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This chapter highlights several challenges faced by author on a dilemma during his introduction to social issues class. First, issues of freedom of speech can arise in classroom discussions on controversial social issues. Second, the dilemma highlights the experiences of marginalized students when individuals use" free speech" to justify prejudicial comments. Third, the dilemma demonstrates the heightened consequences that students experience when inhabiting a solo status in the classroom. The chapter begins by reflecting on these challenges and considers how context and intersectionality informs them. It then proposes best practices for resolving the dilemma, which involves techniques within the classroom but also requires structural changes to institutions of higher education, particularly in the United States context where this dilemma occurred. Even with best pedagogical practices in the classroom …