This dissertation explores the tension between the rise of the anti-bullying movement and the persistent marginalization of LGBTQ, low income, and racial minority youth in U.S. schools. Today, all 50 states have passed anti-bullying laws and most schools have anti-bullying policies in place to protect youth from conflict, yet there is minimal data on the outcomes of these initiatives on school communities. Drawing on two years of fieldwork at a rural high school in the Northeast, social media observations, 127 interviews, and analysis of bullying reports and prevention strategies, I examine these outcomes and how they shape adolescent relationships. I find that while teens’ bullying practices routinely police gender and sexuality norms and target marginalized youth, the initiatives designed to prevent bullying do not address the larger inequalities that motivate and structure teen conflicts. Instead, they individualize bullying and emphasize tolerance. I argue that anti-bullying’s “culture of tolerance” reinforces existing gender, class, sexual, and racial hierarchies among youth, and makes bullying more diffuse and difficult to manage. While these campaigns may appear successful on the surface, particularly among privileged students, they often obscure the processes by which inequality is maintained in school settings, and inadvertently produce inequalities themselves. Ultimately, I find that youth have more effective anti-bullying strategies, collectively going beyond tolerance to use social media as a site for resistance, recognition, and diversity education.