The increasing phenomenon of cyberbullying among adolescents needs parental, educational, and social intervention. The study aimed to identify the prevalence of cyberbullying among Romanian adolescents and the importance of gender, family-related factors, self-esteem, and parental styles in both victims and perpetrators. A total of 835 adolescents aged 10–19 years were included in the research. An online questionnaire was specially constructed for this research, gathering socio-demographic and family-related data along with information about cyberbullying as a victim, aggressor, or bystander, and strategies used in order to deal with it. Four psychological scales were used to evaluate self-esteem, loneliness, cybervictimization/cyberaggression, and parental style. (3) Results showed that the most common age for a personal smartphone is M = 10.24 ± 2.43. The main reasons why students use these networks are primarily chatting and fun and less for academic tasks. During the week, adolescents spend 5.53 ± 2.75 h on social media, while during weekends, the duration of smartphone usage almost doubles. Girls are the most common victims of cyberbullying, and less than three-quarters of students believe that aggressors can be both girls and boys, and only a quarter of them have reported an incident. Family affluence, the relationship with parents and classmates, the presence of loneliness and sociodemographic factors were found to be in a strong relationship with the presence of aggression and/or victimization among adolescents. Cyberaggression was found to be positively correlated with the aggressive parental style and negatively correlated with the compassionate and avoidant parental styles. Results are crucial for identifying cyberbullying actors and preventing the negative effects of cyberbullying on psychological, social, and academic life for students, parents, and teachers.