This study explored adolescents' reasons for involving themselves, or not, in risktaking behavior, in two vulnerable areas of North Jakarta. The sample was purposively selected among households with adolescents ranging from 12 to 18 years old living in the two areas. The study involved 401 parents (8% female; 92% male; mean age 45.3 years) and 414 adolescents (57.49% female; 42.51% male; mean age 14.9 years). Parents' demographic data included educational level, employment status, family income, and expenditure. Adolescents were asked about their perceptions of their relationships with their parents, whether they had been involved in eight risky behaviors (smoking, consuming alcohol, substance use, brawling, crime, physical fighting, heavy petting, and premarital sex), and reasons for engaging in risky behaviors or not. The comparison of proportions of eight risky behavior was tested by different test procedures, namely Z test, Chi-Square and Marascuillo multiple comparison. Results revealed that older adolescents were more likely to be involved in risk-taking, and boys were more likely to engage in risky behaviors than girls. The study also indicated that curiosity and peer pressure were the main reasons adolescents engaged in risky behaviors. Advice from family members, fear of God, and fear of being sinful were reasons adolescents did not engage in risky behaviors.