In this chapter—"Heads You Lose, Tails I Win: Boys of Color in a White World"— Orenstein chronicles the experiences of young men of color within the context of predominantly white institutions. She tells the story of Xavier, an African American college student who constantly questions his place in the predominantly white college he attends. Xavier is fully aware of his identity as a Black male, which means that he must proceed cautiously within the white environment. He shares the following insight: "It was almost like I needed to show other people who've subscribed to a lot of popular black culture that there's more to us than what they see in videos" (139).

Orenstein states that "the politics of race, attraction, and love are complex" (147). She tells the stories of Spencer, an Asian American man who finds himself more attracted to white girls than Asian girls, and Mauricio, the son of Ecuadorian immigrants who feels lonely and disconnected in his predominantly white environment. Orenstein anchors the chapter in the complexity of cultural and racial diversity within the umbrella of sex. She is aware that the systemic factors that have historically marginalized young men of color inevitably shape their sex lives.