Background: Divorce experience (DE) may cause health and self-conceptual problems, but these consequences might also be caused by conflicts and lack of conversational confidence (CC) with one or both parents. We investigated how DE impacted CC and how DE and CC impacted health complaints and self-esteem in a two-year longitudinal cohort study. Methods: The study was performed between 2011 and 2013 among 1225 students in junior high school (aged 11 and 13 years in 2011). We used binary logistic analyses to account for how DE impacted CC, and linear regression analyses to examine how DE and CC impacted on subjective health and self-esteem in 2013. Results: The study revealed that former and recent DEs impacted CC with fathers only. The impact was most evident for the more severe forms of conversational difficulties. DE in itself predicted only self-esteem, and CC with parents mediated this association. CC with both mothers and fathers had strong temporal causal associations with the outcomes two years later. Only CC with fathers impacted changes of the health complaints and self-esteem in full-model residual change analyses. Conclusions: The study proves a sex-specific effect on loss of CC between fathers and children after divorce. The impairment of CC has predictive repercussions on the health and self-conception of adolescents in their middle teenage years. From a public-health perspective, preserving the relation and the confidence between children and their fathers after divorce seems an important task.