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To determine the prevalence of age-bridgers among urban males aged 14–24 years, asymptomatically infected with chlamydia and to determine factors that distinguish age-bridgers from non age-bridgers. An index was defined as an age-bridger if within 2 months, he had had at least two sexual partners who differed from him in age by ≥2 years.Infected males provided data about themselves and up to four sexual partners in the past 2 months. Bivariate and multivariable logistic regression was used in the analysis.The prevalence of age bridging was 21% in Baltimore and 26% in Denver. In both cities, in bivariate analysis, age-bridgers and their partners engaged in significantly more risky sexual behaviours. In adjusted multivariable analysis after controlling for number of sexual partners, age bridging was associated with having a sexual partner in the past 2 months, who, at time of last sexual intercourse, was drinking.Age-bridgers represented major proportions of the study populations and, along with their sexual partners, were more likely to engage in risky sexual behaviours. Male age-bridgers may be key players in the transmission of sexually transmitted infections among youth linking age-disparate sexual networks.