The present study reports frequency rates of cybergrooming, profiled characteristics of cybergrooming perpetrators, and examine direct and indirect associations between cyberbullying victimization, self-esteem, and cybergrooming victimization. The study sample included 2,162 adolescents between 11 and 19 years from three Western (Germany, the Netherlands, the United States) countries and one Southeast Asian country (Thailand). Across countries, 18.5% of participants reported having had contact with a cybergroomer. Western girls, as compared to boys, were at greater risk to have been contacted by a cybergroomer. No significant sex difference was found for Southeast Asian adolescents. Also, Southeast Asian adolescents reported higher rates of cybergroomer contact as compared to Western adolescents. Cybergroomers were most often males and older than victims. Both cyberbullying victimization and low self-esteem increased the probability of coming into contact with a cybergroomer, and self-esteem mediated the effects of cyberbullying victimization on cybergrooming victimization. The results are discussed in relation to practical implications and future research.