either stand up to your peers and run the risk of losing your social belonging, or passively allow expressions of toxic masculinity, such as bragging about sexual conquests, to flow free in your midst.

This dilemma was common for many of Orenstein's subjects. They shared that the expectation for males, even from a young age, is to stifle

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