This study aimed to investigate how “outness,” spirituality/religiosity, gay identity affirmation and demographic factors relate to each other and predict internalized homophobia (IH). IH is linked to a host of negative outcomes. The study took place over three months at the 2012 New York Pride parades in all five boroughs. Participants were recruited via the cross-sectional street-intercept approach, 195 of whom met the inclusion criteria. Data were analyzed using SPSS 26. In sum, the sample consisted of a highly educated, mostly white, high-income subset of men. The regression model indicated that gay identity importance and being “out” to world were predictive of IH. There were also significant differences in participation in gay activities along the lines of education and race. Same sex attracted men who earned a four-year college degree reported more participation in gay activities compared to those of lower attainment levels. Compared to White men, Latino men participated in less gay activities, possibly due to cultural factors. Men who have higher levels of affirmation were more likely to participated in gay activities, which could include pride, which suggests a potential bias. Buddhists reported unusually high levels of internalized homophobia compared to other spiritual and religious practices and orientations. Finally, there were no significant differences in homophobia with race, but there was one with religion. Christians exhibited statistically significantly higher levels of internalized homophobia compared to those who were nonreligious namely atheists, agnostics, and the spiritual but not religious. Implications for health promotion were discussed.