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Despite the large body of extant literature on sexually transmitted infections (STIs) in adolescents and young adults (AYAs), more research on social and environmental contextual factors is needed. Also, further examination of STI indicators by gender remains a critical area of research focus.Anonymous survey data were collected using audio computer-assisted self-interviews in community venues in urban, low-income, STI prevalent, US neighborhoods to reach AYAs, aged 12 to 24 years. Conventional descriptive statistics, bivariate analysis, and multiple logistical regression models were used to assess indicators of a self-reported lifetime prevalence of STIs.Participants (N = 1540) were on average 20.6 years; 57.2% were women, the majority were racial and ethnic minorities (92%), and almost half (49.2%) identified as sexual minorities. Nearly one third (32.%) had 1 or more STIs. As expected, gender differences were identified. For AYA men, being African American/Black, moving residences more than 4 times since kindergarten, and having a history of human immunodeficiency virus testing were each positively associated with STIs. Also, those who strongly disagreed that many young people in their community exchanged sex for money had a significantly lower likelihood of having an STI. For AYA women, exchanging sex for drugs or money, lacking money, which prevented activities, and using marijuana were each associated with STIs.This research extends our understanding of social and environmental contextual influences on AYAs’ risk for STIs. It highlights differences in risk exposures that are distinctly different for AYA women and men, suggesting the need for tailored interventions to address their unique economic needs and social challenges.