The present study used data from the SAFT (Safety, Awareness, Facts and Tools) Singapore survey, a national survey of 1,124 youths aged 12-17, to explore the issue of risk on the Internet. We investigated factors that influence adolescents' engagement in risky Internet behavior, in particular, meeting face-to-face someone they first encountered online. The adolescents ranged from ages 12 to 17, with a mean of 14.32 (SD = 1.37); 49.6% of the adolescents were girls. The study utilized a 93-item survey that was part of the SAFT Project. Results indicated that 16% of adolescent Internet users in Singapore have had a face-to-face meeting with someone first encountered online. The following factors were found to be predictors of adolescents engagement in such face-to-face meetings: age, frequency of Internet use, frequency of chatting and gaming behavior, parental rules, type of personal information given out, amount of inappropriate messages received, whether inappropriate websites have been visited, and type of internet advice heard. Implications of the results are discussed.