This study aims to examine the link between male perpetration of teen dating violence (TDV) and neighborhood violence, as well as associations with gender attitudes and perceived peer and neighborhood norms related to violence among a sample of urban adolescent boys. Participants of this cross-sectional study (N = 275) were between the ages of 14 and 20 years and recruited from urban community health centers. Crude and adjusted logistic and linear regression models were used to examine TDV perpetration in relation to (a) neighborhood violence involvement, (b) perceptions of peer violence, (c) perceptions of neighborhood violence, and (d) gender attitudes. Slightly more than one in four (28%) boys reported at least one form of TDV perpetration; among boys who have ever had sex, almost half (45%) reported at least one form of TDV perpetration. In logistic and linear regression models adjusted for demographics, boys who reported TDV perpetration were more likely to report involvement in neighborhood violence (odds ratio (OR) = 3.1; 95% confidence interval (CI) = 1.7-5.5), beliefs that their friends have perpetrated TDV (OR = 2.7; 95%CI = 1.4-5.1), perceptions of violent activity within their neighborhood (OR = 3.0; 95%CI = 1.4-6.3), and greater support of traditional gender norms (β = 3.2, p = 0.002). The findings suggest that efforts are needed to address boys' behaviors related to the perpetration of multiple forms of violence and require explicit efforts to reduce perceived norms of violence perpetration as well as problematic gender attitudes (e.g., increasing support for gender equity) across boys' life contexts.