The impact of countervailing social network influences (i.e., pro-social, anti-social or HIV risk peers) on problem behaviors (i.e., HIV drug risk, HIV sex risk or anti-social behaviors) among 696 homeless youth was assessed using structural equation modeling. Results revealed that older youth were less likely to report having pro-social peers and were more likely to have HIV risk and anti-social peers. A longer time homeless predicted fewer pro-social peers, more anti-social peers, and more HIV risk peers. Heterosexual youth reported fewer HIV risk peers and more pro-social peers. Youth recruited at agencies were more likely to report pro-social peers. Having pro-social peers predicted less HIV sex risk behavior and less anti-social behavior. Having HIV risk peers predicted all problem behavior outcomes. Anti-social peers predicted more anti-social behavior. Once the association between anti-social and HIV risk peers was accounted for independently, having anti-social peers did not independently predict sex or drug risk behaviors.