A large body of literature provides support for the role of empathy as a prominent factor in socio-emotional development and functioning. Although deficits in empathy are known to associate with maladaptive behaviors, less literature documents the effects of excessive empathy, which has been found to relate to various internalizing problems such as depression. There are two types of empathy, cognitive and affective, which manifest themselves in different ways and thus, have differential effects on outcomes. Therefore, in a sample of 724 Belgian adolescents (Mage = 13.83 ± .96), the present study sought to elucidate the effects of cognitive and affective empathy on depressive symptoms and self-esteem. We also explored the interactive effects of empathy and adolescent perceived mother–child relationship quality in the prediction of our outcomes. Results revealed affective and cognitive empathy predicted outcomes concurrently, with affective empathy predicting more maladaptive outcomes and cognitive empathy predicting more positive outcomes. Interaction effects emerged between affective empathy and the relationship quality indicators. However, no interactions occurred with cognitive empathy. Further, longitudinal data revealed only cognitive empathy had long-term effects (predicting positive outcomes such as lower levels of depression and higher levels of self-esteem) suggesting that cognitive empathy may be a protective factor. Limitations and suggestions for future research are discussed.