This study explores the effects of romantic involvement and dating behaviors on adolescent academic and psychosocial functioning in Chinese societies, where adolescent dating is generally discouraged and believed to bear adverse outcomes. Adolescents (male = 48.6%; Mean Age = 15.20 years) from Taiwan (N = 1,081) and Mainland China (N = 684) were recruited through stratified sampling to complete self-report surveys oned their academic performance, depressive symptoms, self-esteem, relationship status, and gender-role beliefs. Adolescents with current or past dating experiences were also asked about specific dating behaviors such as onset of dating, number of relationships, and breakup experiences. Approximately one-third of Chinese adolescents surveyed have past or ongoing dating experience, who showed poorer academic performance and mental health outcomes than never-dated teens. Currently single adolescents with past dating experiences showed the greatest depressive symptoms. Dating experiences also seem to promote boys' self-esteem but dampen girls' self-esteem. Early dating, over-dating, sexual activities, and breakup experiences could undermine adolescents' academic and psychosocial well-being, especially for girls. These findings have significant implications for practice and policy regarding adolescent education and mental health.