It is widely accepted that sexual minority youth (SMY) are subjects of homophobic bullying and homophobic victimization, and they are at higher risk for psychological distress compared to their heterosexual counterparts. Meyer (2003) introduced the minority stress conceptual framework to explain this increased prevalence and its effects. The minority stress conceptual framework proposed that the lesbian, gay, and bisexual (LGB) population is subjected to additional stressors due to its minority status which results in increased psychological distress. The problem addressed in this study was the high incidence of bullying, harassment, social isolation, and violence against SMY, those questioning their sexual identity, and those perceived to be LGB in a large metropolitan school district in South Florida. The purpose of this comparative study was threefold: to compare risk factors for students in Grades 9-12 (a) who identified as LGB to those who identified as heterosexual (straight), (b) who identified as LGB to those who identified as questioning, and (c) who perceived that others identified them as LGB compared to those who did not perceive that others identified them as LGB at a large metropolitan school district in the southeastern United States. Data from the 2015 National Youth Risk Behavior Survey (YRBS) was used to further examine how these risk factors, including alcohol and other drug use and abuse, psychological distress, violence, and sexual behaviors, interacted to influence health disparities among youth in Grades 9 to 12 impacted by homophobic bullying. Mann-Whitney U analyses were conducted to detect the differences in health risk behaviors and outcomes among heterosexual and LGB students. Also, logistic regression models were used to examine any sexual identity effects involved in the association between being bullied and health risk behaviors. Findings indicated that students who identified as LGB or gender nonconforming, or who reported being teased because of their perceived sexual orientation (PSO) were at greater risk for negative health outcomes and negative health risk behaviors. More specifically, identification as LGB or gender expansive, or being teased because of PSO was predictive of psychological distress, suicidal ideation, and sexual, alcohol, and drug risk behaviors. This study extends research on risky behaviors among youth who were bullied due to PSO and provides a new perspective on how homophobic victimization may influence these youth’s risk-taking behaviors and health disparities.