The first chapter—"Welcome to Dick School"—focuses mostly on Cole, a white straight college athlete. Cole sheds light on the toxic masculinity that often manifests in locker rooms. While Cole is aware that hyper-masculine "bro culture" stems from and perpetuates toxic ideologies, he was mostly unwilling to speak up. As Cole explains, you risk social ostracism if you speak up against a male peer or teammate's bragging about sexual conquest.

Orenstein contextualizes masculinity in terms of emotional health. From a young age, boys learn to suppress their emotions and are taught that emotional vulnerability is a sign of weakness associated with femininity. As Orenstein writes: "Love, connection, and vulnerability are signs of weakness; aggression is celebrated and eroticized; conquest is everything" (13). Within this narrow definition of masculinity, boys like Cole are expected to maintain the status quo. Others, such as Mateo and Adam, who are openly gay, struggle to find an identity that allows them to flourish as human beings.

This chapter focuses on the effects of toxic masculinity. For young men like Cole, they have to choose between social acceptance and speaking up for their own beliefs on how women should be treated.