Gay men's health researchers in North America have recently attended to sexual and mental health issues affecting ethnic minority men, many of whom are also immigrants. Most of this work is grounded in epidemiological models that focus on relationships between individual HIV risk and sexual behaviors. Consequently, they the frame the sexual health of gay and bisexual immigrants as the product of cultural issues (for example, family and religious homophobia, lack of health education) or gay community issues (prevalence of drug use and casual sex) that lead to self‐devaluation, depression, and unprotected sex with multiple partners. Few studies, however, examine these phenomena through the lens of migration and resettlement. Using the narratives from twelve in‐depth interviews with settlement and AIDS Service Organization (ASO) workers in Toronto, Ottawa, and London, Ontario, Canada, this article examines four types of post‐migration urban encounters that influence sexual health: negotiations of resettlement‐related stress, encounters with the urban gay community, encounters with the online gay community, and encounters with sexual health promotion itself. The findings suggest that these encounters are important intervening events that mediate the relationship between the attributes of the immigrant and his sexual health behaviors and outcomes.