Asperger syndrome (AS) and high functioning autism are complex developmental disabilities that have a significant impact on the individual and his/her family. Asperger syndrome is characterized by challenges with understanding non-verbal communication, difficulties with social relationships, and restricted interests. Having a brother or sister with AS has the potential to impact the development of a sibling. This study explored the overall experience of having a brother or sister with AS, with a specific focus on how issues of grief and loss experienced by the sibling may have implications for developmental transitions. The study employed a qualitative model of inquiry using three layers of interviewing. The middle layer of interviewing was used to seek outsiders’ opinions in an effort to deal with validity threats and to enrich the focus of the final layer of interviews. Interview data revealed themes of parentification, impact on social relationships, impact on vocational choices, and an expression of grief and loss through a comparison of the cognitive schema of the “normal” family.