<p>Who will turn to chatbots for emotional disclosure? This research contributes to ongoing scientific efforts to understand chatbot usage behaviors among adolescents. Specifically, we examined the relationships between self-disclosure to chatbots and levels of self-compassion and existential meaninglessness, as well as whether gender and culture moderate these preferences. A cross-cultural survey study was conducted to pursue this goal. A total sample of 2272 adolescents (M age = 15.53&#xa0;years) from the United States and Hong Kong was collected. A major finding was that the preference for self-disclosure with chatbots was positively correlated with levels of self-compassion and negatively correlated with levels of existential meaninglessness. These correlations were moderated by gender and culture. The results also indicated that adolescents who exclusively self-disclose to chatbots may experience a higher level of existential meaninglessness. These new findings present opportunities for future studies that will enhance our understanding of the relationship among self-disclosure to chatbots, self-compassion and existential meaninglessness.</p>