This study investigated the influence of parental emotional support on adolescent self-esteem, emotional intelligence and adolescents’ happiness along with the possible mediating effects of emotional intelligence and self-esteem between parental emotional support and adolescent happiness. In addition, it explored whether the relationship among the variables differs according to the gender of parents and adolescents. Data were collected from 278 Korean high school students (140 males and 138 females). Multi-group structural equation modeling analyses were used to analyze the data. The results indicated that parental emotional support did not directly affect adolescent happiness, but rather influenced it indirectly through the mediating effect of self-esteem. While both maternal and paternal emotional support had a positive influence on self-esteem, only maternal emotional support had a significant impact on emotional intelligence, indicating that parental emotional support may have different influences on adolescent emotional intelligence according to the parents’ gender. The results also indicated that maternal/paternal emotional support may have a different impact according to adolescents’ gender. For male adolescents, only paternal emotional support affected happiness through self-esteem. For female adolescents, both maternal and paternal emotional support exerted a significant influence on happiness via self-esteem, whereas maternal support had a direct influence on all other variables.