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As the number of youths using the Internet regularly increase, so too does the number of youths potentially vulnerable to negative experiences online. Clinicians, policy makers, and parents need to better understand the Internet and factors related to positive and negative experiences online. OBJECTIVE: Primarily to investigate the association between youth-reported depressive symptomatology and unwanted Internet sexual solicitation and secondarily to identify sex differences in related characteristics of affected youth. METHODS: Data from the Youth Internet Safety Survey were analyzed to investigate the association between reported depressive symptomatology and unwanted Internet sexual solicitation. The Youth Internet Safety Survey was a nationally-representative, cross-sectional telephone survey. Youth participants (N = 1501) were English speakers between the ages of 10 and 17 years who had accessed the Internet at least 6 times in the previous 6 months and had resided in the household for at least 2 weeks in the previous year. Eighty-two percent of contacted households agreed to participate. Each participant was asked to indicate whether any of the 9 symptoms of major depression defined by the Diagnostic and Statistical Manual of Mental Disorders, Fourth Edition (DSM-IV) had been present within the previous month. Logistic regression was used to estimate the odds of reporting an unwanted sexual solicitation online for youths with mild or major depressive symptomatology versus no symptomatology. A parsimonious, multivariate model of significant youth characteristics was identified separately for males and females. RESULTS: Youths who report major depressive-like symptoms were 3.5 times more likely (odds ratio, 3.54; 95% confidence interval, 2.19-5.71) to also report an unwanted sexual solicitation online compared to youths with mild/no symptomatology. After adjusting for significant Internet and psychosocial characteristics, male Internet users who report major depressive-like symptomatology were 2.5 times more likely to also indicate an unwanted Internet solicitation (adjusted odds ratio, 2.72; 95% CI, 1.15-6.40); significant differences were not observed among otherwise-similar females. Further, among youths reporting an Internet solicitation (N = 283), youths with major depressive-like symptomatology were twice as likely to report feeling emotionally distressed by the incident compared to youths with mild/no symptomatology (odds ratio, 2.27; 95% CI, 1.03-5.02). CONCLUSIONS: While the majority of youths report positive experiences online, some youths may be more vulnerable to negative experiences. Cross-sectional results indicate that the report of depressive symptomatology is significantly related to the concurrent report of an unwanted Internet sexual solicitation, especially for young males. Future research should focus on parsing out the temporality of events and identifying additional populations of vulnerable youths online.