Background: The purpose of this study was to examine parent report of conversations about difference and disability in families of adolescents with intellectual disability. Materials and Methods: Participants included 50 parents (44 mothers, four fathers, and two other caregivers) and their adolescents with intellectual disability (M age = 15.9). Parents provided written responses to open-ended questions regarding conversations with their adolescent. Adolescents completed measures of self-concept and self-determination. Results: The majority (66%) of parents reported talking to their adolescent about difference and/or disability. Consistent with previous research, some of these conversations were in response to social exclusion (e.g. child was bullied). Parents who knew the aetiology of their child's disability were significantly more likely to talk with their child about his or her disabling condition. Conclusions: Parents' narratives illustrate their struggle to explain disability to their adolescent. Professionals are challenged to consider how to promote proactive conversations between parents and adolescents.