This study compares online self-disclosure through Facebook with offline self-disclosure through face-to-face interactions to understand when and why digital natives may prefer to resolve perceived loneliness by turning to the Internet. Survey data from adolescents indicate that digital natives who employ passive coping favor self-disclosure through Facebook, but natives who engage in active coping prefer face-to-face self-disclosures. Both routes, through active and passive coping, appear to mediate the relationship between loneliness and online/offline self-disclosures. Moreover, the relationship between loneliness and self-disclosure exhibits gender differences. This study extends insights into digital natives, sheds light on self-disclosures, and contributes to coping research.