ABSTRACT. Given the voluntary nature of adolescent friendships, forgiveness of interpersonal transgressions has been identified as a critical aspect of maintaining these relationships. However, transgression forgiveness is related to a range of situational (e.g., transgression severity), interpersonal (e.g., friendship commitment), and intrapersonal (e.g., victim's empathy) factors. Data from 161 adolescents were used to examine the nature of the relationships between these factors and forgiveness and to examine the differential association patterns for adolescent boys and girls. Results for the overall adolescent sample indicated both situational and interpersonal factor associations with forgiveness (R2 = .52, p < .001). Examination of separate female and male forgiveness reports indicated similar interpersonal factor associations and differential situational factor associations with female (R2 = .46, p < .001), and male (R2 = .60, p < .001) forgiveness. Findings suggest the likelihood of forgiving may be contextually dependent, and that researchers should consider transgression, relationship, and intrapersonal characteristics when examining forgiveness. Further, the present study suggests the contextual factors associated with forgiveness may be further differentiated by gender.